Frode Rise

• Hvinden, Ingvild Comfort; Berg, Henriette Engen; Sachse, Daniel; Skaga, Erlend; Skottvoll, Frøydis Sved; Lundanes, Elsa; Sandberg, Cecilie; Vik-Mo, Einar O.; Rise, Frode & Wilson, Steven Ray Haakon (2019). Nuclear Magnetic Resonance Spectroscopy to Identify Metabolite Biomarkers of Nonresponsiveness to Targeted Therapy in Glioblastoma Tumor Stem Cells. Journal of Proteome Research.  ISSN 1535-3893.  18(5), s 2012- 2020 . doi: 10.1021/acs.jproteome.8b00801
• Murray, J Sam; Selwood, Andrew I.; Harwood, D Tim; van Ginkel, Roel; Puddick, Jonathan; Rhodes, Lesley L; Rise, Frode & Wilkins, Alistair L. (2019). 44-Methylgambierone, a new gambierone analogue isolated from Gambierdiscus australes. Tetrahedron Letters.  ISSN 0040-4039.  60(8), s 621- 625 . doi: 10.1016/j.tetlet.2019.01.043
• Nytoft, Hans Peter; kildahl-Andersen, Geir; Lindstrøm, Sofie; Rise, Frode; Bechtel, Achim; Mitrovic, Danica; Dokovic, Natasa; Zivotic, Dragana R. & Stojanovic, Ksenija A (2019). Dehydroicetexanes in sediments and crude oils: Possible markers for Cupressoideae. Organic Geochemistry.  ISSN 0146-6380.  129, s 14- 23 . doi: 10.1016/j.orggeochem.2019.01.001
• Pang, Di-Jiang; Huang, Chao; Chen, Mei-Ling; Chen, Yu-Long; Fu, Yu-Ping; Paulsen, Berit Smestad; Rise, Frode; Zhang, Bing-Zhao; Chen, Zheng-Li; Jia, Ren-Yong; Li, Li-Xia; Song, Xu; Feng, Bin; Ni, Xue-Qin; Yin, Zhong-Qiong & Zou, Yuan-Feng (2019). Characterization of Inulin-Type Fructan from Platycodon grandiflorus and Study on Its Prebiotic and Immunomodulating Activity. Molecules.  ISSN 1420-3049.  24(7) . doi: 10.3390/molecules24071199
• Samuelsen, Anne Berit C.; Rise, Frode; Wilkins, Alistair L.; Teveleva, Lioubov; Nyman, Anna Armika Tussilago & Aachmann, Finn Lillelund (2019). The edible mushroom Albatrellus ovinus contains a α-L-fuco-α-D-galactan, α-D-glucan, a branched (1→6)-β-D-glucan and a branched (1→3)-β-D-glucan. Carbohydrate Research.  ISSN 0008-6215.  471, s 28- 38 . doi: 10.1016/j.carres.2018.10.012 Vis sammendrag

  Albatrellus ovinus, the sheep polypore, is a large, dense mushroom being rich in cell wall material. Polysaccharides were isolated by sequential extraction, enzymatic treatment and analyzed with respect to monosaccharide composition, glycosidic linkages by methylation and GC-MS as well as NMR spectroscopy. A fucogalactan composed of an (1→6)-α-D-galactan backbone with single α-L-Fucp residues attached at O-2 was identified in the hot water extract obtained after treatment with a protease and size exclusion chromatography. Both the hot water extract and the hot alkali extract contained an (1→4)-α-D-glucan whereas β-D-glucans were mainly present in the latter. Structural analysis suggested the presence of two different β-D-glucan backbone structures; a (1→6)-linked β-D-glucan with single β-D-Glcp residues at O-3 and also a (1→3)-linked β-D-glucan with branches in O-6. In addition there were identified short (1→2)-linked β-D-xylan and (1→3)-α-D-mannan chains.

• Foss, Amanda; Miles, Christopher Owen; Samdal, Ingunn Anita; Løvberg, Kjersti Eriksen; Wilkins, Alistair Lawrence; Rise, Frode; Jaabæk, Jon Atle Hoff; McGowan, Peter C & Aubel, Mark T (2018). Analysis of free and metabolized microcystins in samples following a bird mortality event. Harmful Algae.  ISSN 1568-9883.  80, s 117- 129 . doi: 10.1016/j.hal.2018.10.006
• Kenton, Nathaniel T.; Adu-Ampratwum, Daniel; Okumu, Anthony A.; McCarron, Pearse; Kilcoyne, Jane; Rise, Frode; Wilkins, Alistair Lawrence; Miles, Christopher Owen & Forsyth, Craig J. (2018). Stereochemical Definition of the Natural Product (6R,10R,13R, 14R,16R,17R,19S,20S,21R,24S,25S,28S,30S,32R,33R,34R,36S,37S,39R)-Azaspiracid-3 by Total Synthesis and Comparative Analyses. Angewandte Chemie International Edition.  ISSN 1433-7851.  57(3), s 810- 813 . doi: 10.1002/anie.201711008
• Kenton, Nathaniel; Adu-Amprawum, Daniel; Okumu, Anthony A.; Zhang, Zhingao; Chen, Yong; Nguyen, Son; Xu, Jianyan; Ding, Yue; McCarron, Pearse; Kilkoyne, Jane; Rise, Frode; Wilkins, Alistair Lawrence; Miles, Christopher Owen & Forsyth, Craig J. (2018). Total Synthesis of (6R,10R,13R,14R,16R,17R,19S,20R,21R,24S, 25S,28S,30S,32R,33R,34R,36S,37S,39R)-Azaspiracid-3 Reveals Non-Identity with the Natural Product. Angewandte Chemie International Edition.  ISSN 1433-7851.  57(3), s 805- 809 . doi: 10.1002/anie.201711006
• Kilcoyne, Jane; McCarron, Pearse; Twiner, Michael J.; Rise, Frode; Hess, Philipp; Wilkins, Alistair Lawrence & Miles, Christopher Owen (2018). Identification of 21,22-Dehydroazaspiracids in Mussels (Mytilus edulis) and in Vitro Toxicity of Azaspiracid-26. Journal of natural products.  ISSN 0163-3864.  81(4), s 885- 893 . doi: 10.1021/acs.jnatprod.7b00973
• Morland, Cecilie; Frøland, Anne-Sofie; Nguyen, Mi Mong Tran; Storm-Mathisen, Jon; Gundersen, Vidar; Rise, Frode & Hassel, Bjørnar (2018). Propionate enters GABAergic neurons, inhibits GABA transaminase, causes GABA accumulation and lethargy in a model of propionic acidemia. Biochemical Journal.  ISSN 0264-6021.  475(4), s 749- 758 . doi: 10.1042/BCJ20170814
• Furse, Samuel Robert; Jakubec, Martin; Rise, Frode; Williams, Huw E.; Rees, Catherine E.D. & Halskau, Øyvind (2017). Evidence that Listeria innocua modulates its membrane's stored curvature elastic stress, but not fluidity, through the cell cycle. Scientific Reports.  ISSN 2045-2322.  7:8012, s 1- 11 . doi: 10.1038/s41598-017-06855-z Fulltekst i vitenarkiv. Vis sammendrag

  This paper reports that the abundances of endogenous cardiolipin and phosphatidylethanolamine halve during elongation of the Gram-positive bacterium Listeria innocua. The lyotropic phase behaviour of model lipid systems that describe these modulations in lipid composition indicate that the average stored curvature elastic stress of the membrane is reduced on elongation of the cell, while the fluidity appears to be maintained. These findings suggest that phospholipid metabolism is linked to the cell cycle and that changes in membrane composition can facilitate passage to the succeding stage of the cell cycle. This therefore suggests a means by which bacteria can manage the physical properties of their membranes through the cell cycle.

• Georgiev, Yordan N.; Paulsen, Berit Smestad; Kiyohara, Hiroaki; Ciz, Milan; Ognyanov, Manol H.; Vasicek, Ondrej; Rise, Frode; Denev, Petko N.; Lojek, Antonin; Batsalova, Tsevetelina; Dzhambazov, Balik; Yamada, Haruki; Lund, Reidar; Barsett, Hilde; Krastanov, Albert I.; Yanakieva, Irina Z. & Kratchanova, Maria G. (2017). Tilia tomentosa pectins exhibit dual mode of action on phagocytes as beta-glucuronic acid monomers are abundant in their rhamnogalacturonans 1. Carbohydrate Polymers.  ISSN 0144-8617.  175, s 178- 191 . doi: 10.1016/j.carbpol.2017.07.073
• Georgiev, Yordan N.; Paulsen, Berit Smestad; Kiyohara, Hiroaki; Ciz, Milan; Ognyanov, Manol H.; Vasicek, Ondrej; Rise, Frode; Denev, Petko N.; Yamada, Haruki; Lojek, Antonin; Kussovski, Vesselin; Barsett, Hilde; Krastanov, Albert I.; Yanakieva, Irina Z. & Kratchanova, Maria G. (2017). The common lavender (Lavandula officinalis Mill.) pectic polysaccharides modulate phagocytic leukocytesd and intestinal Peyer´s patch cells. Carbohydrate Polymers.  ISSN 0144-8617.  174, s 948- 959 . doi: 10.1016/j.carbpol.2017.07.011
• Wold, Christian Winther; Kjeldsen, Christian; Corthay, Alexandre; Rise, Frode; Christensen, Bjørn E.; Duus, Jens Øllgaard & Inngjerdingen, Kari Tvete (2017). Structural characterization of bioactive heteropolysaccharides from the medicinal fungus Inonotus obliquus (Chaga).. Carbohydrate Polymers.  ISSN 0144-8617.  185, s 27- 40 . doi: 10.1016/j.carbpol.2017.12.041 Fulltekst i vitenarkiv.
• Miles, Christopher Owen; Sandvik, Morten; Nonga, Hezron Emmanuel; Ballot, Andreas; Wilkins, Alistair Lawrence; Rise, Frode; Jaabæk, Jon Atle Hoff & Loader, Jared I. (2016). Conjugation of Microcystins with Thiols Is Reversible: Base-Catalyzed Deconjugation for Chemical Analysis. Chemical Research in Toxicology.  ISSN 0893-228X.  29(5), s 860- 870 . doi: 10.1021/acs.chemrestox.6b00028
• Nyman, Anna Armika Tussilago; Aachmann, Finn Lillelund; Rise, Frode; Ballance, Simon & Samuelsen, Anne Berit C. (2016). Structural characterization of a branched (1 → 6)-α-mannan and β-glucans isolated from the fruiting bodies of Cantharellus cibarius. Carbohydrate Polymers.  ISSN 0144-8617.  146, s 197- 207 . doi: 10.1016/j.carbpol.2016.03.052 Vis sammendrag

  A comprehensive characterization of polysaccharides from the chanterelle was performed. Experiments included both linkage analysis by methylation and GC–MS, monosaccharide composition analysis by methanolysis, SEC-MALLS and several NMR experiments including COSY, HSQC, TOCSY, HSQC-TOCSY, NOESY, and HMBC. A 671 kDa (1 → 6)-linked α-d-mannan with single and short (1 → 2)-linked side chains (WCcF1b) was isolated from the hot water extract, after protease treatment and fractionation by size exclusion chromatography. The hot 1 M NaOH extract contained two types of β-glucan; a water soluble (1 → 6)-linked β-d-glucan with single and short (1 → 3)-linked β-glucan side chains (ACcSw) and a less branched (1 → 3)-linked β-d-glucan (ACcIw/ACcId), proposed to contain short side chains in O-4. Chemical shifts assignments of the α-mannan and β-glucan are presented as well as chemical shift values obtained from a (1 → 6)/(1 → 3)-β-d-glucan derived from Saccharomyces cerevisiae which was used as reference.

• Nytoft, H. Peter; Vukovic, Nikola S.; Kildahl-Andersen, Geir; Rise, Frode; Zivotic, Dragana R. & Stojanovic, Ksenija A (2016). Identification of a Novel Series of Benzohopanes and Their Geochemical Significance. Energy & Fuels.  ISSN 0887-0624.  30(7), s 5563- 5575 . doi: 10.1021/acs.energyfuels.6b00799
• Nytoft, Hans Peter; Kildahl-Andersen, Geir & Rise, Frode (2016). Unusual hexacyclic oleananes in Late Cretaceous/Tertiary terrigenous oils: NMR characterisation of the major hexacyclic oleanane in Niger Delta oil. Organic Geochemistry.  ISSN 0146-6380.  101, s 196- 206
• Stanic, Ana; Uhlig, Silvio; Sandvik, Morten; Rise, Frode; Wilkins, Alistair Lawrence & Miles, Christopher Owen (2016). Characterization of Deoxynivalenol-Glutathione Conjugates Using Nuclear Magnetic Resonance Spectroscopy and Liquid Chromatography-High-Resolution Mass Spectrometry. Journal of Agricultural and Food Chemistry.  ISSN 0021-8561.  64(36), s 6903- 6910 . doi: 10.1021/acs.jafc.6b02853
• Stanic, Ana; Uhlig, Silvio; Solhaug, Anita; Rise, Frode; Wilkins, Alistair Lawrence & Miles, Christopher Owen (2016). Preparation and Characterization of Cysteine Adducts of Deoxynivalenol. Journal of Agricultural and Food Chemistry.  ISSN 0021-8561.  64(23), s 4777- 4785 . doi: 10.1021/acs.jafc.6b01158
• Hassel, Bjørnar; Elsais, Ahmed; Frøland, Anne-Sofie; Taubøll, Erik; Gjerstad, Leif; Quan, Yi; Dingledine, Raymond & Rise, Frode (2015). Uptake and metabolism of fructose by rat neocortical cells in vivo and by isolated nerve terminals in vitro. Journal of Neurochemistry.  ISSN 0022-3042.  133(4), s 572- 581 . doi: 10.1111/jnc.13079
• Kilcoyne, Jane; Twiner, Michael J.; McCarron, Pearse; Crain, Sheila; Giddings, Sabrina D.; Foley, Barry; Rise, Frode; Hess, Philipp; Wilkins, Alistair Lawrence & Miles, Christopher Owen (2015). Structure Elucidation, Relative LC-MS Response and In Vitro Toxicity of Azaspiracids 7 - 10 Isolated from Mussels (Mytilus edulis). Journal of Agricultural and Food Chemistry.  ISSN 0021-8561.  63(20), s 5083- 5091 . doi: 10.1021/acs.jafc.5b01320
• Stanic, Ana; Uhlig, Silvio; Solhaug, Anita; Rise, Frode; Wilkins, Alistair Lawrence & Miles, Christopher Owen (2015). Nucleophilic Addition of Thiols to Deoxynivalenol. Journal of Agricultural and Food Chemistry.  ISSN 0021-8561.  63(34), s 7556- 7566 . doi: 10.1021/acs.jafc.5b02864 Vis sammendrag

  Conjugation of deoxynivalenol (DON) with sulfur compounds is recognized as a significant reaction pathway, and putative DON–glutathione (DON–GSH) conjugates have been reported in planta. To understand and control the reaction of trichothecenes with biologically important thiols, we studied the reaction of DON, T-2 tetraol, and de-epoxy-DON with a range of model thiols. Reaction conditions were optimized for DON with 2-mercaptoethanol. Major reaction products were identified using HRMS and NMR spectroscopy. The results indicate that thiols react reversibly with the double bond (Michael addition) and irreversibly with the epoxide group in trichothecenes. These reactions occurred at different rates, and multiple isomers were produced including diconjugated forms. LC-MS analyses indicated that glutathione and cysteine reacted with DON in a similar manner to the model thiols. In contrast to DON, none of the tested mercaptoethanol adducts displayed toxicity in human monocytes or induced pro-inflammatory cytokines in human macrophages.

