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Ellefsen, Christiane Færestrand; Wold, Christian Winther; Wilkins, Alistair L.; Rise, Frode & Samuelsen, Anne Berit C.
(2021).
Water-soluble mannogalactan and β-glucans from Pleurotus eryngii fruiting bodies, their activity and affinity for TLR2 and dectin-1 receptors.
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Uhlig, Silvio; Kryuchkov, Fedor; Gwinn, Jesse; Ivanova, Lada; Fæste, Christiane Kruse & Miles, Christopher Owen
[Show all 11 contributors for this article]
(2020).
CIGUAPIRE: Advancing Global Strategies and Understanding on the Origin of Ciguatera Fish Poisoning in Tropical Oceans.
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Xu, Kaiqi; Chatzitakis, Athanasios Eleftherios; Backe, Paul Hoff; Ruan, Qiushi; Tang, Junwang & Bjørås, Magnar
[Show all 8 contributors for this article]
(2020).
The use of NMR to assess the activity of formate dehydrogenase biocatalysts for CO2 utilization.
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Berg, Henriette Engen; Hvinden, Ingvild Comfort; Sachse, Daniel; Skaga, Erlend; Lundanes, Elsa & Sandberg, Cecilie
[Show all 9 contributors for this article]
(2020).
Observation of brain cancer cells’ molecular responses to chemotherapy
.
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Robertsen, Alison; Anderson, Don M.; Capper, A; Chan, Leo Lai; Erdner, Deana & Fæste, Christiane Kruse
[Show all 23 contributors for this article]
(2018).
CIGUA-PIRE Advancing Global Networks for Ciguatera in Tropical Oceans through Partnerships in International Research and Education.
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Racz, Beatrix; Zawadzka, Malgorzata Elzbieta; Skytte Af Sätra, Jenny Marie; Ringvold, Amund; Rise, Frode & Lundanes, Elsa
[Show all 7 contributors for this article]
(2018).
Identification of “compound X” in goose aqueous humour.
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Hvinden, Ingvild Comfort; Rise, Frode; Berg, Henriette Engen; Lundanes, Elsa & Wilson, Steven Ray Haakon
(2018).
Approaches to untargeted metabolomics of glioblastoma: NMR and MS.
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Georgiev, Yordan Nikolaev; Paulsen, Berit Smestad; Kiyohara, Hiroaki; Číž, Milan; Ognyanov, Manol H. & Vašíček, Ondřej
[Show all 15 contributors for this article]
(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,
p. 469–470.
doi:
10.1016/j.carbpol.2017.09.037.
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Nguyen, Tien; Kenton, Nathaniel T.; Adu-Amprawun, Daniel; Okumu, Anthony A.; Zhang, Zhingao & Chen, Yong
[Show all 14 contributors for this article]
(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),
p. 9–9.
doi:
10.1021/cen-09549-notw7.
Show summary
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.”
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Nytoft, Hans Peter; Kildahl-Andersen, Geir; Lindström, Sofie; Rise, Frode; Mitrovic, Danica & Dokovic, Natasa
[Show all 8 contributors for this article]
(2017).
Dehydroicetexanes in sediments and crude oils: Markers for Cupressaceae?
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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?
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Kildahl-Andersen, Geir; Nytoft, Hans Peter; Weijers, Johan W. H. & Rise, Frode
(2016).
Structure elucidation of rearranged and degraded oleananes isolated from crude oils.
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Stanic, Ana; Uhlig, Silvio; Rise, Frode; Hofgaard, Ingerd Skow & Miles, Christopher Owen
(2016).
Identification of mercapturic acid conjugates of deoxynivalenol in cereals.
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Uhlig, Silvio; Kryuchkov, Fedor; Gwinn, Jesse; Ivanova, Lada; Fæste, Christiane Kruse & Miles, Christopher Owen
[Show all 11 contributors for this article]
(2014).
CiguaPIRE: Norwegian contributions to advancing the global understanding of ciguatera.
