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

• Published in: Journal of organic chemistry Vol. 68; no. 5; pp. 1659 - 1664
• Main Authors: MACPHERSON, Gordon R., BURTON, Ian W., LEBLANC, Patricia, WALTER, John A., WRIGHT, Jeffrey L. C.
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 07.03.2003; Amer Chemical Soc
• Subjects: Amino Acids - chemistry; Animals; Bioconversions. Hemisynthesis; Biological and medical sciences; Biotechnology; Carbon Isotopes; Catalysis; Chemistry; Chemistry, Organic; Chromatography, Liquid; Dinoflagellida - chemistry; Fundamental and applied biological sciences. Psychology; Glycine - chemistry; Marine Toxins - biosynthesis; Marine Toxins - chemistry; Marine Toxins - isolation & purification; Marine Toxins - metabolism; Marine Toxins - pharmacology; Methods. Procedures. Technologies; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Okadaic Acid - chemistry; Physical Sciences; Science & Technology; LIMA; MICROCYSTIN; ORIGIN; DINOPHYSISTOXIN-1; GENE-CLUSTER; POLYETHER; TOXINS; OKADAIC ACID; PEPTIDE SYNTHETASE; Polyketide; Baeyer Villiger reaction; Isotope labelling; Enzyme; Aminoacid; Biosynthesis; NMR spectrometry; Regiospecificity
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo0204754

The biosynthetic origins of the diarrhetic shellfish poisoning toxin 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 C-13 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.