• Kilcoyne, Jane; McCarron, Pearse; Twiner, Michael J.; Nulty, Ciara; Crain, Sheila; Quilliam, Michael A.; Rise, Frode; Wilkins, Alistair Lawrence & Miles, Christopher Owen (2014). Epimers of azaspiracids: Isolation, structural elucidation, relative LC-MS response, and in vitro toxicity of 37-epi-azaspiracid-1. Chemical Research in Toxicology.  ISSN 0893-228X.  27(4), s 587- 600 . doi: 10.1021/tx400434b
• Kilcoyne, Jane; Nulty, Ciara; Jauffrais, Thierry; McCarron, Pearse; Herve, Fabienne; Foley, Barry; Rise, Frode; Crain, Sheila; Wilkins, Alistair Lawrence; Twiner, Michael J.; Hess, Philipp & Miles, Christopher Owen (2014). Isolation, structure elucidation, relative LC-MS response, and in vitro toxicity of azaspiracids from the dinoflagellate azadinium spinosum. Journal of natural products.  ISSN 0163-3864.  77(11), s 2465- 2474 . doi: 10.1021/np500555k
• Langseth, Eirin; Nova, Ainara; Tråseth, Eline Aasen; Rise, Frode; Øien, Sigurd; Heyn, Richard H & Tilset, Mats (2014). A gold exchange: A mechanistic study of a reversible, formal ethylene insertion into a gold(III)-oxygen bond. Journal of the American Chemical Society.  ISSN 0002-7863.  136(28), s 10104- 10115 . doi: 10.1021/ja504554u Vis sammendrag

  The Au(III) complex Au(OAcF)2(tpy) (1, OAcF = OCOCF3; tpy = 2-p-tolylpyridine) undergoes reversible dissociation of the OAcF ligand trans to C, as seen by 19F NMR. In dichloromethane or trifluoroacetic acid (TFA), the reaction between 1 and ethylene produces Au(OAcF)(CH2CH2OAcF)(tpy) (2). The reaction is a formal insertion of the olefin into the Au–O bond trans to N. In TFA this reaction occurs in less than 5 min at ambient temperature, while 1 day is required in dichloromethane. In trifluoroethanol (TFE), Au(OAcF)(CH2CH2OCH2CF3)(tpy) (3) is formed as the major product. Both 2 and 3 have been characterized by X-ray crystallography. In TFA/TFE mixtures, 2 and 3 are in equilibrium with a slight thermodynamic preference for 2 over 3. Exposure of 2 to ethylene-d4 in TFA caused exchange of ethylene-d4 for ethylene at room temperature. The reaction of 1 with cis-1,2-dideuterioethylene furnished Au(OAcF)(threo-CHDCHDOAcF)(tpy), consistent with an overall anti addition to ethylene. DFT(PBE0-D3) calculations indicate that the first step of the formal insertion is an associative substitution of the OAcF trans to N by ethylene. Addition of free –OAcF to coordinated ethylene furnishes 2. While substitution of OAcF by ethylene trans to C has a lower barrier, the kinetic and thermodynamic preference of 2 over the isomer with CH2CH2OAcF trans to C accounts for the selective formation of 2. The DFT calculations suggest that the higher reaction rates observed in TFA and TFE compared with CH2Cl2 arise from stabilization of the –OAcF anion lost during the first reaction step.

• Moltu, Sissel; Sachse, Daniel; Blakstad, Elin Wahl; Strømmen, Kenneth; Nakstad, Britt; Almaas, Astrid; Westerberg, Ane Cecilie; Rønnestad, Arild Erlend; Brække, Kristin; Veierød, Marit Bragelien; Iversen, Per Ole; Rise, Frode; Berg, Jens Petter & Drevon, Christian A (2014). Urinary metabolite profiles in premature infants show early postnatal metabolic adaption and maturation. Nutrients.  ISSN 2072-6643.  6(5), s 1913- 1930 . doi: 10.3390/nu6051913
• Nytoft, Hans Peter; Kildahl-Andersen, Geir; Šolević Knudsen, Tatjana; Stojanović, Ksenija & Rise, Frode (2014). Compound "J" in Late Cretaceous/Tertiary terrigenous oils revisited: Structure elucidation of a rearranged oleanane coeluting on GC with 18β(H)-oleanane. Organic Geochemistry.  ISSN 0146-6380.  77, s 89- 95 . doi: 10.1016/j.orggeochem.2014.09.010
• Selwood, Andrew I.; Wilkins, Alistair Lawrence; Munday, Rex; Gu, Haifeng; Smith, Kirsty F; Rhodes, Lesley L & Rise, Frode (2014). Pinnatoxin H: A new pinnatoxin analogue from a South China Sea Vulcanodinium rugosum isolate. Tetrahedron Letters.  ISSN 0040-4039.  55(40), s 5508- 5510 . doi: 10.1016/j.tetlet.2014.08.056
• Zhang, Bingzhao; Inngjerdingen, Kari Tvete; Zou, Yuanfeng; Rise, Frode; Michaelsen, Terje Einar; Yan, Pei-Sheng & Paulsen, Berit Smestad (2014). Characterisation and immunomodulating activities of exo-polysaccharides from submerged cultivation of Hypsizigus marmoreus. Food Chemistry.  ISSN 0308-8146.  163, s 120- 128 . doi: 10.1016/j.foodchem.2014.04.092
• Zou, Yuanfeng; Chen, Xing-Fu; Malterud, Karl Egil; Rise, Frode; Barsett, Hilde; Inngjerdingen, Kari Tvete; Michaelsen, Terje Einar & Paulsen, Berit Smestad (2014). Structural features and complement fixing activity of polysaccharides from Codonopsis pilosula Nannf. var. modesta L.T.Shen roots. Carbohydrate Polymers.  ISSN 0144-8617.  113, s 420- 429 . doi: 10.1016/j.carbpol.2014.07.036
• Miles, Christopher; Sandvik, Morten; Nonga, Hezron Emmanuel; Rundberget, Thomas; Wilkins, Alistair Lawrence; Rise, Frode & Ballot, Andreas (2013). Identification of microcystins in a Lake Victoria cyanobacterial bloom using LC-MS with thiol derivatization. Toxicon.  ISSN 0041-0101.  70, s 21- 31 . doi: 10.1016/j.toxicon.2013.03.016 Vis sammendrag

  Microcystins are cyclic heptapeptides from cyanobacteria which are responsible for poisonings of livestock and humans. Cyanobacteria also produce a range of peptides and other compounds that can result in complex chromatograms when samples are analysed by LC–MS. Thiol derivatization of the α,β-unsaturated amide present in most microcystins was recently shown to simplify analysis of LC–MS chromatograms of a Microcystis culture, making it easier to identify peaks corresponding to microcystins in complex mixtures. This method was applied to analysis of extracts taken from a natural cyanobacteria bloom in Mwanza Gulf, Lake Victoria, Tanzania, in 2010, revealing the presence of numerous putative microcystin analogues in the sample. Results were verified using LC–MS2, LC–MS/MS with precursor-ion scanning, and LC–HRMS, leading to identification of 8 major and 17 minor microcystins in the sample, including analogues of microcystin-RY, -RL and -RA. Microcystin-YR (2), -RR (3), and -RY (9) were isolated from bloom material from Lake Victoria, and the structure of 9 was confirmed by NMR spectroscopic analysis and NMR spectral comparison with 2 and 3. Confirmation of the structure of MC-RY (9) facilitated detailed analysis of its MS2 spectrum, thereby supporting the structures of related analogues tentatively established on the basis of MS analyses.

• Puddick, Jonathan; Prinsep, M. R.; Wood, Susanna A.; Miles, Christopher Owen; Rise, Frode; Cary, S. Craig; Hamilton, David P. & Wilkins, Alistair Lawrence (2013). Structural characterization of new microcystins containing tryptophan and oxidized tryptophan residues. Marine Drugs.  ISSN 1660-3397.  11(8), s 3025- 3045 . doi: 10.3390/md11083025 Vis sammendrag

  Microcystins are cyclic peptides produced by cyanobacteria, which can be harmful to humans and animals when ingested. Eight of the (more than) 90 microcystin variants presently characterized, contain the amino acid tryptophan. The well-researched oxidation products of tryptophan; kynurenine, oxindolylalanine, and N-formylkynurenine, have been previously identified in intact polypeptides but microcystin congeners containing oxidized tryptophan moieties have not been reported. Liquid chromatography-tandem mass spectrometric analysis of an extract of Microcystis CAWBG11 led to the tentative identification of two new tryptophan-containing microcystins (MC WAba and MC-WL), as well as eight other microcystin analogs containing kynurenine, oxindolylalanine and N formylkynurenine (Nfk). Investigation of one of these congeners (MC NfkA) by nuclear magnetic resonance spectroscopy was used to verify the presence of Nfk in the microcystin. Liquid chromatography-mass spectrometry analysis of a tryptophan oxidation experiment demonstrated that tryptophan-containing microcystins could be converted into oxidized tryptophan analogs and that low levels of oxidized tryptophan congeners were present intracellularly in CAWBG11. MC-NfkR and MC-LNfk were detected in standards of MC-WR and MC-LW, indicating that care during storage of tryptophan-containing microcystins is required.

• Miles, Christopher; Sandvik, Morten; Nonga, Hezron Emmanuel; Rundberget, Thomas; Wilkins, Alistair Lawrence; Rise, Frode & Ballot, Andreas (2012). Thiol Derivatization for LC-MS Identification of Microcystins in Complex Matrices. Environmental Science and Technology.  ISSN 0013-936X.  46(16), s 8937- 8944 . doi: 10.1021/es301808h Vis sammendrag

  Microcystins are a group of cyclic heptapeptides originating from cyanobacteria. Cyanobacteria also produce a range of peptides and other compounds that can result in complex chromatograms when samples are analyzed by LC-MS. Derivatization with appropriate thiols (e.g., mercaptoethanol) of the olefin in the α,β-unsaturated amide present in most microcystins was shown to simplify analysis of LC-MS chromatograms of sample extracts, making it much easier to identify peaks corresponding to candidate microcystins. Furthermore, interpretation of MS2 spectra was facilitated by addition of the mass associated with the thiol to the α,β-unsaturated amide of microcystins. Cyanotoxins containing Mdha or Dha reacted readily with thiols, whereas Mser, Ser, Mdhb, and thiol-derivatives of Mdha or Dha did not react under the conditions used. This approach therefore provides a convenient LC-MS method to obtain evidence for the presence of Mdha or Dha and can likely be used to differentiate between the isobaric amino acids Mdha and Dhb in candidate cyanotoxin peaks. When O-(2-mercaptoethyl)-O′-methyl-hexa(ethylene glycol) (MEMHEG) (Mwt. 356) was used as the thiol, the resulting derivatives eluted in an LC-MS mass window that was largely free of interferences. This approach simplifies detection of candidate microcystin analogues even in the presence of complex mixtures of coeluting components. The method was used for qualitative analysis of a Microcystis aeruginosa culture from Lake Naivasha, Kenya, and the results were verified using precursor-ion scanning and high-resolution mass spectrometry.

• Røberg-Larsen, Hanne; Strand, Martin Frank; Grimsmo, Anders; Olsen, Peter Angell; Dembinski, Jennifer; Rise, Frode; Lundanes, Elsa; Greibrokk, Tyge; Krauss, Stefan & Wilson, Steven Ray Haakon (2012). High sensitivity measurements of active oxysterols with automated filtration/filter backflush-solid phase extraction-liquid chromatography-mass spectrometry. Journal of Chromatography A.  ISSN 0021-9673.  1255, s 291- 297 . doi: 10.1016/j.chroma.2012.02.002
• Sachse, Daniel; Sletner, Line; Mørkrid, Kjersti; Jenum, Anne Karen; Birkeland, Kåre I.; Rise, Frode; Piehler, Armin & Berg, Jens Petter (2012). Metabolic Changes in Urine during and after Pregnancy in a Large, Multiethnic Population-Based Cohort Study of Gestational Diabetes. PLOS ONE.  ISSN 1932-6203.  7(12) . doi: 10.1371/journal.pone.0052399 Fulltekst i vitenarkiv. Vis sammendrag

  This study aims to identify novel markers for gestational diabetes (GDM) in the biochemical profile of maternal urine using NMR metabolomics. It also catalogs the general effects of pregnancy and delivery on the urine profile. Urine samples were collected at three time points (visit V1: gestational week 8–20; V2: week 28±2; V3:10–16 weeks post partum) from participants in the STORK Groruddalen program, a prospective, multiethnic cohort study of 823 healthy, pregnant women in Oslo, Norway, and analyzed using 1H-NMR spectroscopy. Metabolites were identified and quantified where possible. PCA, PLS-DA and univariate statistics were applied and found substantial differences between the time points, dominated by a steady increase of urinary lactose concentrations, and an increase during pregnancy and subsequent dramatic reduction of several unidentified NMR signals between 0.5 and 1.1 ppm. Multivariate methods could not reliably identify GDM cases based on the WHO or graded criteria based on IADPSG definitions, indicating that the pattern of urinary metabolites above micromolar concentrations is not influenced strongly and consistently enough by the disease. However, univariate analysis suggests elevated mean citrate concentrations with increasing hyperglycemia. Multivariate classification with respect to ethnic background produced weak but statistically significant models. These results suggest that although NMR-based metabolomics can monitor changes in the urinary excretion profile of pregnant women, it may not be a prudent choice for the study of GDM.

• Uhlig, Silvio; Busman, Mark; Shane, Deborah S; Rønning, Helene; Rise, Frode & Proctor, Robert (2012). Identification of Early Fumonisin Biosynthetic Intermediates by Inactivation of the FUM6 Gene in Fusarium verticillioides. Journal of Agricultural and Food Chemistry.  ISSN 0021-8561.  60(41), s 10293- 10301 . doi: 10.1021/jf302967b
• Wangensteen, Helle; Phan, Thi Thanh; Rise, Frode; Halvorsen, Trine Grønhaug & Malterud, Karl Egil (2012). New labdane diterpenes from Solidago canadensis. Natural Product Research.  ISSN 1478-6419.  26(14), s 1348- 1354 . doi: 10.1080/14786419.2011.565005
• Moldes-Anaya, Angel; Rundberget, Thomas; Uhlig, Silvio; Rise, Frode & Wilkins, Alistair Lawrence (2011). Isolation and structure elucidation of secopenitrem D, an indole alkaloid from Penicillium crustosum Thom. Toxicon.  ISSN 0041-0101.  57(2), s 259- 265 . doi: 10.1016/j.toxicon.2010.11.020 Vis sammendrag

  Chemical investigation of three isolates of Penicillium crustosum Thom cultures, one of which was derived from a recent dog poisoning investigation, has led to the isolation and structure elucidation of secopenitrem D (1). Penitrems A-F and roquefortine C were also present in the isolates analyzed. The structure of 1 was unambiguously assigned based on extensive 1D and 2D-NMR spectroscopic experiments, MS-aided structural studies and by comparison with structurally related congeners. Secopenitrem D lacks the C-16-C-18 ether linkage present in penitrems A-F.