Show summary
The international CiguaPIRE project focuses on three major research objectives: 1) To evaluate epiphyte and Gambierdiscus community diversity and macrophyte host selectivity in Caribbean coral reef ecosystems; 2) To characterize the meta-metabolome of these communities, structurally elucidate key metabolites, and develop methods to evaluate their toxicity and functional role; and 3) To identify chemical biomarkers in reef bio-indicator species and model their fate in reef food webs. The Norwegian CiguaPIRE project team, in close collaboration with the US and Canadian teams, primarily contribute towards objective 2. We have studied the mass spectrometric characteristics of Caribbean ciguatoxins (CTX), i.e. the epimers C-CTX-1 and -2, using a sensitive UHPLC–HRMS/MS approach in order to identify product ions of diagnostic value. Based on these data, we were able to determine the chemical structures of two analogues, C-CTX-3 and -4. By applying reduction and oxidation reactions, we showed that C-CTX-1 and -2 can be chemically converted into C-CTX-3 and -4. Our recent efforts concerned the optimization of a simple derivatization method for CTX-1 and -2, leading to signal enhancement in mass spectrometry-based detection of the toxins.
Additional collaborative efforts have been focused on cross-species comparison of hepatic biotransformation by in vitro metabolism assays. Using a variety of wild caught fish species from the northern Gulf of Mexico, livers were harvested and used in the preparation of microsomes. Oxidative and conjugative metabolism reactions were studied using semi-pure CTX-1 and -2. The experiments identified a detoxification pathway that had not previously been described for this class of toxins in fish, and which was absent when we performed corresponding experiments using rat or human liver microsomes. These data will aid in our trans-ocean efforts to better understand CTX toxicity and pathways of detoxification in fish.
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Langseth, Eirin; Tråseth, Eline Aa.; Scheuermann, Margaret L.; Rise, Frode; Heyn, Richard H & Tilset, Mats
(2014).
Gold(III) complexes: Synthesis and characterization.
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Miles, Christopher O.; Wilkins, Alistair Lawrence; Holland, Patrick T.; McNabb, Paul; Rhodes, Lesley R. & Edwards, Pat
[Show all 8 contributors for this article]
(2012).
Rangiputamide from Prorocentrum lima: structure elucidation by NMR.
Show summary
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.
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Miles, Christopher; Wilkins, Alistair L.; Holland, Patrick T.; Rhodes, Lesley R.; McNabb, Paul & Edwards, Pat
[Show all 8 contributors for this article]
(2011).
Rangiputamide from Prorocentrum lima: Structure elucidation by NMR.
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Gundersen, Lise-Lotte; Rise, Frode; Undheim, Kjell & Le Huerou, Y.
(2009).
Zirconium(IV) Chloride.
In Paquette, Leo A. (Eds.),
Encyclopedia of Reagents for Organic Synthesis. 2. Ed.
John Wiley & Sons.
ISSN 978-0-470-01754-8.
p. 10965–10970.
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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.
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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.
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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.
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Wilson, Steven Ray Haakon; Greibrokk, Tyge; Lundanes, Elsa; Malerød, Helle; Malterud, Karl Egil & Petersen, Dirk
[Show all 9 contributors for this article]
(2008).
Identification of the major metal compounds in blepharis aspera.
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Miles, Christopher Owen; Huhn, J; Jeffrey, PD; Larsen, Kristoffer; Rundberget, Thomas & Sandvik, Morten
[Show all 9 contributors for this article]
(2008).
A structural basis for the reduced toxicity of dinophysistoxins-2.
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Wilson, Steven Ray Haakon; Greibrokk, Tyge; Lundanes, Elsa; Malerød, Helle; Malterud, Karl Egil & Petersen, Dirk
[Show all 7 contributors for this article]
(2008).
Identification of the major metal compounds in blepharis aspera.
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Rise, Frode
(2007).
Commercial service at the University of Oslo NMR center.
Show summary
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.
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Rise, Frode
(2007).
NMR mot leddgikt.
[Internet].
http://www.kjemi.uio.no/forskning/index.php?dok=akt&id=rise2.
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Rise, Frode
(2007).
Grønn te er kjempesunt!
