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Production of 3,4-cis- and 3,4-trans-Leucocyanidin and Their Distinct MS/MS Fragmentation Patterns

dc.rights.licenseopenen_US
dc.relation.isnodouble8b56323d-95cf-4a3d-b7e7-1578f0fcaafc*
hal.structure.identifierChimie et Biologie des Membranes et des Nanoobjets [CBMN]
dc.contributor.authorZHANG, Jia-Rong
hal.structure.identifierChimie et Biologie des Membranes et des Nanoobjets [CBMN]
dc.contributor.authorTOLCHARD, James
hal.structure.identifierChimie et Biologie des Membranes et des Nanoobjets [CBMN]
dc.contributor.authorBATHANY, Katell
hal.structure.identifierChimie et Biologie des Membranes et des Nanoobjets [CBMN]
dc.contributor.authorD'ESTAINTOT, Beatrice Langlois
hal.structure.identifierChimie et Biologie des Membranes et des Nanoobjets [CBMN]
dc.contributor.authorCHAUDIERE, Jean
dc.date.accessioned2020-04-07T16:02:16Z
dc.date.available2020-04-07T16:02:16Z
dc.date.issued2018
dc.identifier.issn0021-8561en_US
dc.identifier.other10.1021/acs.jafc.7b04380en_US
dc.identifier.urihttps://oskar-bordeaux.fr/handle/20.500.12278/4155
dc.description.abstractEn(+)-2,3-trans-3,4-cis-Leucocyanidin was produced by acidic epimerization of (+)-2,3-trans-3,4-trans-leucocyanidin synthesized by reduction of (+)-dihydroquercetin with NaBH4, and structures of the two stereoisomers purified by C18- and phenyl-reverse-phase high-performance liquid chromatography (HPLC) were confirmed by NMR spectroscopy. We confirm that only 3,4-cis-leucocyanidin is used by leucoanthocyanidin reductase as substrate. The two stereoisomers are quite stable in aqueous solution at -20 degrees C. Characterization of the two stereoisomers was also performed using electrospray ionization tandem mass spectrometry (ESI-MS/MS), and we discuss here for the first time the corresponding MS/MS fragmentation pathways, which are clearly distinct. The main difference is that of the mode of dehydration of the 3,4-diol in positive ionization mode, which involves a loss of hydroxyl group at either C-3 or C-4 for the 3,4-cis isomer but only at C-3 for the 3,4-trans isomer. Tandem mass spectrometry therefore proves useful as a complementary methodology to NMR to identify each of the two stereoisomers.
dc.language.isoENen_US
dc.subject.enLeucocyanidin
dc.subject.enNMR
dc.subject.enleucoanthocyanidin reductase
dc.subject.enreverse-phase HPLC
dc.subject.entandem mass spectrometry
dc.subject.enfragmentation pathways
dc.title.enProduction of 3,4-cis- and 3,4-trans-Leucocyanidin and Their Distinct MS/MS Fragmentation Patterns
dc.title.alternativeJ. Agric. Food Chem.en_US
dc.typeArticle de revueen_US
dc.identifier.doi10.1021/acs.jafc.7b04380
dc.subject.halChimie/Matériauxen_US
bordeaux.journalJournal of Agricultural and Food Chemistryen_US
bordeaux.page351-358en_US
bordeaux.volume66en_US
bordeaux.hal.laboratoriesInstitut de Chimie & de Biologie des Membranes & des Nano-objets (CBMN) - UMR 5248
bordeaux.issue1en_US
bordeaux.institutionBordeaux INPen_US
bordeaux.institutionUniversité de Bordeauxen_US
bordeaux.peerReviewedouien_US
bordeaux.inpressnonen_US
hal.identifierhal-03160315
hal.version1
hal.date.transferred2021-03-05T09:09:47Z
hal.exporttrue
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