• Selwood, Andrew I.; Miles, Christopher; Wilkins, Alistair Lawrence; van Ginkel, Roel; Munday, Rex; Rise, Frode & McNabb, Paul (2010). Isolation, Structural Determination and Acute Toxicity of Pinnatoxins E, F and G. Journal of Agricultural and Food Chemistry.  ISSN 0021-8561.  58(10), s 6532- 6542 . doi: 10.1021/jf100267a
• Tutturen, Astrid Elisabeth Voorham; Holm, Anders; Jørgensen, Marit; Stadtmüller, Patricia; Rise, Frode & Fleckenstein, Burkhard (2010). A technique for the specific enrichment of citrulline-containing peptides. Analytical Biochemistry.  ISSN 0003-2697.  403(1-2), s 43- 51 . doi: 10.1016/j.ab.2010.04.012
• Wilson, Steven Ray Haakon; Strand, Martin Frank; Krapp, Andreas; Rise, Frode; Herstad, Gunnar; Malterud, Karl Egil & Krauss, Stefan (2010). Hedgehog antagonists cyclopamine and dihydroveratramine can be mistaken for each other in Veratrum album. Journal of Pharmaceutical and Biomedical Analysis.  ISSN 0731-7085.  53(3), s 497- 502 . doi: 10.1016/j.jpba.2010.05.024
• Wilson, Steven Ray Haakon; Strand, Martin Frank; Krapp, Andreas; Rise, Frode; Petersen, Dirk & Krauss, Stefan (2010). Hedgehog antagonist cyclopamine isomerizes to less potent forms when acidified. Journal of Pharmaceutical and Biomedical Analysis.  ISSN 0731-7085.  52(5), s 707- 713 . doi: 10.1016/j.jpba.2010.02.017
• Gundersen, Lise-Lotte; Rise, Frode & Undheim, Kjell (2009). Methylzirconium Tributoxide, In Leo A. Paquette (ed.),  Encyclopedia of Reagents for Organic Synthesis. 2. Ed.  John Wiley & Sons.  ISBN 978-0-470-01754-8.  9.  s 7161 - 7162
• Gundersen, Lise-Lotte; Rise, Frode & Undheim, Kjell (2009). Zirconium(III) Chloride, In Leo A. Paquette (ed.),  Encyclopedia of Reagents for Organic Synthesis. 2. Ed.  John Wiley & Sons.  ISBN 978-0-470-01754-8.  13.  s 10965 - 10965
• Gundersen, Lise-Lotte; Rise, Frode; Undheim, Kjell; Aguilar, E. & Garcia-Garcia, P (2009). Titanium(IV) Chloride, In Leo A. Paquette (ed.),  Encyclopedia of Reagents for Organic Synthesis. 2. Ed.  John Wiley & Sons.  ISBN 978-0-470-01754-8.  12.  s 9526 - 9552
• Gundersen, Lise-Lotte; Rise, Frode; Undheim, Kjell & Mendez-Andino, J. (2009). Titanium(III) Chloride, In Leo A. Paquette (ed.),  Encyclopedia of Reagents for Organic Synthesis. 2. Ed.  John Wiley & Sons.  ISBN 978-0-470-01754-8.  12.  s 9523 - 9526
• Huhn, J; Jeffrey, PD; Larsen, Kristofer; Rundberget, T; Rise, Frode; Cox, NR; Arcus, V; Shi, YG & Miles, CO (2009). A Structural Basis for the Reduced Toxicity of Dinophysistoxin-2. Chemical Research in Toxicology.  ISSN 0893-228X.  22(11), s 1782- 1786 . doi: 10.1021/tx9001622
• Togola, Adiaratou; Hedding, Berte; Theis, Annette; Wangensteen, Helle; Rise, Frode; Paulsen, Berit Smestad; Diallo, Drissa & Malterud, Karl Egil (2009). 15-Lipoxygenase Inhibitory Effects of Prenylated Flavonoids from Erythrina senegalensis. Planta Medica.  ISSN 0032-0943.  75(10), s 1168- 1170 . doi: 10.1055/s-0029-1185449
• Gorbitz, Carl Henrik & Rise, Frode (2008). Template-directed supramolecular assembly of a new type of nanoporous peptide-based material. Journal of Peptide Science.  ISSN 1075-2617.  14(2), s 210- 216 . doi: 10.1002/psc.985 Vis sammendrag

  Dipeptides with two hydrophobic residues are known to often form crystals with hydrophobic or hydrophilic channels. One of the exceptions is Leu-Ile, which has been previously shown to crystallize as a nonporous 0.75 hydrate in the hexagonal space group P61 with Z = 4. We have now found that in the presence of D-Leu, a second pseudopolymorph of the dipeptide is formed. The crystal structure has hydrophilic, water-filled channels with an irregular cross section of approximately 5.5 × 3.5 Å and constitutes the first example of a crystal packing arrangement where the direction of the channels is perpendicular to the direction of hydrophobic stacking of side chains rather than parallel as in all other porous peptide-based materials.

• Larsen, Kristofer; Petersen, Dirk; Wilkins, Alistair L.; Samdal, Ingunn; Sandvik, Morten; Rundberget, Thomas; Goldstone, David; Arcus, Vickery; Hovgaard, Peter; Rise, Frode; Rehmann, N.; Hess, P. & Miles, Christopher O. (2007). Clarification of the C-35 Stereochemistries of Dinophysistoxin-1 and Dinophysistoxin-2 and Its Consequences for Binding to Protein Phosphatase. Chemical Research in Toxicology.  ISSN 0893-228X.  20(6), s 868- 875 . doi: 10.1021/tx700016m Vis sammendrag

  Okadaic acid analogues are well known as protein phosphatase inhibitors and occur naturally in marine shellfish feeding on dinoflagellates of the genus Dinophysis, leading to diarrhetic shellfish poisoning of shellfish consumers. Knowledge of the correct structures for these toxins is important in understanding their toxicology, biochemistry, and biosynthesis. We have performed extensive NMR analyses on okadaic acid (1), dinophysistoxin-1 (DTX-1), and dinophysistoxin-2 (DTX-2) obtained from natural sources. Consequently, we were able to unambiguously deduce the stereochemistries at C-35 for DTX-1 and DTX-2 based on analysis of NMR coupling constants and NOE interactions. Our results revealed that DTX-2 (3) has a stereochemistry opposite to that of DTX-1 (2) at C-35. Molecular modeling of the docking of 1-3 with protein phosphatase-1 and protein phosphatase 2A (PP2A) suggested that the reduced affinity of DTX-2 for PP2A may be due to the newly defined stereochemistry at the 35-methyl group. The implications of these findings for biosynthesis and toxicology are discussed.

• Larsen, Kristofer; Petersen, Dirk; Wilkins, Alistair; Samdal, Ingunn; Sandvik, Morten; Rundberget, Thomas; Goldstone, David; Arcus, Vickery; Hovgaard, Peter; Rise, Frode; Rehmann, Nils; Hess, Philipp & Miles, Christopher (2007). Clarification of the C-35 stereochemistries of dinophysistoxin-1 and dinophysistoxin-2 and its consequences for binding to protein phosphatase. Chemical Research in Toxicology.  ISSN 0893-228X.  20, s 868- 875 Vis sammendrag

  Okadaic acid analogues are well known as protein phosphatase inhibitors and occur naturally in marine shellfish feeding on dinoflagellates of the genus Dinophysis, leading to diarrhetic shellfish poisoning of shellfish consumers. Knowledge of the correct structures for these toxins is important in understanding their toxicology, biochemistry, and biosynthesis. We have performed extensive NMR analyses on okadaic acid (1), dinophysistoxin-1 (DTX-1), and dinophysistoxin-2 (DTX-2) obtained from natural sources. Consequently, we were able to unambiguously deduce the stereochemistries at C-35 for DTX-1 and DTX-2 based on analysis of NMR coupling constants and NOE interactions. Our results revealed that DTX-2 (3) has a stereochemistry opposite to that of DTX-1 (2) at C-35. Molecular modeling of the docking of 1-3 with protein phosphatase-1 and protein phosphatase 2A (PP2A) suggested that the reduced affinity of DTX-2 for PP2A may be due to the newly defined stereochemistry at the 35-methyl group. The implications of these findings for biosynthesis and toxicology are discussed.

• Rundberget, Thomas; Sandvik, Morten; Larsen, Kristofer; Pizarro, G.M.; Reguera, Beatriz; Castberg, T; Gustad, E; Loader, J.I.; Rise, Frode; Wilkins, Alistair L. & Miles, Christopher O. (2007). Extraction of microalgal toxins by large-scale pumping of seawater in Spain and Norway, and isolation of okadaic acid and dinophysistoxin-2. Toxicon.  ISSN 0041-0101.  50(7), s 960- 970 . doi: 10.1016/j.toxicon.2007.07.003 Vis sammendrag

  Marine biotoxins from microalgae can accumulate in shellfish and lead to poisoning of human consumers as well as fish, marine mammals and sea birds. Toxicological assessment of the toxins and development of analytical methods require large amounts of high-purity toxins and their metabolites. Although these toxins can be obtained in limited amounts from contaminated shellfish or from microalgal cultures, difficulties arise when the toxin-producing microalga is difficult to culture or its identity is not known. To circumvent this problem, we have developed a large-scale method for solid-phase extraction (SPE) of lipophilic biotoxins from natural microalgal blooms in seawater. To enhance subsequent purification of toxins adsorbed on the column, we included a filtration step to release the toxins from the cells while removing insoluble compounds and cellular debris. The efficacy of the method was illustrated by extraction and purification of okadaic acid and dinophysistoxin-2 from a high-density Dinophysis acuta bloom in Spain and from a mixed bloom containing low densities of D. acuta in Norway. Isolation of the toxins adsorbed on the SPE column was simple and efficient, and results obtained so far indicate that the method is potentially applicable to a wide range of microalgal toxins such as azaspiracids, pectenotoxins, spirolides and microcystins. The method should also be useful for harvesting toxins from large-scale microalgal cultures, and for bioprospecting for and isolation of bioactive natural products from marine and freshwater environments.

• Aarnes, Halvor; Eriksen, Aud Else Berglen; Petersen, Dirk & Rise, Frode (2007). Accumulation of ammonium in Norway spruce (Picea abies) seedlings measured by in vivo 14N-NMR. Journal of Experimental Botany.  ISSN 0022-0957.  58(5), s 929- 934 . doi: 10.1093/jxb/erl247 Vis sammendrag

  http://jxb.oxfordjournals.org/cgi/content/abstract/erl247? ijkey=y8vx24OpXL2qpyu&keytype=ref 14N-NMR and 31P-NMR have been used to monitor the in vivo pH in roots, stems, and needles from seedlings of Norway spruce, a typical ammonium-tolerant plant. The vacuolar and cytoplasmic pH measured by 31P-NMR was found to be c. pH 4.8 and 7.0, respectively, with no significant difference between plants growing with ammonium or nitrate as the N-source. The 1H-coupled 14NH resonance is pH-sensitive: at alkaline pH it is a narrow singlet line and below pH 4 it is an increasing multiplet line with five signals. The pH values in ammonium-containing compartments measured by 14N-NMR ranged from 3.7 to 3.9, notably lower than the estimated pH values of the Pi pools. This suggests that, in seedlings of Norway spruce, ammonium is stored in vacuoles with low pH possibly to protect the seedlings against the toxic effects of ammonium (NH) or ammonia (NH3). It was also found that concentrations of malate were 3–6 times higher in stems than in roots and needles, with nitrate-grown plants containing more malate than plants grown with ammonium. Key words: Ammonium, cytoplasmic pH, in vivo 14N-NMR, in vivo 31P-NMR, malate, organic acids, Picea abies (L.) Karst, vacuolar pH

• Gundersen, LL; Charnock, Colin; Negussie, AH; Rise, F; Teklu, S & Weldegirma, Solomon Teklu (2007). Synthesis of indolizine derivatives with selective antibacterial activity against Mycobacterium tuberculosis. European Journal of Pharmaceutical Sciences.  ISSN 0928-0987.  30 . doi: 10.1016/j.ejps.2006.09.006
• Mmatli, Edward M; Malerød, Helle; Wilson, Steven Ray Haakon; Abegaz, Berhanu m; Greibrokk, Tyge; Lundanes, Elsa; Malterud, Karl Egil; Petersen, Dirk & Rise, Frode (2007). Identification of major metal complexing compounds in Blepharis aspera. Analytica Chimica Acta.  ISSN 0003-2670.  597(1), s 24- 31 . doi: 10.1016/j.aca.2007.06.042 Vis sammendrag

  Verbascoside and isoverbascoside, present at 0.7% and 0.2% (w/w dryweight), were identified to be major compounds that could contribute to the metal complexation in Blepharis aspera collected in Botswana, Africa. The metallophyte B. aspera has high ability to cope with a high level of metal accumulation. The presence of metal complexing compounds and/or antioxidants can prevent oxidative reactions in lipids, proteins and DNA that take place due to the metal accumulation. On-line liquid chromatography–solid phase extraction–nuclear magnetic resonance (LC–SPE–NMR) was applied for the identification, while electrospray-mass spectrometry (ESI-MS) and UV-vis spectroscopy was used to assess whether these compounds can complex with metals. It was found that verbascoside and isoverbascoside may form complexes with nickel, iron (verbascoside only) and copper. Thus, the presence of verbascoside and isoverbascoside can explain the survival of B. aspera in mineral-rich areas.

• Nguyen, Nga H. T.; Morland, C; Gonzales, Susana Villa; Rise, Frode; Storm-Mathisen, Jon; Gundersen, Vidar & Hassel, Bjornar (2007). Propionate increases neuronal histone acetylation, but is metabolized oxidatively by glia. Relevance for propionic acidemia. Journal of Neurochemistry.  ISSN 0022-3042.  101(3), s 806- 814 . doi: PMID:17286595 Vis sammendrag

  In propionic acidemia, propionate acts as a metabolic toxin in liver cells by accumulating in mitochondria as propionyl-CoA and its derivative, methylcitrate, two tricarboxylic acid cycle inhibitors. Little is known about the cerebral metabolism of propionate, although clinical effects of propionic acidemia are largely neurological. We found that propionate was metabolized oxidatively by glia: [3-(14)C]propionate injected into mouse striatum or cortex, gave a specific activity of glutamine that was 5-6 times that of glutamate, indicating metabolism in cells that express glutamine synthetase, i.e., glia. Further, cultured cerebellar astrocytes metabolized [3-(14)C]propionate; cultured neurons did not. However, both cultured cerebellar neurons and astrocytes took up [(3)H]propionate, and propionate exposure increased histone acetylation in cultured neurons and astrocytes as well as in hippocampal CA3 pyramidal neurons of wake mice. The inability of neurons to metabolize propionate may be due to lack of mitochondrial propionyl-CoA synthetase activity or transport of propionyl residues into mitochondria, as cultured neurons expressed propionyl-CoA carboxylase, a mitochondrial matrix enzyme, and oxidized isoleucine, which becomes converted into propionyl-CoA intramitochondrially. The glial metabolism of propionate suggests astrocytic vulnerability in propionic acidemia when intramitochondrial propionyl-CoA may accumulate. Propionic acidemia may alter both neuronal and glial gene expression by affecting histone acetylation.

• Nguyen, Nga Tran Huynh; Gonzalez, Susan Villa; Rise, Frode & Hassel, Bjørnar (2007). Cerebral metabolism of glucose and pyruvate in soman poisoning - A C-13 nuclear magnetic resonance spectroscopic study. Neurotoxicology.  ISSN 0161-813X.  28(1), s 13- 18 . doi: PMID:17087995 Vis sammendrag

  Organophosphates, such as the nerve gas soman, cause inhibition of acetylcholine esterase, accumulation of acetylcholine in synaptic clefts, and excessive activation of cholinergic receptors, causing central nervous symptoms such as tremor and seizures. Soman-poisoned animals have low brain levels of ATP, indicating that energy demand is greater than energy supply. We investigated whether soman poisoning is accompanied by an increased brain metab. of glucose, as can be inferred from the accumulation of radiolabeled 2-deoxyglucose found in previous studies, or whether soman poisoning entails impairment of cerebral energy metab. We performed 13C NMR spectroscopy on brain exts. from soman-poisoned mice (160 mg/kg; 1 LD50) that had been dosed with 13C-labeled glucose or pyruvate i.v. Formation of 13C-labeled glutamate, GABA and glutamine from [1-13C]glucose was reduced by approx. 30% in awake, soman-intoxicated animals, but formation of these amino acids from [3-13C]pyruvate was not different in soman-intoxicated animals and controls. These results suggest that soman intoxication entails inhibition of glycolysis, but not of tricarboxylic acid cycle activity in the brain. However, when brain metab. was depressed by a sedative dose of diazepam (5 mg/kg) soman intoxication caused increased metab. of 13C-labeled glucose. The latter finding shows that the soman-poisoned brain has a high energy requirement even during anticonvulsant therapy. We conclude that metabolic inhibition, as seen in awake, soman-intoxicated animals, may lower seizure threshold and contribute to soman-related neurodegeneration and lethality.