[Internet].
http://www.kjemi.uio.no/publikum/index.php?dok=popart&id=15.
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Rise, Frode
(2007).
Energimangel i hjernen og 2-oxopropansyre.
[Internet].
http://www.kjemi.uio.no/forskning/index.php?dok=akt&id=rise4.
Show summary
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.
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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.
Show summary
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.
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Larsen, Kristofer; Petersen, Dirk; Wilkins, Alistair L.; Samdal, Ingunn; Sandvik, Morten & Rundberget, Thomas
[Show all 13 contributors for this article]
(2007).
Clarification of the C-35 Stereochemistries of Okadaic Acid, Dinophysistoxin-1, and Dinophysistoxin-2, and its consequences for binding to protein phosphatase.
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Rise, Frode
(2007).
NMR i Life Science. Muligheter og eksempler.
Show summary
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.
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Malerød, Helle; Wilson, Steven Ray Haakon; Petersen, Dirk; Rise, Frode; Lundanes, Elsa & Greibrokk, Tyge
(2007).
Structure determination using on-line LC-MS/NMR.
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Larsen, Kristofer; Petersen, Dirk; Wilkins, Alistair L.; Goldstone, David; Arcus, Vickery & Rise, Frode
[Show all 7 contributors for this article]
(2007).
The C-35 Stereochemisties for Dinophysistoxin-1 and Dinophysistoxin-2 and its consequenses for biosynthesis and binding to protein phosphatases.
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Rise, Frode; Mmatli, Edward Eddie; Malerød, Helle; Wilson, Steven Ray Haakon; Lundanes, Elsa & Greibrokk, Tyge
[Show all 8 contributors for this article]
(2007).
Identification of Phenylethyl Glycosides from Blepharis Aspera by LC-UV-SPE-NMR/MS Hyphenation.
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Rise, Frode; Krengel, Ute; Gørbitz, Carl Henrik; Nissen-Meyer, Jon; Kristiansen, Per Eugen & Davies, William
(2007).
THE UNIVERSITY OF OSLO BIOMOLECULAR STRUCTURE PLATFORM.
Show summary
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.
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Larsen, Kristofer; Wilkins, Alistair L.; Goldstone, David; Vickery, Arcus; Rise, Frode & Miles, Christopher O.
[Show all 7 contributors for this article]
(2007).
The C-35 Stereochemistries for Dinophysistoxin-1 and Dinophysistoxin-2 and its consequences for biosynthesis and binding to protein phosphatases.
-
Rise, Frode; Malerød, Helle; Mmatli, Edward Eddie; Wilson, Steven Ray Haakon; Lundanes, Elsa & Greibrokk, Tyge
[Show all 8 contributors for this article]
(2007).
Identification of Phenylethyl Glycosides from Blepharis aspera by LC-UV-SPE-NMR/MS Hyphenation.
-
Larsen, Kristofer; Petersen, Dirk; Wilkins, A.L.; Samdal, Ingunn; Sandvik, Morten & Rundberget, Thomas
[Show all 13 contributors for this article]
(2006).
The C-35 Stereochemistries for dinophysistoxin - 1 and dinophysistoxin - 2 and its consequences for binding to proteinphosphatases.
-
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.
Show summary
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.
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Rise, Frode; Mmatli, Edward Eddie; Malerød, Helle; Wilson, Steven Ray Haakon; Lundanes, Elsa & Greibrokk, Tyge
[Show all 8 contributors for this article]
(2006).
Identification of Phenylethyl Glycosides from Blepharis aspera by LC-UV-SPE-NMR/MS Hyphenation.
Show summary
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.
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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.
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Larsen, Kristofer; Rise, Frode; Petersen, Dirk; Miles, Christopher O. & Wilkins, Alistair L.
(2006).
Clarification of the C-35 Stereochemistry of DTX-1.
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Larsen, Kristofer; Rise, Frode; Petersen, Dirk; Miles, Christopher O. & Wilkins, Alistair L.
(2006).
Clarification of the C-35 Stereochemistry of DTX-1.
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Mmatli, Edward M; Rise, Frode; Abegaz, Berhanu m & Bezabih, Merhatibeb
(2006).
