Studies of the biosynthesis of DTX-5a and DTX-5b by the Dinoflagellate Prorocentrum maculosum : regiospecificity of the putative Baeyer−Villigerase and insertion of a single Amino Acid in a Polyketide chain

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DOIResolve DOI: http://doi.org/10.1021/jo0204754
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TypeArticle
Journal titleThe Journal of Organic Chemistry
ISSN0022-3263
1520-6904
Volume68
Issue5
Pages16591664; # of pages: 6
Subjectamino acid; dinophysistoxin 1; dinophysistoxin 5a; dinophysistoxin 5b; glycine; oxygen; polyketide; unclassified drug
AbstractThe biosynthetic origins of the diarrhetic shellfish poisoning toxins DTX-5a and DTX-5b have been elucidated by supplementing cultures of the producing organism Prorocentrum maculosum with stable isotope labeled precursors and determining the incorporation patterns by 13C NMR spectroscopy. The amino acid residue in the sulfated side chain is found to originate from glycine, and oxygen insertion in the chain is shown to occur after polyketide formation.
Publication date
PublisherACS Publications
LanguageEnglish
AffiliationNational Research Council Canada; NRC Institute for Marine Biosciences
Peer reviewedYes
NRC number42372
NPARC number21271014
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Record identifierc08a8464-3bd6-42b5-ab4b-84bd729f6dee
Record created2014-03-12
Record modified2016-05-09
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