• Utenova, Bibigul; Malterud, Karl Egil & Rise, Frode (2007). Antioxidant activity of O-protected derivatives of (-)-epigallocatechin-3-gallate: inhibition of soybean and rabbit 15-lipoxygenases. ARKIVOC.  ISSN 1551-7004.  ix, s 6- 16 Vis sammendrag

  (-)-Epigallocatechin-3-gallate (EGCG) was protected at all eight phenolic groups as the methyl ether or acetate, propionate or butyrate esters. The synthetic derivatives were examined for antioxidant activities. The compounds were tested as potential diphenylpicrylhydrazyl (DPPH) radical scavengers and as inhibitors of 15-lipoxygenase (15-LO) enzymes from soybeans and rabbit reticulocytes. The O-protected EGCG derivatives were essentially inactive as DPPH scavengers but showed profound inhibiting effects on both types of 15-LO, and the inhibitory effects towards the two enzymes were significantly correlated. The O-protected EGCG derivatives inhibited 15-LO more strongly that EGCG itself. EGCG and its O-protected derivatives were also screened for antibacterial activity against M. tuberculosis. Keywords: Flavonoids, (-)-Epigallocatechin-3-gallate, 15-Lipoxygenase, Radical scavenging Introduction

• Wilson, Steven Ray Haakon; Greibrokk, Tyge; Lundanes, Elsa; Malerød, Helle; Petersen, Dirk & Rise, Frode (2007). An alternative LC-SPE-NMR design. Journal of Separation Science.  ISSN 1615-9306.
• Wilson, Steven Ray Haakon; Malerød, Helle; Petersen, Dirk; Rise, Frode; Lundanes, Elsa & Greibrokk, Tyge (2007). An alternative multiple-trapping LC-SPE-NMR system. Journal of Separation Science.  ISSN 1615-9306.  30, s 322- 328 . doi: 10.1002/jssc.200600238
• Holm, Anders; Rise, Frode; Sessler, Nicole; Sollid, Ludvig Magne; Undheim, Kjell & Fleckenstein, Burkhard (2006). Specific modification of peptiode-bound citrulline residues. Analytical Biochemistry.  ISSN 0003-2697.  352(1), s 68- 76
• Miles, Christopher O.; Wilkins, Alistair L.; Hawkes, Alan D.; Jensen, Dwayne J.; Coony, Janine M.; Larsen, Kristofer; Petersen, Dirk; Beuzenberg, Veronica; MacKenzie, A. Lincoln & Rise, Frode (2006). Isolation and identification of a cis-C8-diol-ester of okadaic acid from Dinophysis acuta in New Zealand. Toxicon.  ISSN 0041-0101.  48(2), s 195- 203
• Wilkins, Alistair L.; Rehman, Nils; Miles, Christopher O.; Torgersen, Trine; Rundberget, Thomas; Keogh, Myra; Petersen, Dirk; Hess, Philip & Rise, Frode (2006). Identification of Fatty Acid Esters of Pectenotoxin-2 Seco Acid in Blue Mussels (Mytilus edulis) from Ireland. Journal of Agricultural and Food Chemistry.  ISSN 0021-8561.  54(15), s 5672- 5678
• Malerød, Helle; Petersen, Dirk; Nebojsa, Simic; Bobu, Maria-Magdalena; Rise, Frode; Lundanes, Elsa; Greibrokk, Tyge & Wilson, Steven Ray Haakon (2006). Controlling LC-SPE-NMR systems. Journal of Separation Science.  ISSN 1615-9306.  29(4), s 582- 589
• Spilsberg, Bjorn; Rise, Frode; Petersen, Dirk & Nissen-Meyer, Jon (2006). Thymidine secretion by hybridoma and myeloma cells. Biochemical and Biophysical Research Communications - BBRC.  ISSN 0006-291X.  342, s 221- 226
• Wilson, Steven Ray; Malerød, Helle; Petersen, Dirk; Simic, Nebojsa; Bobu, Maria-Magdalena; Rise, Frode; Lundanes, Elsa & Greibrokk, Tyge (2006). Controlling LC-SPE-NMR Systems. Journal of Separation Science.  ISSN 1615-9306.  29(4), s 582- 589
• Bråthe, Anders; Gundersen, Lise-Lotte; Rise, Frode & Eriksen, Aud Else Berglen (2005). 6-Cyclopropylpurines as Novel Potent Analogs of Cytokinins. Journal of Plant Growth Regulation.  ISSN 0721-7595.  24, s 41- 45
• Rise, Frode; Miles, Christopher O.; Samdal, Ingunn; Aasen, John A. G.; Jensen, Dwayne J.; Quilliam, Michael A.; Briggs, Lyn M.; Wilkins, Alistair L.; Cooney, Janine M.; MacKenzie, A. Lincoln & Petersen, Dirk (2005). Evidence for numerous analogs of yessetoxin in Protoceratium reticulatum. Harmful Algae.  ISSN 1568-9883.  4, s 1075- 1091 . doi: 10.1016/j.hal.2005.03.005
• Bråthe, Anders; Gundersen, Lise-Lotte; Malterud, Karl Egil & Rise, Frode (2005). 6-Substituted purines as inhibitors of 15-lipoxygenase; a structure-activity study. Archiv der Pharmazie.  ISSN 0365-6233.  338, s 159- 166 . doi: 10.1002/ardp.200400951
• Miles, Christopher; Samdal, Ingunn; Bunæs, John A Aasen; Jensen, Dwayne; Quilliam, Michael; Petersen, Dirk; Briggs, Lyn; Wilkins, Alistair; Rise, Frode; Cooney, Janine & MacKenzie, A. Lincoln (2005). Evidence for numerous analogs of yessotoxin in Protoceratium reticulatum. Harmful Algae.  ISSN 1568-9883.  4(6), s 1075- 1091
• Rise, Frode; Gonzales, Susana Villa; Hassel, Bjørnar & Nguyen, Nga H. T. (2005). Brain metabolism of exogenous pyruvate. Journal of Neurochemistry.  ISSN 0022-3042.  95(1), s 284- 293
• Teklu, Solomon; Gundersen, Lise-Lotte; Larsen, Tove; Malterud, Karl Egil & Rise, Frode (2005). Indolizine 1-sulfonates as potent inhibitors of 15-lipoxygenase from soybeans. Bioorganic & Medicinal Chemistry.  ISSN 0968-0896.  13, s 3127- 3139
• Teklu, Solomon; Gundersen, Lise-Lotte; Rise, Frode & Tilset, Mats (2005). Electrochemical Studies of Biologically Active Indolizines. Tetrahedron.  ISSN 0040-4020.  65, s 4643- 4656
• Abegaz, Berhanu m; Ngadjui, Bonaventure t; Folefoc, Gabriel n; Fotso, Serge; Ambassa, Pantaleon; Bezabih, Merhatibeb; Dongo, Etienne; Rise, Frode & Petersen, Dirk (2004). Prenylated flavonoids, monoterpenoid furanocoumarins and other constituents from the twigs of Dorstenia elliptica (Moraceae). Phytochemistry.  ISSN 0031-9422.  65, s 221- 226
• Bråthe, Anders; Gundersen, Lise-Lotte; Nissen-Meyer, Jon; Rise, Frode & Spilsberg, Bjørn (2003). Cytotoxic activity of 6-alkanyl- and 6-alkenylpurines. Bioorganic & Medicinal Chemistry Letters.  ISSN 0960-894X.  13, s 877- 880
• Gundersen, Lise-Lotte; Malterud, Karl Egil; Negusie, Ayele H.; Rise, Frode; Teklu, Solomon & Østby, Ole Benny (2003). Indolizines as Novel Potent Inhibitors of 15-Lipoxygenase. Bioorganic & Medicinal Chemistry.  ISSN 0968-0896.  11, s 5409- 5415
• Gundersen, Lise-Lotte; Negusie, Ayele H.; Rise, Frode & Østby, Ole Benny (2003). Antimycobacterial activity of 1-substituted indolizines. Archiv der Pharmazie.  ISSN 0365-6233.  336, s 191- 195
• Andresen, Geir; Gundersen, Lise-Lotte; Nissen-Meyer, Jon; Rise, Frode & Spilsberg, Bjørn (2002). Cytotoxic and Antibacterial Activity of 2-Oxopurine Derivatives. Bioorganic & Medicinal Chemistry Letters.  ISSN 0960-894X.  12, s 567- 569
• Bråthe, Anders; Andresen, Geir; Gundersen, Lise-Lotte; Malterud, Karl Egil & Rise, Frode (2002). Antioxidant activity of synthetic cytokinin analogues: 6-Alkynyl- and 6-alkenylpurines as novel 15-lipoxygenase inhibitors. Bioorganic & Medicinal Chemistry.  ISSN 0968-0896.  10, s 1581- 1586
• Aabel, Siri; Fossheim, Sigrid Lise & Rise, Frode (2001). "Nuclear magnetic resonance (NMR) studies of homeopathic solutions.". British Homeophatic Journal.  90, s 14- 20 Vis sammendrag

  http://folk.uio.no/froderi/Aabel.pdf

• Andresen, Geir; Eriksen, Aud Else Berglen; Dalhus, Bjørn; Gundersen, Lise-Lotte & Rise, Frode (2001). Synthesis of 6-substituted purin-2-ones with potential cytokinin activity. Journal of the Chemical Society. Perkin transactions 1.  ISSN 0300-922X.  s 1662- 1672 Vis sammendrag

  http://folk.uio.no/froderi/GeirAndresen3.pdf

• Rise, Frode; Andresen, Geir & Gundersen, Lise-Lotte (2001). Synthesis of 2-oxopurine adducts with structural resemblance to Efavirenz and DPC 961 as potential NNRT-inhibitors. Arkivoc. Free Online Journal of Organic Chemistry.  Volume 2001(x), s 35- 45 Vis sammendrag

  http://www.arkat-usa.org/ark/journal/Volume2/Part3/Undheim/KU-247A/247.htm Abstract 6-Cyclopropylethynyl-6-trifluoromethyl dihydro-2-oxopurines have been prepared with completely regioselective addition of trimethyl(trifluoromethyl)silane and cyclopropylethynylmagnesium bromide to 1,9-dialkylated 2-oxopurines as key-steps. The target compounds are structurally related to the Non-Nucleoside reverse transcriptase inhibitors Efavirenz and DPC 961

• Rise, Frode; Singh, Pushap G.; Klaveness, Jo & Aasen, Arne Jørgen (2001). Lipophilic X-Ray Contrast Agents. Diatrizoyl Double Esters with Cholesterol and Cholic Acid. Arkivoc. Free Online Journal of Organic Chemistry.  Volume 2001(x), s 7- 15 Vis sammendrag

  http://www.arkat-usa.org/ark/journal/Volume2/Part3/Undheim/KU-205A/205.htm Abstract Potential biodegradable and organ-specific X-ray contrast agents have been prepared by linking diatrizoic acid to cholesterol and cholic acid, respectively, via a spacer group containing a carbonate double ester. In vitro experiments revealed that the cholic acid esters were enzymatically degraded in the presence of pig liver esterase, while the double esters with cholesterol appeared to be stable, possibly due to low solubility in water.

• Sing, P. G.; Klaveness, Jo; Rise, Frode & Aasen, Arne Jørgen (2001). Lipophilic X-Ray Contrast Agents Diatrizoyl Double Esters with Cholesterol and Cholic Acid. Archive for Organic Chemistry (Arkivoc).  2(8) Vis sammendrag

  Potential biodegradable and organ-specific X-ray contrast agents have been prepared by linking diatrizoic acid to cholesterol and cholic acid, respectively, via a spacer group containing a carbonate double ester. In vitro experiments revealed that the cholic acid esters were enzymatically degraded in the presence of pig liver esterase, while the double esters with cholesterol appeared to be stable, possibly due to low solubility in water.

• Østby, Ole Benny; Gundersen, Lise-Lotte; Rise, Frode; Antonsen, Øyvind Gunnar; Fosnes, K.; Larsen, V.; Bast, Aalt; Custers, Ilse & Haenen, Guido R. M. M. (2001). Synthesis of 1-Substituted 7-Cyano-2,3-diphenylindolizines and Evaluation of Antioxidant Properties. Arch. Pharm. Pharm. Med. Chem..  334, s 21- 24
• Netland, Kjetil Andreas; Gundersen, Lise-Lotte & Rise, Frode (2000). An Improved Synthesis of Dialkylcyclopropenones. Synthetic Communications.  ISSN 0039-7911.  30, s 1767- 1777
• Spilsberg, Bjørn; Rise, Frode; Petersen, Dirk & Nissen-Meyer, Jon (2000). Secretion of thymidine by hybridoma cells, In Esther Zoref-Shani & Oded Sperling (ed.),  Advances in experimental medicine and biology: Purine and pyrimidine metabolism in man.  Kluwer Academic / Plenum Publishers, New York.  ISBN 0-306-46515-9.  s 295 - 301
• Østby, Ole Benny; Dalhus, Bjørn; Gundersen, Lise-Lotte; Rise, Frode; Bast, Aalt & Haenen, Guido R. M. M. (2000). Synthesis of 1-Substituted 7-Cyano-2,3-diphenylindolizines and Evaluation of Antioxidant Properties. European Journal of Organic Chemistry.  ISSN 1434-193X.  9(22), s 3763- 3770
• Bråthe, Anders; Gundersen, Lise-Lotte; Rise, Frode; Eriksen, Aud Else Berglen; Vollsnes, Ane & Wang, Linnea (1999). Synthesis of 6-Alkenyl- and 6-Alkynylpurines with Cytokinin Activity. Tetrahedron.  ISSN 0040-4020.  55, s 211- 288
• Islam, Gulshan Ara; Greibrokk, Tyge; Rise, Frode & Øvrebø, Steinar (1999). Epimerization of benzo(a)pyrene-tetrols after acid hydrolysis, implications for determination of benzo(a)pyrene adducts in protein and DNA. Mutation research.  ISSN 0027-5107.  423, s 47- 54 Vis sammendrag

  http://www.uio.no/~froderi/Gulshan.pdf

• Liu, Fusheng; Dalhus, Bjørn; Gundersen, Lise-Lotte & Rise, Frode (1999). Nucleophilic Addition and Cycloaddition on 2- and 8-Vinylpurines. Acta Chemica Scandinavica.  ISSN 0904-213X.  53, s 269- 279 Vis sammendrag

  http://folk.uio.no/froderi/Liu.pdf

• Nolsøe, Jens M. J.; Gundersen, Lise-Lotte & Rise, Frode (1999). Regiochemistry in Pd-Mediated Coupling between 6,8-Dihalopurines and Organometallic Reagents. Acta Chemica Scandinavica.  ISSN 0904-213X.  53, s 366- 372 Vis sammendrag

  http://folk.uio.no/froderi/Jens2.pdf

• Borgen, Gerd; Dale, Johannes; Gundersen, Lise-Lotte; Rise, Frode; Krivokapic, Alexander & Øverås, Anniken Thomsen (1998). Conformations of 11- and 14-membered Ring Monolactams. Acta Chemica Scandinavica.  ISSN 0904-213X.  52, s 1110- 1115 Vis sammendrag

  http://www.uio.no/~froderi/publications.html

• Nasir, Achmad I.; Gundersen, Lise-Lotte; Rise, Frode; Antonsen, Øyvind; Kristensen, Tom Arne; Langhelle, B.; Bast, Aalt; Custers, Ilse; Haenen, Guido R. M. M. & Wikstrøm, Håkan (1998). Inhibition of Lipid Peroxidation mediated by Indolizines. Bioorganic & Medicinal Chemistry Letters.  ISSN 0960-894X.  s 1828- 1832 Vis sammendrag

  http://folk.uio.no/froderi/Indolizin.pdf

• Nasir, Ahmad Izuddin; Gundersen, Lise-Lotte; Rise, Frode; Antonsen, Øyvind; Kristensen, Trond; Langhelle, Bjarte; Bast, Aalt; Custers, Ilse; Haenen, Guido R. M. M. & Wikstrøm, Håkan (1998). Inhibition of Lipid Peroxidation mediated by Indolizines. Bioorganic & Medicinal Chemistry Letters.  ISSN 0960-894X.  8(14), s 1829- 1832 Vis sammendrag

  Esters, ethers, carbonates and carbamates of 1-indolizinols and azain dolizinols exhibit a profound inhibition of lipid peroxidation in vit ro. The antioxidants were prepared by cyclization of pyridines and di azines with diphenylcyclopropenone followed by introduction of the O- substituent.