Phytochemical Studies on the aerial parts of Blepharis Aspera (Acatthaceae).
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Mmatli, Edward M; Rise, Frode; Abegaz, Berhanu m & Bezabih, Merhatibeb
(2006).
Phytochemical Studies on the aerial parts of Blepharis Aspera (Acatthaceae).
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Rise, Frode
(2005).
Er det noe merkelig med veiledningen på HF og SV?
Uniforum.
ISSN 1891-5825.
p. 8–8.
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Rise, Frode; Petersen, Dirk; Nebojsa, Simic; Wilson, Steven Ray & Malerød, Helle
(2005).
LC-NMR.
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Mmatli, Edward M; Rise, Frode; Abegaz, Berhanu m & Bezabih, Merhatibeb
(2005).
Phytochemical studies on the aerial parts of Blepharis aspera (Acanthanceae).
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Negussie, Ayele Hailu; Gundersen, Lise-Lotte; Rise, Frode & Østby, Ole Benny
(2004).
Antimycobacterial Activity of Substituted Indolizines.
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Teklu, Solomon; Gundersen, Lise-Lotte; Rise, Frode & Malterud, Karl Egil
(2004).
Indolizines as Novel Potent Inhibitors of 15-Lipoxygenase.
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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.
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Rise, Frode; Petersen, Dirk; Nebojsa, Simic & Wilson, Steven Ray
(2004).
LC-NMR.
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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.
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Bråthe, Anders; Gundersen, Lise-Lotte; Rise, Frode; Nissen-Meyer, Jon & Spilsberg, Bjørn
(2003).
Cytotoxic Activity and Synthesis of 6-Alkenyl and 6-Alkenylpurines.
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Teklu, Solomon; Gundersen, Lise-Lotte; Malterud, Karl Egil; Rise, Frode & Østby, Ole Benny
(2003).
Indolizines as Novel Potent Inhibitors of 15-Lipoxygenase.
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Utenova, Bibigul; Malterud, Karl Egil & Rise, Frode
(2003).
Antioxidant Activity of O-Protected (-)-Epigallocatechin-3-gallates.
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Negusie, Ayele H.; Gundersen, Lise-Lotte & Rise, Frode
(2003).
Synthesis of Indolizines with Potential Inhibitory Activity against Mycobacterium Tuberculosis.
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Utenova, Bibigul & Rise, Frode
(2002).
Isolation and Derivatization of (-)-Epigallcatchecin Gallate.
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Teklu, Solomon; Gundersen, Lise-Lotte; Rise, Frode; Østby, Ole Benny & Malterud, Karl Egil
(2002).
Radical scavenging Properties of Indolizine Derivatives.
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Negusie, Ayele H.; Gundersen, Lise-Lotte; Rise, Frode & Østby, Ole Benny
(2002).
Synthesis of Indolizines with Potential Inhibitory Activity against Mycobacterium Tuberculosis.
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Gundersen, Lise-Lotte; Rise, Frode; Undheim, Kjell; Aguilar, E. & Garcia-Garcia, P
(2001).
Titanium(IV) Chloride.
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Andresen, Geir; Gundersen, Lise-Lotte; Nissen-Meyer, Jon; Spilsberg, Bjørn & Rise, Frode
(2001).
Cytotoxic Activity of 2-Oxopurine Derivatives.
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Negusie, Ayele H.; Gundersen, Lise-Lotte; Rise, Frode & Østby, Ole Benny
(2001).
Synthesis of Indolizines with Potential Inhibitory Activity against Mycobacterium Tuberculosis.
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Bråthe, Anders; Gundersen, Lise-Lotte; Rise, Frode & Malterud, Karl Egil
(2001).
Antioxidant Properties of some Cytokinin Analogues.
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Andresen, Geir; Gundersen, Lise-Lotte & Rise, Frode
(2001).
Synthesis of 2-Oxopurine Derivatives as Potential HIV Reverse Transcriptase Inhibitors.
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Bakkestuen, Anne Kristin Vibstad; Gundersen, Lise-Lotte & Rise, Frode
(2001).
