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 | Zendy

Gordon R. Macpherson | Zendy; Ian W. Burton | Zendy; Patricia LeBlanc | Zendy; John A. Walter | Zendy; Jeffrey L. C. Wright | Zendy

Open Access

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

Author(s) -

Gordon R. Macpherson,

Ian W. Burton,

Patricia LeBlanc,

John A. Walter,

Jeffrey L. C. Wright

Publication year - 2002

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/jo0204754

Subject(s) - dinoflagellate , biosynthesis , polyketide , stereochemistry , residue (chemistry) , chemistry , glycine , biochemistry , amino acid , biology , botany , gene

The 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.

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