• Nolsøe, Jens M. J.; Gundersen, Lise-Lotte & Rise, Frode (1998). Synthesis of 8-Halopurines by Reaction of Lithiated Purines with Appropriate Halogen Donors. Synthetic Communications.  ISSN 0039-7911.  28(23), s 4303- 4315 Vis sammendrag

  http://folk.uio.no/froderi/publications.html

• Øverås, Anniken Thomsen; Gundersen, Lise-Lotte & Rise, Frode (1997). Lewis Acid Mediated Diels-Alder Reactions of 6-Vinylpurines. Tetrahedron.  ISSN 0040-4020.  53, s 1777- 1786 Vis sammendrag

  http://www.uio.no/~froderi/Anniken1.pdf

• Øverås, Anniken Thomsen; Rise, Frode; Gundersen, Lise-Lotte & Bakkestuen, Anne Kristin Vibstad (1997). Addition of Nucleophiles to 6-Vinylpurines. Acta Chemica Scandinavica.  ISSN 0904-213X.  51, s 1116- 1124 Vis sammendrag

  http://www.uio.no/~froderi/Anniken2.pdf

• Andresen, Geir; Gundersen, Lise-Lotte & Rise, Frode (1996). Regiochemistry in Addition of Grignard Reagents to N,N-Dibenzylated 2-Purinones. Tetrahedron.  ISSN 0040-4020.  52, s 12979- 12992 Vis sammendrag

  http://folk.uio.no/froderi/publications.html

• Borgen, Gerd; Dale, Johannes; Rise, Frode & Gundersen, Lise-Lotte (1996). Conformations and Conformational Processes of Undecylolactam. Magnetic Resonance in Chemistry.  ISSN 0749-1581.  34, s 289- 292 Vis sammendrag

  http://folk.uio.no/froderi/publications.html

• Hammer, Kristin; Hatlelid, Jostein; Grøtli, Morten; Arukwe, J.; Rise, Frode; Klaveness, Jo & Undheim, Kjell (1996). Ether, Carbonate and Urethane Deoxynucleoside Derivatives as Prodrugs. Acta Chemica Scandinavica.  ISSN 0904-213X.  50, s 609- 622
• Langli, Geir; Gundersen, Lise-Lotte & Rise, Frode (1996). Regiochemistry in Stille Couplings of 2,6-Dihalopurines. Tetrahedron.  ISSN 0040-4020.  52, s 5625- 5638 Vis sammendrag

  http://folk.uio.no/froderi/publications.html

• Andresen, Geir; Gundersen, Lise-Lotte; Lundmark, Max; Sundell, Staffan & Rise, Frode (1995). Regioselective Addition of Grignard Reagents to a 2-Oxopurinium Salt. Tetrahedron.  ISSN 0040-4020.  51, s 3655- 3664 Vis sammendrag

  http://folk.uio.no/froderi/GeirAndresen1.pdf

• Borgen, Gerd; Dale, Johannes; Gundersen, Lise-Lotte & Rise, Frode (1995). Conformations and Conformational Interconversions of Pelargolactam. Magnetic Resonance in Chemistry.  ISSN 0749-1581.  33, s 252- 255
• Gundersen, Lise-Lotte; Langli, Geir & Rise, Frode (1995). Regioselective Pd-Mediated Coupling between 2,6-Dichloropurines and Organometallic reagents. Tetrahedron Letters.  ISSN 0040-4039.  36, s 1945- 1948
• Gundersen, Lise-Lotte; Rise, Frode & Undheim, Kjell (1995). Methylzirconium Tributoxide, In Leo A. Paquette (ed.),  Encyclopedia of Reagents for Organic Synthesis.  John Wiley & Sons.  ISBN 0-471-93623-5.  8.  s 3645 - 3646
• Gundersen, Lise-Lotte; Rise, Frode & Undheim, Kjell (1995). Titanium(III) Chloride, In Leo A. Paquette (ed.),  Encyclopedia of Reagents for Organic Synthesis.  John Wiley & Sons.  ISBN 0-471-93623-5.  7.  s 4911 - 4913
• Gundersen, Lise-Lotte; Rise, Frode & Undheim, Kjell (1995). Titanium(IV) Chloride, In Leo A. Paquette (ed.),  Encyclopedia of Reagents for Organic Synthesis.  John Wiley & Sons.  ISBN 0-471-93623-5.  7.  s 4913 - 4920
• Gundersen, Lise-Lotte; Rise, Frode & Undheim, Kjell (1995). Zirconium Tetraisopropoxide, In Leo A. Paquette (ed.),  Encyclopedia of Reagents for Organic Synthesis.  John Wiley & Sons.  ISBN 0-471-93623-5.  8.  s 5581 - 5582
• Gundersen, Lise-Lotte; Rise, Frode & Undheim, Kjell (1995). Zirconium(III) Chloride, In Leo A. Paquette (ed.),  Encyclopedia of Reagents for Organic Synthesis.  John Wiley & Sons.  ISBN 0-471-93623-5.  8.  s 5580. - 5580.
• Gundersen, Lise-Lotte; Rise, Frode & Undheim, Kjell (1995). Zirconium(IV) Chloride, In Leo A. Paquette (ed.),  Encyclopedia of Reagents for Organic Synthesis.  John Wiley & Sons.  ISBN 0-471-93623-5.  8.  s 5580 - 5581
• Gundersen, Lise-Lotte; Bakkestuen, Anne Kristin Vibstad; Rise, Frode; Aasen, Arne Jørgen & Øverås, Harald (1994). 6-Halopurines in Palladium-Catalyzed Coupling with Organotin and Organozinc Reagents. Tetrahedron.  ISSN 0040-4020.  50, s 9743- 9756
• Hare, Brian J.; Aubin, Yves; Rise, Frode & Prestegard, James H. (1994). 13C-NMR Studies of Wheat Germ Agglutinin Interactions with N-Acetylglucosamine at a Magnetically oriented Bilayer Surface. Biochemistry.  ISSN 0006-2960.  33, s 10137- 10148
• Trost, Barry; Romero, D. L. & Rise, Frode (1994). Pd-Catalyzed Cycloisomerization to 1,2-Dialkylidenecycloalkanes. 2. Alternative Catalyst System. Journal of the American Chemical Society.  ISSN 0002-7863.  116, s 4268- 4278
• Borgen, Gerd; Rise, Frode & Dale, Johannes (1993). Conformations and Conformational Interconversions of Enantholactam. Magnetic Resonance in Chemistry.  ISSN 0749-1581.  31, s 855- 858
• Borgen, Gerd; Rise, Frode & Dale, Johannes (1993). Low-Temperature NMR of e-Caprolactam. Magnetic Resonance in Chemistry.  ISSN 0749-1581.  31, s 51- 53
• Gogoll, Adolf; Gundersen, Lise-Lotte; Valli, Mats & Rise, Frode (1993). Alkylation and Covalent Adduct Formation of 2-Oxopurine. Heterocycles.  ISSN 0385-5414.  36, s 231- 235
• Sandosham, Jessie; Rise, Frode & Undheim, Kjell (1993). Regioselective Substitution in Triflyloxypyrimidines and Chloropyrimidines using Zinc and Tin Reagents. Heterocycles.  ISSN 0385-5414.  35, s 235- 244
• Dale, Johannes; Rise, Frode; Rømming, Christian & Sigvartsen, Turid (1992). The Preparation and Conformational Studies of 5, 11, 11, 17, 17, 23, 23-Octamethyl-1, 3, 7, 9, 13, 15, 21-octaazaquinquecyclo [19.3.1.13,7.19,13.115,19] octacosane. Acta Chemica Scandinavica.  ISSN 0904-213X.  46, s 1200- 1203
• Gundersen, Lise-Lotte; Benneche, Tore; Rise, Frode; Gogoll, Adolf & Undheim, Kjell (1992). Regiochemistry and Stereochemistry in Pd(0)-Catalyzed Allylic Alkylation of Nucleoside Bases. Acta Chemica Scandinavica.  ISSN 0904-213X.  46, s 761- 771
• Gundersen, Lise-Lotte; Rise, Frode & Undheim, Kjell (1992). Aryl- and Alkynyltri-isopropoxytitanium Reagents in Regioselective Carbon-Carbon Bond Formation in Azines. Tetrahedron.  ISSN 0040-4020.  48, s 5647- 5656
• Bäckvall, Jan-Erling & Rise, Frode (1989). 2-(Phenylsulfonyl)-1,3-dienes in asymmetric Diels-Alder reactions with Chiral Enamines and Enol Ethers. Tetrahedron Letters.  ISSN 0040-4039.  30, s 5347- 5348
• Rise, Frode & Undheim, Kjell (1989). Sodium 2-Mercaptoethanesulfonate in Reversible Adduct Formation and Water Solubilization. Acta Chemica Scandinavica.  ISSN 0904-213X.  43, s 489- 492
• Trost, Barry; Lee, Donna C. & Rise, Frode (1989). A New Palladium Catalyst for Intramolecular Carbametallation of Enynes. Tetrahedron Letters.  ISSN 0040-4039.  30, s 651- 654
• Rise, Frode; Grace, David & Undheim, Kjell (1988). Ethynyltriisopropoxytitanium reactions with Pyrimidinones. Journal of Organometallic Chemistry.  ISSN 0022-328X.  338, s 341- 346
• Rise, Frode; Nordenson, Svein; Bouzga, Aud. M. & Undheim, Kjell (1988). Structure Determination of (Z)-5-Chloro-1-methyl-4H-4-phenacylidene-2(1H)-pyrimidinone. Acta Crystallographica.  ISSN 0365-110X.  C44, s 1298- 1300
• Rise, Frode & Trost, Barry (1987). A Reductive Cyclization of 1,6- and 1,7-Enynes. Journal of the American Chemical Society.  ISSN 0002-7863.  109, s 3161- 3163
• Klaveness, Jo; Rise, Frode & Undheim, Kjell (1986). Organotin Derivates in the Umpolung of 1,3-Dithian-2-ylides to 1,3-Dithian-2-ylium Salts. Journal of Organometallic Chemistry.  ISSN 0022-328X.  303, s 189- 195
• Klaveness, Jo; Rise, Frode & Undheim, Kjell (1986). Reactions of 1,3-Dithiolan-2-ylium and 1,3-Dithian-2-ylium Tetrafluoroborates and Ambident 2-Styryl Derivates. Acta Chemica Scandinavica.  ISSN 0904-213X.  B40, s 373- 380
• Klaveness, Jo; Rise, Frode & Undheim, Kjell (1986). Synthesis of 1,2-Dithiolan-2-ylium and 1,3-Dithian-2-ylium Tetrafluoroborate Salts. Acta Chemica Scandinavica.  ISSN 0904-213X.  B40, s 398- 399
• Rise, Frode; Høseggen, Tom & Undheim, Kjell (1986). Tetra-isopropoxyzirconium and Tri-isopropoxy-aluminum in Regioselective Reduction of Pyrimidinones. Journal of the Chemical Society. Perkin transactions 1.  ISSN 0300-922X.  s 849- 850
• Rasmussen, Asbjørn; Rise, Frode & Undheim, Kjell (1985). 1,2,4-Triazin-3(2H)-ones in Covalent Adduct Formations. Acta Chemica Scandinavica.  ISSN 0904-213X.  B39, s 235- 240
• Rise, Frode; Rømming, Christian & Undheim, Kjell (1985). Structure Investigations on Products from the Reaction of Organocopper, Organolithium and Organomagnesium Reagents with 2(1H)-Pyrimidinones. Acta Chemica Scandinavica.  ISSN 0904-213X.  B39, s 459- 468
• Rise, Frode & Undheim, Kjell (1985). Regioselectivity in Reactions of Alkynylmetal Complexes with Pyrimidinones. Journal of Organometallic Chemistry.  ISSN 0022-328X.  291, s 139- 144
• Rise, Frode & Undheim, Kjell (1985). Regioselectivity in the Reactions of Aryl-isopropoxy-titanium with Pyrimidinones. Journal of the Chemical Society. Perkin transactions 1.  ISSN 0300-922X.  s 1997- 1999
• Rise, Frode & Undheim, Kjell (1985). Regioselectivity in the Reductive Formation of Dihydro-5-halo-2(1H)-pyrimidinones. Acta Chemica Scandinavica.  ISSN 0904-213X.  B39, s 195- 201
• Rise, Frode; Ongstad, L.; Gacek, Michel & Undheim, Kjell (1983). Introduction of Carbon Substituents into Pyrimidines by Grignard Reagents. Acta Chemica Scandinavica.  ISSN 0904-213X.  B37, s 613- 615

Se alle arbeider i Cristin

• Berg, Henriette Engen; Hvinden, Ingvild Comfort; Sachse, Daniel; Skaga, Erlend; Lundanes, Elsa; Sandberg, Cecilie; Vik-Mo, Einar O.; Rise, Frode & Wilson, Steven Ray Haakon (2020). Observation of brain cancer cells’ molecular responses to chemotherapy.
• Xu, Kaiqi; Chatzitakis, Athanasios Eleftherios; Backe, Paul Hoff; Ruan, Qiushi; Tang, Junwang; Bjørås, Magnar; Rise, Frode & Norby, Truls Eivind (2020). The use of NMR to assess the activity of formate dehydrogenase biocatalysts for CO2 utilization.
• Hvinden, Ingvild Comfort; Rise, Frode; Berg, Henriette Engen; Lundanes, Elsa & Wilson, Steven Ray Haakon (2018). Approaches to untargeted metabolomics of glioblastoma: NMR and MS.
• Hvinden, Ingvild Comfort; Wilson, Steven Ray Haakon; Rise, Frode; Berg, Henriette Engen & Lundanes, Elsa (2018). Nuclear magnetic resonance spectroscopy based metabolomics discovers biomarkers of glioblastoma drug response. Vis sammendrag

  Glioblastoma is the most common and aggressive form of brain cancer. Even with comprehensive treatment regimes, patients face an expected survival of only 15 months. Currently, methods for assessing treatment response are lacking; it is difficult to accurately determine the efficacy of a treatment. The goal of the present study was to contribute to treatment assessment by scouting for metabolic biomarkers occurring in response to exposure to chemotherapeutic agents temozolomide (TMZ) and sepantronium bromide (YM155). Untargeted metabolomics of lysate from cultured glioblastoma cells was carried out with liquid state proton nuclear magnetic resonance (NMR) spectroscopy at resonance frequency 800 MHz. Spectral data were analyzed with two different multivariate statistical methods: principal component analysis (PCA) and partial least squares (PLS) regression. For YM155, two biomarker candidates were found: citric and lactic acid. Citric acid appeared to increase most in samples from cell lines less sensitive to YM155. Lactic acid decreased in all cell lines and was considered a more general biomarker of treatment exposure. TMZ-treated samples were not distinguishable from control samples, most likely due to too short exposure time (24 hours). Analyses with nano hydrophilic interaction liquid chromatography coupled with mass spectrometry (MS) corroborated the findings by NMR spectroscopy and statistical analyses. Both citric acid and lactic acid are biomarker candidates, but a more detailed understanding of their fluctuations in glioblastoma during treatment is needed. Nevertheless, they represent genuine candidates and should be considered for further in vivo magnetic resonance spectroscopy (MRS) studies. In the future, the biomarkers could be monitored with MRS, allowing a more unambiguous and personalized assessment of response to treatment in individual patients.

