Biosynthesis of 13-Desmethyl Spirolide C by the dinoflagellate Alexandrium ostenfeldii

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DOIResolve DOI: http://doi.org/10.1021/jo0608873
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TypeArticle
Journal titleJournal of Organic Chemistry
Volume71
Issue23
Pages87248731; # of pages: 8
AbstractBiosynthetic origins of the cyclic imine toxin 13-desmethyl spirolide C were determined by supplementing cultures of the toxigenic dinoflagellate Alexandrium ostenfeldii with stable isotope-labeled precursors [1,2-13C2]acetate, [1-13C]acetate, [2-13CD3]acetate, and [1,2-13C2,15N]glycine and measuring the incorporation patterns by 13C NMR spectroscopy. Despite partial scrambling of the acetate labels, the results show that most carbons of the macrocycle are polyketide-derived and that glycine is incorporated as an intact unit into the cyclic imine moiety. This work represents the first conclusive evidence that such cyclic imine toxins are polyketides and provides support for biosynthetic pathways previously defined for other polyether dinoflagellate toxins.
Publication date
PublisherACS Publications
Copyright notice2006 American Chemistry Society
LanguageEnglish
AffiliationNRC Institute for Marine Biosciences; National Research Council Canada; Aquatic and Crop Resource Development; Measurement Science and Standards
Peer reviewedYes
IdentifierNRC-ACRD-55892
NRC number1560
NPARC number3538225
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Record identifier6fbbf39a-f5c1-4dda-819d-46864e0c9b80
Record created2009-03-01
Record modified2016-05-09
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