Synthetic Studies towards Trixagol and Agelasine E.
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Antonsen, Øyvind Gunnar; Kristensen, Tom Arne; Langhelle, B.; Fosnes, K.; Larsen, V. & Gundersen, Lise-Lotte
[Show all 10 contributors for this article]
(2001).
Synthesis of Indolizines and Pyrrolo[1,2-b]pyridazine with Antioxidant Properties.
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Andresen, Geir; Gundersen, Lise-Lotte & Rise, Frode
(2001).
Synthesis of 2-Oxopurine Derivatives as Potential HIV Reverse Transcriptase Inhibitors.
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Bakkestuen, Anne Kristin Vibstad; Gundersen, Lise-Lotte & Rise, Frode
(2001).
Synthetic Studies towards Trixagol and Agelasine E.
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Teklu, Solomon; Gundersen, Lise-Lotte; Rise, Frode; Østby, Ole Benny & Malterud, Karl Egil
(2001).
Radical scavenging properties of indolizine derivatives.
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Bråthe, Anders; Gundersen, Lise-Lotte; Rise, Frode & Malterud, Karl Egil
(2001).
Antioxidant properties of some cytokinin analogues.
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Bråthe, Anders; Gundersen, Lise-Lotte; Rise, Frode & Malterud, Karl Egil
(2001).
Antioxidant properties of some cytokinin analogues.
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Spilsberg, Bjørn; Rise, Frode; Petersen, Dirk & Nissen-Meyer, Jon
(2000).
SECRETION OF THYMIDINE BY HYBRIDOMA CELLS.
Show summary
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.
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Østby, Ole Benny; Gundersen, Lise-Lotte & Rise, Frode
(2000).
Synthesis of 1-Substituted 7-Cyano-2,3-diphenylindolizines as Potential Antioxidants.
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Andresen, Geir; Gundersen, Lise-Lotte & Rise, Frode
(2000).
Synthesis of 6-Substituted 2-Oxopurines as Potential Plant Hormones.
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Østby, Ole Benny; Rise, Frode & Gundersen, Lise-Lotte
(2000).
Assignment of 13C Resonances of Indolizines Using Optimised COLOC, HMBC and INADEQUATE NMR.
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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.
Show summary
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.
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Netland, Kjetil Andreas; Gundersen, Lise-Lotte & Rise, Frode
(2000).
An improved Synthesis of Dialkylcyclopropenones.
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Netland, Kjetil Andreas; Gundersen, Lise-Lotte & Rise, Frode
(2000).
13C Assignment of Cyclopropenone Resonances.
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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.
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Rise, Frode
(1999).
A Different Kind of Lecture.
Show summary
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
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Øverås, Anniken Thomsen; Gundersen, Lise-Lotte & Rise, Frode
(1998).
Nucleophilic Addition and Diels-Alder Reactions on 6-Vinylpurines.
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Bråthe, Anders; Gundersen, Lise-Lotte; Rise, Frode; Eriksen, Aud Else Berglen & Wang, Linnea
(1998).
Synthesis of Cytokinin Analogues.
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Nolsøe, Jens M. J.; Rise, Frode & Gundersen, Lise-Lotte
(1998).
Synthesis of 6,8-Dihalopurines and Studies of their Reactivity in Cross Coupling Reactions.
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Nasir, Achmad I.; Gundersen, Lise-Lotte; Rise, Frode; Bast, Aalt & Haenen, Guido R. M. M.
(1997).
Syntese av indolisiner med antioksidant egenskaper.
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Nolsøe, Jens M. J.; Rise, Frode & Gundersen, Lise-Lotte
(1997).
Regiokjemiske studier av kobling mellom 6,8-dihalopuriner og organometalliske reagenser.
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Bråthe, Anders; Rise, Frode & Gundersen, Lise-Lotte
(1997).
Heck koblinger på vinylpurin; syntese av potensielle cytokininer.
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Andresen, Geir; Gundersen, Lise-Lotte & Rise, Frode
(1996).
Regioselektiv C-C bindingsdannelse på benzylerte 2-oksopuriner.