• Racz, Beatrix; Wilson, Steven Ray Haakon; Rise, Frode & Lundanes, Elsa (2018). Identification of a major UV absorbing compound in goose aqueous humour. Vis sammendrag

  About 5% of solar radiation comes from the ultraviolet (UV) region. It carries high energy and can do serious damage to living organisms. The eye of animals and humans is a critically exposed area and contains UV absorbing compounds like proteins, tryptophan, tyrosine, ascorbic acid and uric acid in the aqueous humour (AH) for protection. In addition, an unknown component (compound X) which causes red-shift in the UV absorbance spectrum at 254 nm has been observed in heavily exposed species like goose, which migrates at 10 000 m altitude. X is a major absorber. UV measurements confirmed the presence of a compound in geese which has higher absorption at 254 nm compared to other species. Compound X also has fluorescence activity that resembled indole-functionality. Aqueous humour samples from different species (goose, chicken, turkey) were measured by nuclear magnetic resonance spectroscopy (NMR). The proton NMR spectra did not show any specific high abundant compound in the goose eye at the aromatic region compared to the other species, thus NMR could not reveal what made the difference between in UV absorbance. Mass spectrometry with atmospheric pressure photoionization (APPI) has earlier showed that the molar mass of the compound X could be 149 g/mole, which suggests that compound X might be the indole: 5,6-dihydroxyindole (DHI). DHI has a central role in the biosynthesis of melanin which takes place in melanocyte cells. DHI tends to easily be polymerized and one of the results is a notable change in its solubility. It was not possible to obtain a suitable external standard which did not undergo auto-polymerization, mirroring the observations with the isolated compound.To further test the hypothesis of DHI being compound X, reversed phase (RP) high performance liquid chromatography (HPLC) and hydrophilic interaction liquid chromatography (HILIC) were performed. Ascorbic acid co-eluted with the most abundant peak (compound X) in RP-HPLC. In HILIC the most abundant peak was not ascorbic acid. Hence, compound X is not ascorbic acid, and subsequent experiments showed that it was neither the UV absorbing compounds tryptophan, tyrosine or uric acid. After using several analytical tools, the hypothesis that compound X is 5,6-dihydroxyindole was strengthened. However an external standard is still necessary to provide accurate information.

• Racz, Beatrix; Zawadzka, Malgorzata Elzbieta; Skytte Af Sätra, Jenny Marie; Ringvold, Amund; Rise, Frode; Lundanes, Elsa & Wilson, Steven Ray Haakon (2018). Identification of “compound X” in goose aqueous humour.
• Robertsen, Alison; Anderson, Don M.; Capper, A; Chan, Leo Lai; Erdner, Deana; Fæste, Christiane Kruse; Hernandez, Carlos Alfonso; Heck, Kenneth; Hugget, Megan; Hyndes, Glen; Ivanova, Lada; Lavery, Paul; McCarron, Pearse; McMahon, Kathryn; Miles, Christopher Owen; Miller, Molly; Parsons, Michael L.; Richen, Mindy L.; Rise, Frode; Samdal, Ingunn Anita; Sandvik, Morten; Smith, Tyler B. & Uhlig, Silvio (2018). CIGUA-PIRE Advancing Global Networks for Ciguatera in Tropical Oceans through Partnerships in International Research and Education.
• Furse, Samuel Robert; Jakubec, Martin; Rise, Frode; Williams, Hew; Rees, Catherine & Halskau, Øyvind (2017). Does the lipid fractio of Listeria innocua change as a function of the cell cycle?.
• Georgiev, Yordan Nikolaev; Paulsen, Berit Smestad; Kiyohara, Hiroaki; Číž, Milan; Ognyanov, Manol H.; Vašíček, Ondřej; Rise, Frode; Denev, Petko Nedyalkov; Yamada, Haruki; Lojek, Antonín; Kussovski, Vesselin; Barsett, Hilde; Krastanov, Albert Ivanov; Yanakieva, Irina Z. & Kratchanova, Maria G. (2017). Erratum to "The common lavender (Lavandula angustifolia Mill.) pectic polysaccharides modulate phagocytic leukocytes and intestinal Peyer's patch cells" (Carbohydr. Polym. (2017) 174 (948-959) (S0144861717307774) (10.1016/j.carbpol.2017.07.011)). Carbohydrate Polymers.  ISSN 0144-8617.  177, s 469- 470 . doi: 10.1016/j.carbpol.2017.09.037
• Jaabæk, Jon Atle Hoff; Rise, Frode; Miles, Christopher Owen & Wilkins, Alistair Lawrence (2017). Structure Elucidation of Three Microcystins by NMR Spectroscopy.
• Nguyen, Tien; Kenton, Nathaniel T.; Adu-Amprawun, Daniel; Okumu, Anthony A.; Zhang, Zhingao; Chen, Yong; Nguyen, Son; Xu, Jianyan; McCarron, Pearse; Kilkoyne, Jane; Rise, Frode; Wilkins, Alistair Lawrence; Owen, Christopher & Forsyth, Craig J. (2017). Final twist in marine toxin structural saga. Chemical & Engineering News, 95(49), December 14, 2017 [Science & Technology, News of The Week]. Chemical & engineering news (Print).  ISSN 0009-2347.  95(49), s 9- 9 . doi: http://pubs.acs.org/doi/abs/10.1021/cen-09549-notw7 Vis sammendrag

  In the mid-1990s, scientists started to notice cases across Europe of people falling ill from a new kind of shellfish food poisoning. The culprit, researchers discovered, was a family of marine toxins called azaspiracids. The structures of these amorphous toxins have been difficult for chemists to pin down, though some have come very close. A pair of papers from the laboratory of Craig J. Forsyth at Ohio State University now corrects the stereochemistry of a key position in azaspiracid-3 and details a total synthesis of the reassigned structure (Angew. Chem. Int. Ed. 2017, DOI: 10.1002/anie.201711006; Angew. Chem. Int. Ed. 2017, DOI: 10.1002/anie.201711008). A synthetic route to the azaspiracids along with accurate structures could help scientists develop assays to detect the toxins in food. Forsyth’s lab had been working on an azaspiracid synthesis in 2004 when K. C. Nicolaou, then at Scripps Research Institute California, reported a 96-step synthesis that revised the azaspiracids’ originally reported structure. Using the 2004 structure as a target, Forsyth’s group devised a new total synthesis. But when the chemists used liquid chromatography to compare their newly synthesized azaspiracid-3 with an authentic sample, they found that the compounds’ retention times didn’t match. After some head-scratching, Forsyth says, they suspected that the stereochemistry of an alcohol group may have been misassigned in the 2004 structure. Forsyth’s team definitively set the stereochemistry of the C20 alcohol, whereas the Nicolaou synthesis could have yielded either stereoisomer, possibly leading to a misassignment. The researchers chemically inverted the alcohol’s configuration, and were “overjoyed” when the resulting compound’s retention time matched that of the natural product. While previous total syntheses did succeed in making the correct natural product, they had misassigned one of the molecule’s 19 stereocenters. Nicolaou, now at Rice University, congratulated the team for their “meticulous” efforts that led to azaspiracid’s final structural revision. “That they were able to decipher the last detail for the correct structure as they did is a testament not only to their brilliant and scholarly work but also to the current powerful state of the art of total synthesis and the modern, high-resolution analytical techniques that support it.”

• Nytoft, Hans Peter; Kildahl-Andersen, Geir; Lindström, Sofie; Rise, Frode; Mitrovic, Danica; Dokovic, Natasa; Zivotic, Dragana R. & Stojanovic, Ksenija A (2017). Dehydroicetexanes in sediments and crude oils: Markers for Cupressaceae?.
• Stanić, Ana; Uhlig, Silvio; Miles, Christopher Owen; Skaar, Ida & Rise, Frode (2017). Preparation of Thiol Conjugates of the Mycotoxin Deoxynivalenol and their Occurrence in Nature.
• Kildahl-Andersen, Geir; Nytoft, Hans Peter; Weijers, Johan W. H. & Rise, Frode (2016). Structure elucidation of rearranged and degraded oleananes isolated from crude oils.
• Stanic, Ana; Uhlig, Silvio; Rise, Frode; Hofgaard, Ingerd Skow & Miles, Christopher Owen (2016). Identification of mercapturic acid conjugates of deoxynivalenol in cereals.
• Langseth, Eirin; Tråseth, Eline Aa.; Scheuermann, Margaret L.; Rise, Frode; Heyn, Richard H & Tilset, Mats (2014). Gold(III) complexes: Synthesis and characterization.
• Miles, Christopher O.; Wilkins, Alistair Lawrence; Holland, Patrick T.; McNabb, Paul; Rhodes, Lesley R.; Edwards, Pat; Larsen, Kristofer & Rise, Frode (2012). Rangiputamide from Prorocentrum lima: structure elucidation by NMR. Vis sammendrag

  Prorocentrum is a genus of benthic dinoflagellate microalgae with a world-wide distribution. P. lima is a species commonly found in northern harbours of New Zealand and produces okadaic acid analogues. During LC-MS (ESI+) screening of P. lima culture extracts, several strains including one isolated from Rangiputa, Rangaunu Harbour, were noted to produce an unusual N-containing compound MH+ 856 that eluted amongst the diol esters of okadaic acid. These strains were bulk-cultured and extracts of the cell pellets were fractionated by column chromatography, and the N-compound was isolated by preparative C18-HPLC in high purity (4.2 mg, MF C50H81NO10 from HRMS of MH+, 11 rings/double bonds). Acetylation followed by LC-MS indicated the presence of 4 reactive OH groups. The structure of rangiputamide (1) (1 mg) was deduced from an extensive array of 2D NMR experiments in CD3OD and d6-DMSO using double-solvent suppression. 1D and 2D NOESY and ROESY data is being analyzed to obtain stereochemical information. DMSO as solvent was useful in revealing the amide and hydroxyl protons and assigning some of the ether linkages and the epoxide. Prorocentrum spp. can produce several macrolides as well as okadaic acid, but this polyether structure is unprecedented. The matched pair of linked spiroketal 6-membered rings are similar to those in okadaic acid but with different substituent and linking groups. Rangiputamide was not detected in cultures of a strain of P.lima from Spain. It was non-toxic in mouse bioassay (i.p. injection) and not appreciably cytotoxic to Vero or P388 mammalian cells. The physiological or potential ecological function for 1 remains unknown.

• Miles, Christopher; Wilkins, Alistair L.; Holland, Patrick T.; Rhodes, Lesley R.; McNabb, Paul; Edwards, Pat; Rise, Frode & Larsen, Kristofer (2011). Rangiputamide from Prorocentrum lima: Structure elucidation by NMR.
• Austarheim, Ingvild Marie; Michaelsen, Terje Einar; Inngjerdingen, Marit; Rise, Frode; Diallo, Drissa & Paulsen, Berit Smestad (2009). Novel Pectin-like polysaccharides with immunomodulating properties from the bark of the malian medicinal tree Cola cordifolia.
• Gundersen, Lise-Lotte; Rise, Frode; Undheim, Kjell & Le Huerou, Y. (2009). Zirconium(IV) Chloride, In Leo A. Paquette (ed.),  Encyclopedia of Reagents for Organic Synthesis. 2. Ed.  John Wiley & Sons.  ISBN 978-0-470-01754-8.  13.  s 10965 - 10970
• Wilson, Steven Ray Haakon; Petersen, Dirk; Rise, Frode & Krauss, Stefan (2009). Exporing the chemistry of the anti-cancer drug cycopamine with LC-MS and NMR.
• Wilson, Steven Ray Haakon; Strand, Martin Frank; Rise, Frode; Petersen, Dirk; Lundanes, Elsa & Krauss, Stefan (2009). NMR and LC-MS Analysis of Natural and Acid-Induced Isomers of Cyclopamine.
• Miles, Christopher Owen; Huhn, J; Jeffrey, PD; Larsen, Kristoffer; Rundberget, Thomas; Sandvik, Morten; Samdal, Ingunn Anita; Rise, Frode & Shi, Y (2008). A structural basis for the reduced toxicity of dinophysistoxins-2.
• Tran, Bao Quoc; Greibrokk, Tyge; Lundanes, Elsa & Rise, Frode (2008). Multidimensional LC methods for proteomics.
• Wilson, Steven Ray Haakon; Greibrokk, Tyge; Lundanes, Elsa; Malerød, Helle; Malterud, Karl Egil; Petersen, Dirk & Rise, Frode (2008). Identification of the major metal compounds in blepharis aspera.
• Wilson, Steven Ray Haakon; Greibrokk, Tyge; Lundanes, Elsa; Malerød, Helle; Malterud, Karl Egil; Petersen, Dirk; Rise, Frode; Mmatli, Edward Eddie & Abegaz, Berhanu M (2008). Identification of the major metal compounds in blepharis aspera.
• Holm, Anders; Rise, Frode; Sessler, Nicole; Sollid, Ludvig Magne; Undheim, Kjell & Fleckenstein, Burkhard (2007). Specific Modification and Subsequent Mass Spectrometric Detection of Citrulline Containing Peptides. Vis sammendrag

  The posttranslational deimination of polypeptide-bound arginine residues is known as citrullination and is catalyzed by a family of Ca2+ dependent enzymes called peptidylarginine deiminases. Immune reactions to such citrulline containing proteins appear to be central in the immunopathogenesis of rheumatoid arthritis. Consequently there is a need to characterize which proteins in the inflamed joints of rheumatoid patients contain citrulline residues in situ. As demonstrated for a series of other posttranslational modifications, such as phosphorylation and glycosylation, the characterization of citrullinated proteins and peptides in complex mixtures is greatly facilitated by techniques allowing their specific enrichment and/or detection. So far such methods are not available for citrullinated peptides. As a first step towards the directed analysis of citrullinated proteins and peptides in rheumatoid arthritis, this study presents a method for the specific modification of peptide bound citrulline residues. This chemical reaction uses 2,3-butanedione and antipyrine as modifying reagents and is performed in 25-50 % TFA at 37°C. The modification shifts the mass of citrullinated peptides by 238 Da. NMR was applied to elucidate the structure of the modification product using N-butylurea as a model compound. Modified citrulline residues absorb at 464 nm enabling their selective detection and fractionation in liquid chromatography (LC). In order to verify the chemical structure of the modification and to investigate the generation of modification-specific fragment ions, modified citrulline containing peptides were subjected to collision induced dissociation experiments. Two fragments ions characteristic for modified citrulline residues were detected and will be presented. The usefulness of these signature ions to specifically detect modified citrullinated peptides in heterogeneous mixtures by nano LC-MS/MS will be discussed. Analysis was performed on ESI-ion trap, ESI-q-TOF and MALDI-TOF/TOF mass spectrometers.

