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dc.contributor.authorStevenson, David E.
dc.contributor.authorHansen, Richard P.
dc.contributor.authorLoader, Jared I.
dc.contributor.authorJensen, Dwayne J.
dc.contributor.authorCooney, Janine M.
dc.contributor.authorWilkins, Alistair L.
dc.contributor.authorMiles, Christopher O.
dc.date.accessioned2009-08-17T22:57:35Z
dc.date.available2009-08-17T22:57:35Z
dc.date.issued2008
dc.identifier.citationStevenson, D. E., Hensen, R. P., Loader, J. I., et al. (2008). Preparative enzymatic synthesis of glucuronides of zearalenone and five of its metabolites. Journal of Agricultural and Food Chemistry. 56(11), 4032-4038.en
dc.identifier.urihttps://hdl.handle.net/10289/2839
dc.description.abstractThe resorcylic acid lactones zearalenone (1), α-zearalenol (2), β-zearalenol (3), α-zearalanol (zeranol) (4), β-zearalanol (taleranol) (5), and zearalanone (6) were converted to their glucuronides on a preparative scale in good yields. Reactions were conducted with bovine uridine 5′-diphosphoglucuronyl transferase (UDPGT) as catalyst and uridine 5′-diphosphoglucuronic acid (UDPGA) as cofactor. The glucuronides were isolated by column chromatography and characterized by NMR spectroscopy and mass spectrometry. Although the principal products were 4-O-glucuronides (i.e., linkage through a phenolic hydroxyl), significant quantities of the 6′-O-glucuronides (i.e., linkage through the aliphatic hydroxyl) of alcohols 2, 4, and 5 were also isolated. In the case of 3, the 2-O-glucuronide was isolated as the minor product. Overall isolated yields of glucuronides, performed on a 20−50 mg scale, were typically ca. 80% based on the resorcylic acid lactone starting material. LC-UV-MS2 analysis of purified specimens revealed MS2 fragmentations useful for defining the point of attachment of the glucuronide moiety to the zearalenone nucleus.en
dc.language.isoen
dc.publisherAmerican Chemical Societyen_NZ
dc.relation.urihttp://pubs.acs.org/doi/abs/10.1021/jf800379zen
dc.subjectchemistryen
dc.titlePreparative enzymatic synthesis of glucuronides of zearalenone and five of its metabolitesen
dc.typeJournal Articleen
dc.identifier.doi10.1021/jf800379zen
dc.relation.isPartOfJournal of Agricultural and Food Chemistryen_NZ
pubs.begin-page4032en_NZ
pubs.elements-id34264
pubs.end-page4038en_NZ
pubs.issue11en_NZ
pubs.volume56en_NZ


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