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.
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.
Macpherson
Gordon R
GR
Institute for Marine Biosciences, National Research Council of Canada, 1411 Oxford Street, Halifax, Nova Scotia, Canada B3H 3Z1.
Burton
Ian W
IW
LeBlanc
Patricia
P
Walter
John A
JA
Wright
Jeffrey L C
JL
D000596:Amino Acids / Q000737:chemistry; D000818:Animals; D002247:Carbon Isotopes; D002384:Catalysis; D002853:Chromatography, Liquid; D004141:Dinoflagellida / Q000737:chemistry*; D005998:Glycine / Q000737:chemistry; D008387:Marine Toxins / Q000096:biosynthesis / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism / Q000494:pharmacology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D019319:Okadaic Acid / Q000737:chemistry / Q000031:analogs & derivatives
D000596:Amino Acids; D002247:Carbon Isotopes; D008387:Marine Toxins; C114941:dinophysistoxin 5; C114940:dinophysistoxin 4; D019319:Okadaic Acid; D005998:Glycine