• Larsen, Kristofer; Petersen, Dirk; Wilkins, Alistair L.; Goldstone, David; Arcus, Vickery; Rise, Frode & Miles, Christopher O. (2007). The C-35 Stereochemisties for Dinophysistoxin-1 and Dinophysistoxin-2 and its consequenses for biosynthesis and binding to protein phosphatases.
• Larsen, Kristofer; Wilkins, Alistair L.; Goldstone, David; Vickery, Arcus; Rise, Frode; Miles, Christopher O. & Petersen, Dirk (2007). The C-35 Stereochemistries for Dinophysistoxin-1 and Dinophysistoxin-2 and its consequences for biosynthesis and binding to protein phosphatases.
• Larsen, Kristofer; Petersen, Dirk; Wilkins, Alistair L.; Samdal, Ingunn; Sandvik, Morten; Rundberget, Thomas; Goldstone, D; Arcus, V.; Hovgaard, P.; Rise, Frode; Rehmann, N.; Hess, P. & Miles, Christopher O. (2007). Clarification of the C-35 Stereochemistries of Okadaic Acid, Dinophysistoxin-1, and Dinophysistoxin-2, and its consequences for binding to protein phosphatase.
• Larsen, Kristofer; Petersen, Dirk; Wilkins, Alistair L.; Samdal, Ingunn; Sandvik, Morten; Rundberget, Thomas; Goldstone, David; Arcus, Vickery; Hovgaard, Peter; Rise, Frode; Rehmann, N.; Hess, P. & Miles, Christopher O. (2007). Clarification of the C-35 Stereochemistries of Okadaic Acid, Dinophysistoxin-1, and Dinophysistoxin-2, and its consequences for binding to protein phosphatase.
• Malerød, Helle; Wilson, Steven Ray Haakon; Petersen, Dirk; Rise, Frode; Lundanes, Elsa & Greibrokk, Tyge (2007). Structure determination using on-line LC-MS/NMR.
• Rise, Frode (2007). 1H, 13C, 15N, 19F and 31P ONE DIMENSIONAL NMR SPECTROSCOPY.
• Rise, Frode (2007). Commercial service at the University of Oslo NMR center. [www ]. Vis sammendrag

  Commercial service: Depending upon the availability of available staff at the University of Oslo NMR Center and available instrument time the NMR Center is offering commercial services. The current price (January 2007) is NOK 400 (+25 % VAT) for each instrument hour on DPX200, DPX300 and Gemini200 when no NMR staff is present. The cost for setting up the experiments and processing data is additionally NOK 600 (+ 25 % VAT) for each hour spent (e.g. a total price of NOK 1000 (+ 25 % VAT) pr hour for part of the time). Most of the companies renting our facilities have employed students who have previously been trained at the University of Oslo NMR Center and consequently aquire the NMR data alone. Commercial users with sufficient training will sign a contract which gives them access to the low field instruments (Bruker DPX200, DPX300 and Gemini200) for a fee of NOK 400 (+ 25 % VAT) pr hour. Each instrument hour on the DRX500 instrument is costing NOK 500 (+25% VAT). In some cases customers are in need of the higher field and the higher sensitivity which is obatined at 600 MHz in combination with a cryo probe. The NMR Center is offering this service for the prices of NOK 800 (+ 25 % VAT) pr instrument hour. The cost for setting up the experiments, processing and evaluation (attempts at structure determinations) of the data is costing an additional NOK 600 (+25 % VAT) for each hour (e.g. a total price of NOK 1400 (+ 25 % VAT) pr hour for part of the time). All requests for commercial service shall be directed to the scientific leaders of the Center. Currently the University of Oslo NMR center services the following private companies: Alpharma, Oslo. Borregaard R&D, Sarpsborg. Caliber Synthesis, Fagernæs. Chemring Nobel, Sætre. Dynea, Lillestrøm. Drug Discovery Laboratories, Oslo. Invitrogen Dynal, Oslo. Lauras, Oslo. Nexans, Oslo. Pronova Biopharma, Sandefjord. Synthetica, Oslo.

• Rise, Frode (2007, 01. november). Energimangel i hjernen og 2-oxopropansyre. [Internett].  http://www.kjemi.uio.no/forskning/index.php?dok=akt&id=rise4. Vis sammendrag

  Når 13C merket 2-oxopropansyre ble gitt dyrene som energi isteden for 13C merket glukose ble det derimot ingen reduksjon i produksjonen av disse tre molekylene: noe som viser at sitronsyresyklusen ikke stopper opp når dyrene somanforgiftes. Med andre ord - hvis det er tilstrekkelig med 2-oxopropansyre til å lage ATP gjøres dette i sitronsyresyklusen og hjernen kan lettere overleve selv om glykolysen har stoppet opp. Tilslutt testet forskerne hva som skjedde når diazepam (7-chloro-1-methyl-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one), et beroligende og sløvende middel, ble gitt til dyrene. I utgangspunktet trodde forskerne at et sovende og somanforgiftet individ hadde lavere energibehov enn om dyret bare var somanforgiftet, men dette viste seg ikke å stemme, med diazepam-administrasjon ble hjernens energibehov ikke redusert. Hovedkonklusjonen på arbeidet er at hvis 2-oxopropansyre (pyruvat) gis ved somanforgiftning forventes det mindre skade på hjernen.

• Rise, Frode (2007, 15. september). Grønn te er kjempesunt!. [Internett].  http://www.kjemi.uio.no/publikum/index.php?dok=popart&id=15.
• Rise, Frode (2007, 15. august). Hvordan kan planter overleve i sterkt metallforurensede områder?. [Internett].  http://www.kjemi.uio.no/forskning/index.php?dok=akt&id=rise3.
• Rise, Frode (2007). ICONNMR and BACS sample changer manual.
• Rise, Frode (2007). KJM4250 - Organic NMR Spectroscopy. Laboratory Experiments - part 3. Heteronuclear 13C detected 2D NMR Spectroscopy. XHCORR (HETCOR) and COLOC Heteronuclear 1H detected 2D NMR Spectroscopy. HMQC, HSQC, HMBC H2BC (HSQC-COSY).
• Rise, Frode (2007). KJM5250 - Organic NMR Spectroscopy. Laboratory Experiments - part 2. Homonuclear 2D NMR Spectroscopy. COSY, TOCSY, NOESY, ROESY.
• Rise, Frode (2007). KJM5250 - Organic NMRSpectroscopy Laboratory Experiments - part 1. Pulse width determination, T1 relaxation time constant measurement, 1H-1H Decoupling, nOe Difference Spectroscopy, DEPT.
• Rise, Frode (2007). Linear Prediction in 1D NMR SPECTROSCOPY.
• Rise, Frode (2007). Linear Prediction in 2D NMR SPECTROSCOPY.
• Rise, Frode (2007, 15. september). Masterstudent Kristofer Larsen forklarer hvorfor to nesten like molekyler isolert fra blåskjell har dramatisk forskjell i giftighet. [Internett].  http://www.kjemi.uio.no/forskning/index.php?dok=akt&id=ris.
• Rise, Frode (2007, 17. desember). Metabolisme av propansyre i hjernen. [Internett].  http://www.kjemi.uio.no/forskning/aktuell/propansyre-i-hjern.
• Rise, Frode (2007). NMR i Life Science. Muligheter og eksempler. Vis sammendrag

  I foredraget vil eksempler på bruk av kjernemagnetisk resonans-spektropi (NMR) i biomedisinske problemstillinger bli presentert. Begrensinger med hensyn til substansmengder og renhet omtales. NMR-laboratoriets ved UiO, laboratoriets instrumentering og organisering vil presenteres. De forskjellige instrumentene er dedikert til forskjellige vitenskaplige formål. Samlokaliseringen gir stordriftsfordeler og mulighet for å utnytte ledig kapasitet på tvers av brukergruppene. Det nyeste instrumentet ipå laboratoriet danner en hjørnesten i "The University of Oslo Biomolecular Structure Platform". Hvis internettforbindelsen til Holmen Fjordhotell er god vil et reelt NMR-opptak vises. På grunn av begrenset personelltilgang må interesserte brukere enten innlede samarbeid eller selv lære seg metodene. Organisert grunnopplæring gis i modul 1 i kurset KJM-MEF4010: http://www.uio.no/studier/emner/matnat/ kjemi/KJM-MEF4010/v07/ og i det videregående emnet KJM5250 http://www. uio.no/studier/emner/matnat/kjemi/KJM5250/v07/. Ytterligere opplæring og innøving av metoder må foretas før man er kompetenet til å gjennomføre DNA/RNA- og proteinforsøk.

• Rise, Frode (2007, 01. september). NMR mot leddgikt. [Internett].  http://www.kjemi.uio.no/forskning/index.php?dok=akt&id=rise2.
• Rise, Frode (2007). Processing of XWINNMR-data from DPX200, DPX300 and DRX500, and TOPSPIN-data from AV600 and AVII600 with TOPSPIN 1.3 on a Windows 2003 Server.
• Rise, Frode (2007, 01. oktober). Studerer grantrær med NMR. [Internett].  http://www.kjemi.uio.no/publikum/index.php?dok=popart&id=14.
• Rise, Frode (2007). Window Functions in 1D NMR SPECTROSCOPY.
• Rise, Frode (2007). Zero Filling in 1D NMR SPECTROSCOPY.
• Rise, Frode (2007). Zero Filling in 2D NMR SPECTROSCOPY.
• Rise, Frode; Krengel, Ute; Gørbitz, Carl Henrik; Nissen-Meyer, Jon; Kristiansen, Per Eugen & Davies, William (2007). THE UNIVERSITY OF OSLO BIOMOLECULAR STRUCTURE PLATFORM. Vis sammendrag

  In-depth understanding of the mode of action of proteins and other biomolecules relies to a large extent on knowledge of their three-dimensional structures. Such knowledge is necessary for understanding bio-recognition and response processes, and is required for rational design of specific pharmacological reagents. Consequently it is essential for research in the molecular biosciences to determine the structures of biomolecules. We have applied for funding. with a grant proposal to EMBIO, to establish and manage a “Biomolecular Structure Platform” at the University of Oslo. The intention of the platform is to make methods for structure determination of biomolecules available to a larger group of the biomedical and biological communities. Moreover, it is also aimed to provide assistance in large-scale production and purification of proteins for structural studies. The principle objectives and purposes of the “Biomolecular Structure-Platform” are to: 1. Establish and develop methods for large-scale production and purification of isotope labeled proteins and peptides for structural analysis. 2. Determine the structure of proteins under investigation by the contributing groups, and thereby gain detailed insight into how these proteins function at a molecular level. 3. Serve other research groups that need assistance in production and purification of 13C, 15N and Se-Met labeled proteins and peptides. 4. Provide assistance to other research groups that wish to analyze the structure of proteins, peptides and other biomolecules by NMR-spectroscopy and X-ray crystallography, mainly in the context of collaborative research. 5. Strengthen the expertise in both three-dimensional structure- and function- analysis of biological macromolecules by performing a variety of experiments and employing different structure determination tools and also by educating Ph.D.- and Master- degree students in structure determination and analysis. 6. Strengthen the expertise in large-scale production and purification of proteins by educating Ph.D.- and Master- degree students in relevant techniques.

• Rise, Frode; Malerød, Helle; Mmatli, Edward Eddie; Wilson, Steven Ray Haakon; Lundanes, Elsa; Greibrokk, Tyge; Petersen, Dirk & Abegaz, Berhanu m (2007). Identification of Phenylethyl Glycosides from Blepharis aspera by LC-UV-SPE-NMR/MS Hyphenation.
• Rise, Frode; Mmatli, Edward Eddie; Malerød, Helle; Wilson, Steven Ray Haakon; Lundanes, Elsa; Greibrokk, Tyge; Petersen, Dirk & Abegaz, Berhanu m (2007). Identification of Phenylethyl Glycosides from Blepharis Aspera by LC-UV-SPE-NMR/MS Hyphenation.
• Rise, Frode & Petersen, Dirk (2007). Processing and plotting of 2D NMR spectra - TOCSY, NOESY and HSQC.
• Wilson, Steven Ray Haakon; Lundanes, Elsa; Rise, Frode & Greibrokk, Tyge (2007). On-line multidimensional LC-techniques. Determinations of known and unknown compounds in limited and complex samples..
• Holm, Anders; Rise, Frode; Sessler, Nicole; Sollid, Ludvig Magne; Undheim, Kjell & Fleckenstein, Burkhard (2006). Specific Modification and Subsequent Mass Spectrometric Detection of Citrulline Containing Peptide. Vis sammendrag

  The posttranslational deimination of polypeptide-bound arginine residues is known as citrullination and is catalyzed by a family of Ca2+ dependent enzymes called peptidylarginine deiminases. Immune reactions to such citrulline containing proteins appear to be central in the immunopathogenesis of rheumatoid arthritis. Consequently there is a need to characterize which proteins in the inflamed joints of rheumatoid patients contain citrulline residues in situ. As demonstrated for a series of other posttranslational modifications, such as phosphorylation and glycosylation, the characterization of citrullinated proteins and peptides in complex mixtures is greatly facilitated by techniques allowing their specific enrichment and/or detection. So far such methods are not available for citrullinated peptides. As a first step towards the directed analysis of citrullinated proteins and peptides in rheumatoid arthritis, this study presents a method for the specific modification of peptide bound citrulline residues. This chemical reaction uses 2,3-butanedione and antipyrine as modifying reagents and is performed in 25-50 % TFA at 37°C. The modification shifts the mass of citrullinated peptides by 238 Da. NMR was applied to elucidate the structure of the modification product using N-butylurea as a model compound. Modified citrulline residues absorb at 464 nm enabling their selective detection and fractionation in liquid chromatography (LC). In order to verify the chemical structure of the modification and to investigate the generation of modification-specific fragment ions, modified citrulline containing peptides were subjected to collision induced dissociation experiments. Two fragments ions characteristic for modified citrulline residues were detected and will be presented. The usefulness of these signature ions to specifically detect modified citrullinated peptides in heterogeneous mixtures by nano LC-MS/MS will be discussed. Analysis was performed on ESI-ion trap, ESI-q-TOF and MALDI-TOF/TOF mass spectrometers.

• Larsen, Kristofer; Petersen, Dirk; Wilkins, A.L.; Samdal, Ingunn; Sandvik, Morten; Rundberget, Thomas; Goldstone, G.; Arcus, V.; Hovgaard, Peter; Rise, Frode; Rehmann, N; Hess, Philipp & Miles, Christopher (2006). The C-35 Stereochemistries for dinophysistoxin - 1 and dinophysistoxin - 2 and its consequences for binding to proteinphosphatases.
• Larsen, Kristofer; Rise, Frode; Petersen, Dirk; Miles, Christopher O. & Wilkins, Alistair L. (2006). Clarification of the C-35 Stereochemistry of DTX-1.
• Larsen, Kristofer; Rise, Frode; Petersen, Dirk; Miles, Christopher O. & Wilkins, Alistair L. (2006). Clarification of the C-35 Stereochemistry of DTX-1.
• Malerød, Helle; Wilson, Steven Ray Haakon; Rise, Frode; Lundanes, Elsa & Greibrokk, Tyge (2006). Pre-concentration of compounds on a micro-solid phase extraction (SPE) column for LC-NMR analysis.
• Mmatli, Edward M; Rise, Frode; Abegaz, Berhanu m & Bezabih, Merhatibeb (2006). Phytochemical Studies on the aerial parts of Blepharis Aspera (Acatthaceae).
• Mmatli, Edward M; Rise, Frode; Abegaz, Berhanu m & Bezabih, Merhatibeb (2006). Phytochemical Studies on the aerial parts of Blepharis Aspera (Acatthaceae).
• Nebojsa, Simic; Wilson, Steven Ray; Malerød, Helle; Petersen, Dirk; Bobu, M M; Rise, Frode; Lundanes, Elsa & Greibrokk, Tyge (2006). Controlling LC-SPE-NMR Systems.
• Rise, Frode; Mmatli, Edward Eddie; Malerød, Helle; Wilson, Steven Ray Haakon; Lundanes, Elsa; Greibrokk, Tyge; Petersen, Dirk & Abegaz, Berhanu m (2006). Identification of Phenylethyl Glycosides from Blepharis aspera by LC-UV-SPE-NMR/MS Hyphenation. Vis sammendrag

  Conclusions Verbascoside and isoverbascoside were isolated and purified from Blepharis aspera. An in lab designed LC-UV-SPE-NMR/MS system was successfully used to separate the two compounds and to obtain their 1H NMR data online using a 30 micro liter LC-NMR probe.