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Gundersen, Lise-Lotte; Langli, Geir; Rise, Frode & Thomsen, Anniken
(1996).
Pd-Catalyzed C-C Bond Formation in Purines.
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Thomsen, Anniken; Gundersen, Lise-Lotte & Rise, Frode
(1996).
Nukleofile addisjoner og sykloaddisjoner til 6-vinylpuriner.
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Langli, Geir; Gundersen, Lise-Lotte & Rise, Frode
(1996).
2,6-Dihalopuriner i regioselektive palladiumkatalyserte koblinger med organotinnreagenser.
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Andresen, Geir; Gundersen, Lise-Lotte & Rise, Frode
(1996).
Regioselective Addition of Grignard Reagents to 2-Purinone Derivatives.
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Andresen, Geir; Gundersen, Lise-Lotte & Rise, Frode
(1995).
Structure Determination of 2-Oxopurine Derivatives with NMR.
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Gundersen, Lise-Lotte; Langli, Geir; Rise, Frode & Øverås, Harald
(1995).
Strategier for karbon - karbon bindingsdannelse i puriner.
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Øverås, Harald; Gundersen, Lise-Lotte; Rise, Frode & Aasen, Arne Jørgen
(1995).
6-Halopuriner i palladium-katalyserte koblinger med organosink reagenser.
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Langli, Geir; Gundersen, Lise-Lotte & Rise, Frode
(1995).
2,6-Diklorpuriner i Palladium-katalyserte koblinger med organotinn og organosink reagenser.
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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.
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Ugland, Sigurd; Gundersen, Lise-Lotte; Rise, Frode; Bast, Aalt & Haenen, Guido R. M. M.
(1995).
Syntese av potensielle antioksidanter og nevrobeskyttende forbindelser.
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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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Mallia, Vittoria; Uhlig, Silvio; Miles, Christopher Owen; Eriksen, Gunnar Sundstøl; Sandvik, Morten & Rise, Frode
(2020).
Potential endocrine disrupting activity of cyanobacteria – possible roles for microcystins.
Matematisk Naturvitenskapelig fakultet, Universitetet i Oslo.
ISSN 1501-7710.
2020(2317).
Show summary
This thesis investigated the connection between two major global concerns: the infamous cyanobacteria (“blue-green algae”), and the endocrine disruptors, compounds able to interfere with the hormonal system.
Do cyanobacteria exert endocrine disrupting activity? Are the cyanobacterial toxins “microcystins” involved?
Cyanobacterial extracts, complex combinations of known and unknown compounds including microcystins, were screened using specific in vitro assays to assess their potential endocrine activity. Pure microcystins were also tested. Results showed that cyanobacterial compounds (microcystins, but also other metabolites) could have an endocrine disrupting activity, especially interfering with hormone production and metabolism. Furthermore, a combination of chemical analysis and reactions were used to deepen structural knowledge of microcystins (they are a family including hundreds of congeners!). Seven new microcystin congeners were identified in this work.
Resulting data on the endocrine activity of cyanobacteria as well as the discovery of new microcystins highlighted the complexity and the many “unknowns” that remain behind these two global concerns and their interconnection.
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Cordero, Patricia Reyes; Rise, Frode & Hassel, Bjørnar
(2020).
NMR and spectrophotometric investigations of D-glyceraldehyde metabolism via methylglyoxal.
Universitetet i Oslo.
