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dc.date.accessioned2017-12-19T11:50:39Z
dc.date.available2017-12-19T11:50:39Z
dc.date.created2016-10-05T21:43:33Z
dc.date.issued2016
dc.identifier.citationPrimdahl, Karoline Gangestad Aursnes, Marius Walker, Mary E. Colas, Romain A. Serhan, Charles N. Dalli, Jesmond Hansen, Trond Vidar Vik, Anders . Synthesis of 13(R)‐Hydroxy‐7Z,10Z,13R,14E,16Z,19Z Docosapentaenoic Acid (13R‐HDPA) and Its Biosynthetic Conversion to the 13-Series Resolvins. Journal of natural products. 2016, 79, 2693-2702
dc.identifier.urihttp://hdl.handle.net/10852/59382
dc.description.abstractSpecialized pro-resolving lipid mediators are biosynthesized during the resolution phase of acute inflammation from n-3 polyunsaturated fatty acids. Recently, the isolation and identification of the four novel mediators denoted 13-series resolvins, namely, RvT1 (1), RvT2 (2), RvT3 (3) and RvT4 (4), were reported, which showed potent bioactions characteristic for specialized pro-resolving lipid mediators. Herein, based on results from LC/MS-MS metabololipidomics and the stereoselective synthesis of 13(R)-hydroxy-7Z,10Z,13R,14E,16Z,19Z docosapentaenoic acid (13R-HDPA, 5), we provide direct evidence that the four novel mediators 1−4 are all biosynthesized from the pivotal intermediate 5. The UV and LC/MS-MS results from synthetic 13R-HDPA (5) matched those from endogenously and biosynthetically produced material obtained from in vivo infectious exudates, endothelial cells, and human recombinant COX-2 enzyme. Stereochemically pure 5 was obtained with the use of a chiral pool starting material that installed the configuration at the C-13 atom as R. Two stereoselective Z-Wittig reactions and two Z-selective reductions of internal alkynes afforded the geometrically pure alkene moieties in 5. Incubation of 5 with isolated human neutrophils gave all four RvTs. The results presented herein provide new knowledge on the biosynthetic pathways and the enzymatic origin of RvTs 1−4.en_US
dc.languageEN
dc.language.isoenen_US
dc.relation.ispartofKaroline Gangestad Primdahl (2017) Stereoselective Syntheses of Oxygenated Polyunsaturated Fatty Acid Mediators and Investigations of Biosynthetic Pathways. Doctoral thesis http://urn.nb.no/URN:NBN:no-61836
dc.relation.urihttp://urn.nb.no/URN:NBN:no-61836
dc.rightsAttribution 4.0 International
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/
dc.titleSynthesis of 13(R)‐Hydroxy‐7Z,10Z,13R,14E,16Z,19Z Docosapentaenoic Acid (13R‐HDPA) and Its Biosynthetic Conversion to the 13-Series Resolvinsen_US
dc.typeJournal articleen_US
dc.creator.authorPrimdahl, Karoline Gangestad
dc.creator.authorAursnes, Marius
dc.creator.authorWalker, Mary E.
dc.creator.authorColas, Romain A.
dc.creator.authorSerhan, Charles N.
dc.creator.authorDalli, Jesmond
dc.creator.authorHansen, Trond Vidar
dc.creator.authorVik, Anders
cristin.unitcode185,15,23,20
cristin.unitnameFarmasøytisk kjemi
cristin.ispublishedtrue
cristin.fulltextoriginal
cristin.qualitycode2
dc.identifier.cristin1389792
dc.identifier.bibliographiccitationinfo:ofi/fmt:kev:mtx:ctx&ctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.jtitle=Journal of natural products&rft.volume=79&rft.spage=2693&rft.date=2016
dc.identifier.jtitleJournal of natural products
dc.identifier.volume79
dc.identifier.startpage2693
dc.identifier.endpage2702
dc.identifier.doihttp://dx.doi.org/10.1021/acs.jnatprod.6b00634
dc.identifier.urnURN:NBN:no-62068
dc.subject.nviVDP::Organisk kjemi: 441
dc.type.documentTidsskriftartikkelen_US
dc.type.peerreviewedPeer reviewed
dc.source.issn0163-3864
dc.identifier.fulltextFulltext https://www.duo.uio.no/bitstream/handle/10852/59382/1/acs-jnatprod-6b00634.pdf
dc.type.versionPublishedVersion
dc.relation.projectNFR/230470


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