• Mmatli, Edward M; Rise, Frode; Abegaz, Berhanu m & Bezabih, Merhatibeb (2005). Phytochemical studies on the aerial parts of Blepharis aspera (Acanthanceae).
• Rise, Frode (2005). Er det noe merkelig med veiledningen på HF og SV?. Uniforum.  ISSN 1891-5825.  (04), s 8- 8
• Rise, Frode; Petersen, Dirk; Nebojsa, Simic; Wilson, Steven Ray & Malerød, Helle (2005). LC-NMR.
• Bakkestuen, Anne Kristin Vibstad; Gundersen, Lise-Lotte & Rise, Frode (2005). Synthesis of agelasine E and agelasine analogs as well as 6-aryl and 6-alkenyl purines, and determination of their antimycobacterial activities.
• Aarnes, Halvor; Eriksen, Aud Else Berglen; Petersen, Dirk & Rise, Frode (2004). In Vivo 14N-NMR and 31P-NMR: intracellular pH in Norway spruce (Picea abies) seedlings grown on ammonium or nitrate.
• Rise, Frode; Petersen, Dirk; Nebojsa, Simic & Wilson, Steven Ray (2004). LC-NMR.
• Bråthe, Anders; Gundersen, Lise-Lotte & Rise, Frode (2004). Synthesis of purine derivatives with plant growth, antioxidant and cytotoxic properties.
• Bråthe, Anders; Gundersen, Lise-Lotte; Rise, Frode; Malterud, Karl Egil; Nissen-Meyer, Jon & Spilsberg, Bjørn (2004). Antioxidant and Cytotoxic Properties of Some 6-Substituted Purines.
• Negussie, Ayele Hailu; Gundersen, Lise-Lotte & Rise, Frode (2004). Synthesis of indolizine derivatives and screening of their antimycobacterial and 15-LO activity.
• Negussie, Ayele Hailu; Gundersen, Lise-Lotte; Rise, Frode & Østby, Ole Benny (2004). Antimycobacterial Activity of Substituted Indolizines.
• Teklu, Solomon; Gundersen, Lise-Lotte & Rise, Frode (2004). Synthesis, biological activities and electrochemical studies of indolizine derivatives.
• Teklu, Solomon; Gundersen, Lise-Lotte; Rise, Frode & Malterud, Karl Egil (2004). Indolizines as Novel Potent Inhibitors of 15-Lipoxygenase.
• Bråthe, Anders; Gundersen, Lise-Lotte; Rise, Frode; Nissen-Meyer, Jon & Spilsberg, Bjørn (2003). Cytotoxic Activity and Synthesis of 6-Alkenyl and 6-Alkenylpurines.
• Negusie, Ayele H.; Gundersen, Lise-Lotte & Rise, Frode (2003). Synthesis of Indolizines with Potential Inhibitory Activity against Mycobacterium Tuberculosis.
• Teklu, Solomon; Gundersen, Lise-Lotte; Malterud, Karl Egil; Rise, Frode & Østby, Ole Benny (2003). Indolizines as Novel Potent Inhibitors of 15-Lipoxygenase.
• Utenova, Bibigul; Malterud, Karl Egil & Rise, Frode (2003). Antioxidant Activity of O-Protected (-)-Epigallocatechin-3-gallates.
• Bråthe, Anders; Andresen, Geir; Gundersen, Lise-Lotte; Rise, Frode; Malterud, Karl Egil; Bast, Aalt & Haenen, Guido R. M. M. (2002). Antioxidant Properties of Cytokinin Analogs.
• Negusie, Ayele H.; Gundersen, Lise-Lotte; Rise, Frode & Østby, Ole Benny (2002). Synthesis of Indolizines with Potential Inhibitory Activity against Mycobacterium Tuberculosis.
• Teklu, Solomon; Gundersen, Lise-Lotte; Rise, Frode; Østby, Ole Benny & Malterud, Karl Egil (2002). Radical scavenging Properties of Indolizine Derivatives.
• Utenova, Bibigul & Rise, Frode (2002). Isolation and Derivatization of (-)-Epigallcatchecin Gallate.
• Bakkestuen, Anne Kristin Vibstad; Gundersen, Lise-Lotte & Rise, Frode (2001). Synthetic Studies towards Trixagol and Agelasine E.
• Andresen, Geir; Gundersen, Lise-Lotte; Nissen-Meyer, Jon; Spilsberg, Bjørn & Rise, Frode (2001). Cytotoxic Activity of 2-Oxopurine Derivatives.
• Andresen, Geir; Gundersen, Lise-Lotte & Rise, Frode (2001). Syntheses towards biologically active 2-oxopurine derivatives.
• Andresen, Geir; Gundersen, Lise-Lotte & Rise, Frode (2001). Synthesis of 2-Oxopurine Derivatives as Potential HIV Reverse Transcriptase Inhibitors.
• Andresen, Geir; Gundersen, Lise-Lotte & Rise, Frode (2001). Synthesis of 2-Oxopurine Derivatives as Potential HIV Reverse Transcriptase Inhibitors.
• Antonsen, Øyvind Gunnar; Kristensen, Tom Arne; Langhelle, B.; Fosnes, K.; Larsen, V.; Gundersen, Lise-Lotte; Rise, Frode; Bast, Aalt; Custers, Ilse & Haenen, Guido R. M. M. (2001). Synthesis of Indolizines and Pyrrolo[1,2-b]pyridazine with Antioxidant Properties.
• Bakkestuen, Anne Kristin Vibstad; Gundersen, Lise-Lotte & Rise, Frode (2001). Synthetic Studies towards Trixagol and Agelasine E.
• Bråthe, Anders; Gundersen, Lise-Lotte; Rise, Frode & Malterud, Karl Egil (2001). Antioxidant Properties of some Cytokinin Analogues.
• Bråthe, Anders; Gundersen, Lise-Lotte; Rise, Frode & Malterud, Karl Egil (2001). Antioxidant properties of some cytokinin analogues.
• Bråthe, Anders; Gundersen, Lise-Lotte; Rise, Frode & Malterud, Karl Egil (2001). Antioxidant properties of some cytokinin analogues.
• Gundersen, Lise-Lotte; Rise, Frode & Undheim, Kjell (2001). Methylzirconium Tributoxide. [www ].
• Gundersen, Lise-Lotte; Rise, Frode & Undheim, Kjell (2001). Zirconium Tetraisopropoxide. [www ].
• Gundersen, Lise-Lotte; Rise, Frode & Undheim, Kjell (2001). Zirconium(III) Chloride.
• Gundersen, Lise-Lotte; Rise, Frode; Undheim, Kjell; Aguilar, E. & Garcia-Garcia, P (2001). Titanium(IV) Chloride. [www ].
• Gundersen, Lise-Lotte; Rise, Frode; Undheim, Kjell & Le Huerou, Y (2001). Zirconium(IV) Chloride. [www ].
• Gundersen, Lise-Lotte; Rise, Frode; Undheim, Kjell & Mendez-Andino, J. (2001). Titanium(III) Chloride. [www ].
• Negusie, Ayele H.; Gundersen, Lise-Lotte; Rise, Frode & Østby, Ole Benny (2001). Synthesis of Indolizines with Potential Inhibitory Activity against Mycobacterium Tuberculosis.
• Rise, Frode; Efskind, Jon; Falch-Pedersen, Mette Lene; Klaveness, Jo & Gunnes, Sølvi (2001). Kjell Undheim Symposium in Organic Chemistry 1-2 November 2001 University of Oslo, ISBN 82-996093-0-5.
• Teklu, Solomon; Gundersen, Lise-Lotte; Rise, Frode; Østby, Ole Benny & Malterud, Karl Egil (2001). Radical scavenging properties of indolizine derivatives.
• Østby, Ole Benny; Gundersen, Lise-Lotte & Rise, Frode (2001). Syntese av 1-substituerte ondoliziner som potensielle antioksidanter.
• Andresen, Geir; Gundersen, Lise-Lotte & Rise, Frode (2000). Synthesis of 6-Substituted 2-Oxopurines as Potential Plant Hormones.
• Netland, Kjetil Andreas; Gundersen, Lise-Lotte & Rise, Frode (2000). 13C Assignment of Cyclopropenone Resonances.
• Netland, Kjetil Andreas; Gundersen, Lise-Lotte & Rise, Frode (2000). An improved Synthesis of Dialkylcyclopropenones.
• Netland, Kjetil Andreas; Gundersen, Lise-Lotte & Rise, Frode (2000). Syntese av syklopropenoner.
• Spilsberg, Bjørn; Rise, Frode; Petersen, Dirk & Nissen-Meyer, Jon (2000). SECRETION OF THYMIDINE BY HYBRIDOMA CELLS. Vis sammendrag

  Myeloma and hybridoma cells have been reported to secrete a low molecular weight growth inhibitory factor (Rønning et al., 1991, Cytotechnology 7, 15-24; Røe, Ø. et al., 1999, Biochem. Biophys. Res. Commun. 254, 138-142). The factor was identified as thymidine by NMR spectroscopy after isolation to homogeneity from hybridoma cell cultures by ultrafiltration, dialysis concentration and reverse phase chromatography under acidic and neutral conditions. Taken together, the results suggest that hybridoma cells and possibly myeloma cells secrete thymidine.

• Spilsberg, Bjørn; Rise, Frode; Petersen, Dirk; Rønning, Øystein W. & Nissen-Meyer, Jon (2000). The low-molecular-weight "growth inhibitory factor" produced by hybridoma cell culture identifed as thymidine by NMR-spectroscopy.
• Spilsberg, Bjørn; Rise, Frode; Petersen, Dirk; Rønning, Øystein W. & Nissen-Meyer, Jon (2000). The low-molecular-weight "growth inhibitory factor" produced by hybridoma cell cultures identified as thymidine by NMR-spectroscopy. Vis sammendrag

  Myeloma and hybridoma cells have been reported to secrete a low-molecular-weight growth inhibitory factor (1, 2). This factor was isolated to homogeneity from the media (4.0 liters) of hybridoma cell cultures by ultrafiltration, ¿dialysis concentration¿ and reverse phase chromatography under acidic and neutral conditions. The inhibitory factor was identified as thymidine by NMR spectroscopy. (1) Rønning, Ø.W., Schartum, M., Winsnes, A. and Lindberg, G. (1991) Growth limitation in hybridoma cell cultures: The role of inhibitory or toxic metabolites. Cytotechnology 7, 15-24. (2) Røe, Ø., Brondz, I., Rønning, Ø. and Nissen-Meyer, J. (1999) Isolation of a low-molecular-weight growth inhibitory factor from hybridoma cell cultures. Biochem. Biophys. Res. Commun. 254, 138-142.

• Østby, Ole Benny; Gundersen, Lise-Lotte & Rise, Frode (2000). Synthesis of 1-Substituted 7-Cyano-2,3-diphenylindolizines as Potential Antioxidants.
• Østby, Ole Benny; Rise, Frode & Gundersen, Lise-Lotte (2000). Assignment of 13C Resonances of Indolizines Using Optimised COLOC, HMBC and INADEQUATE NMR.
• Nolsøe, Jens M. J.; Gundersen, Lise-Lotte & Rise, Frode (1999). Syntese av 8-halopuriner, samt Pd-katalyserte krysskoblinger på 6,8-dihalopuriner med organometalliske reagenser.
• Rise, Frode (1999). A Different Kind of Lecture. Vis sammendrag

  http://www.bruker.se/unmr99ma.htm A different kind of lecture! Experiences since 1995 with NMR spectrometers integrated on the University of Oslo Network and the Internet

• Bråthe, Anders; Gundersen, Lise-Lotte & Rise, Frode (1998). Syntese av cytokininanaloger.
• Bråthe, Anders; Gundersen, Lise-Lotte; Rise, Frode; Eriksen, Aud Else Berglen & Wang, Linnea (1998). Synthesis of Cytokinin Analogues.
• Nolsøe, Jens M. J.; Rise, Frode & Gundersen, Lise-Lotte (1998). Synthesis of 6,8-Dihalopurines and Studies of their Reactivity in Cross Coupling Reactions.
• Øverås, Anniken Thomsen; Gundersen, Lise-Lotte & Rise, Frode (1998). Nucleophilic Addition and Diels-Alder Reactions on 6-Vinylpurines.
• Bråthe, Anders; Rise, Frode & Gundersen, Lise-Lotte (1997). Heck koblinger på vinylpurin; syntese av potensielle cytokininer.
• Nasir, Achmad I.; Gundersen, Lise-Lotte; Rise, Frode; Bast, Aalt & Haenen, Guido R. M. M. (1997). Syntese av indolisiner med antioksidant egenskaper.
• Nasir, Achmad Izzudin; Gundersen, Lise-Lotte & Rise, Frode (1997). Syntese av syklopropenoner og indoliziner med antioksidantegenskaper.
• Nolsøe, Jens M. J.; Rise, Frode & Gundersen, Lise-Lotte (1997). Regiokjemiske studier av kobling mellom 6,8-dihalopuriner og organometalliske reagenser.
• Øverås, Anniken Thomsen; Gundersen, Lise-Lotte & Rise, Frode (1997). Diels-Alder- og addisjonsreaksjoner på 6-vinylpuriner.
• Andresen, Geir; Gundersen, Lise-Lotte & Rise, Frode (1996). Regioselective Addition of Grignard Reagents to 2-Purinone Derivatives.
• Andresen, Geir; Gundersen, Lise-Lotte & Rise, Frode (1996). Regioselektiv C-C bindingsdannelse på benzylerte 2-oksopuriner.
• Andresen, Geir; Gundersen, Lise-Lotte & Rise, Frode (1996). Syntese og N-benzylering av 1,3-dihydro-2H-purinon. Addisjonsreaksjoner med N-benzylerte 1,3-dihydro-2H-purinoner.
• Gundersen, Lise-Lotte; Langli, Geir; Rise, Frode & Thomsen, Anniken (1996). Pd-Catalyzed C-C Bond Formation in Purines.
• Langli, Geir; Gundersen, Lise-Lotte & Rise, Frode (1996). 2,6-Dihalopuriner i regioselektive palladiumkatalyserte koblinger med organotinnreagenser.
• Langli, Geir; Gundersen, Lise-Lotte & Rise, Frode (1996). Regioselektive palladiumkatalyserte koblinger mellom 2,6-dihalopuriner og organometaller.
• Thomsen, Anniken; Gundersen, Lise-Lotte & Rise, Frode (1996). Nukleofile addisjoner og sykloaddisjoner til 6-vinylpuriner.
• Andersen, Geir; Gundersen, Lise-Lotte; Lundmark, Max; Sundell, Staffan & Rise, Frode (1995). Dannelse og Alkylering av 2-Oxopurin. Addisjon av Grignard reagenser til et alkylert 2-oxopurinium sal.
• Andresen, Geir; Gundersen, Lise-Lotte & Rise, Frode (1995). Structure Determination of 2-Oxopurine Derivatives with NMR.
• Gundersen, Lise-Lotte; Langli, Geir; Rise, Frode & Øverås, Harald (1995). Strategier for karbon - karbon bindingsdannelse i puriner.
• Langli, Geir; Gundersen, Lise-Lotte & Rise, Frode (1995). 2,6-Diklorpuriner i Palladium-katalyserte koblinger med organotinn og organosink reagenser.
• Ugland, Sigurd; Gundersen, Lise-Lotte; Rise, Frode; Bast, Aalt & Haenen, Guido R. M. M. (1995). Syntese av potensielle antioksidanter og nevrobeskyttende forbindelser.
• Øverås, Harald; Gundersen, Lise-Lotte; Rise, Frode & Aasen, Arne Jørgen (1995). 6-Halopuriner i palladium-katalyserte koblinger med organosink reagenser.
• Øverås, Harald; Gundersen, Lise-Lotte; Rise, Frode & Aasen, Arne Jørgen (1995). Palladiumkatalyserte koblingsreaksjoner mellom organosinkreagenser og 6-halopuriner og forsøk på syntese av 9-benzyl-6-trialkyltinnpuriner.
• Bakkestuen, Anne Kristin; Gundersen, Lise-Lotte; Rise, Frode & Aasen, Arne Jørgen (1994). Palladiumkatalyserte koblingsreaksjoner mellom tetraorganotinnforbindelser og N-benzylert 6-klorpurin.
• Gundersen, Lise-Lotte; Bakkestuen, Anne Kristin; Aasen, Arne Jørgen; Øverås, Harald & Rise, Frode (1994). Pd-Catalyzed Carbon - Carbon Bond Formation in Purines.

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