Show summary
Aldehydes are toxic carbonylcompoundsthatcanreact with proteins and modify theirfunction, stability and shape, e.g by inducing AGEs production. This class of compounds can be formed intracellularly and can betransported to the extracellular environment. D-glyceraldehyde, a hydroxyaldehyde, can cross thecellmembrane,but the transport mechanism has notyetbeenfullyelucidated.Transport of D-GA across a cell membrane has been studied in isolated nerve terminals from the formation of D-lactate, which is recovered in the extracellular fluid, and the specificity of the aldehyde transport mechanism has been studied by the inhibitory effect of other aldehydes on D-lactate formation from D-GA. However, it is not known whether other aldehydes inhibit the D-GA transport mechanism or if they inhibit the enzymatic reactionsleading from D-GA to D-lactate.The objective of this investigation was to study the enzymatic pathway from D-GA to D-lactate and the effect of differentaldehydes on the enzyme activities in this pathway.By identifying aldehydes that do not inhibit these enzymes, one can more safely assume that they are pure inhibitors of the aldehyde transport mechanism in the cell membrane.The competing aldehydes were acetaldehyde, acrolein, butanal, crotonaldehyde, formaldehyde, L-glyceraldehyde,methylglyoxal and propanal. Another objective was to evaluate the fibrillation of the protein glucagon by various aldehydes. Nuclear magnetic resonance (NMR)spectroscopyand UV spectrophotometry were used to study enzymatic reactions involved in D-GA metabolism. Liquid-state 1H NMR was used to investigate if aldehydes induced fibrillation of glucagon, a protein that readily undergoes fibrillation.The aldehydes that inhibited the phosphorylation of D-glyceraldehyde or the glyoxalase system werebutanal, formaldehyde, methylglyoxaland L-glyceraldehyde. Aldehydes that did not inhibit these enzymes wereacetaldehyde, acrolein, crotonaldehyde and propanal.The latter aldehydes are probably inhibitors of the aldehyde transport mechanism in the cell membrane. None of the aldehydes seemed to initiate the fibrillogenesisof glucagon.
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Racz, Beatrix; Wilson, Steven Ray Haakon; Rise, Frode & Lundanes, Elsa
(2018).
Identification of a major UV absorbing compound in goose aqueous humour.
Universitetet i Oslo.
Show summary
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.
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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.
Universitetet i Oslo.
Show summary
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.
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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.
Unipub forlag.
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Bråthe, Anders; Gundersen, Lise-Lotte & Rise, Frode
(2004).
Synthesis of purine derivatives with plant growth, antioxidant and cytotoxic properties.
Unipub forlag.
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Teklu, Solomon; Gundersen, Lise-Lotte & Rise, Frode
(2004).
Synthesis, biological activities and electrochemical studies of indolizine derivatives.
Unipub forlag.
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Negussie, Ayele Hailu; Gundersen, Lise-Lotte & Rise, Frode
(2004).
Synthesis of indolizine derivatives and screening of their antimycobacterial and 15-LO activity.
7Letras.
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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.
7Letras.
ISSN 82-996093-0-5.
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Andresen, Geir; Gundersen, Lise-Lotte & Rise, Frode
(2001).
Syntheses towards biologically active 2-oxopurine derivatives.
Unipub forlag.
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Østby, Ole Benny; Gundersen, Lise-Lotte & Rise, Frode
(2001).
Syntese av 1-substituerte ondoliziner som potensielle antioksidanter.
7Letras.
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Netland, Kjetil Andreas; Gundersen, Lise-Lotte & Rise, Frode
(2000).
Syntese av syklopropenoner.
7Letras.
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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.
7Letras.
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Bråthe, Anders; Gundersen, Lise-Lotte & Rise, Frode
(1998).
Syntese av cytokininanaloger.
7Letras.
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Nasir, Achmad Izzudin; Gundersen, Lise-Lotte & Rise, Frode
(1997).
Syntese av syklopropenoner og indoliziner med antioksidantegenskaper.
7Letras.
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Øverås, Anniken Thomsen; Gundersen, Lise-Lotte & Rise, Frode
(1997).
Diels-Alder- og addisjonsreaksjoner på 6-vinylpuriner.
7Letras.
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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.
7Letras.
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Langli, Geir; Gundersen, Lise-Lotte & Rise, Frode
(1996).
Regioselektive palladiumkatalyserte koblinger mellom 2,6-dihalopuriner og organometaller.
7Letras.
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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.
7Letras.
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Bakkestuen, Anne Kristin; Gundersen, Lise-Lotte; Rise, Frode & Aasen, Arne Jørgen
(1994).
Palladiumkatalyserte koblingsreaksjoner mellom tetraorganotinnforbindelser og N-benzylert 6-klorpurin.
7Letras.