Biosynthesis of antibiotic 1233A (F-244) and preparation of [14C]1233A.
The biosynthesis of antibiotic 1233A (F-244) was studied by feeding 13C-labeled precursors to the producing organism, Scopulariopsis sp. F-244. 13C NMR spectroscopy established that 1233A is derived from 4 methionines and 7 acetates. Seven acetates are condensed to form a hexaketide and 4 methyl residues from methionine are introduced into the main skeleton. The beta-lactone is derived from the alpha-carboxylic acid of the hexaketide. Since methionine was efficiently incorporated into 1233A, radiolabeled 1233A was prepared biosynthetically by feeding [14C]methionine to the producer. As a result, [14C]1233A was obtained with high specific radioactivity (27.2 muCi/mumols).
Kumagai
H
H
Research Center for Biological Function, Kitasato Institute, Tokyo, Japan.
Tomoda
H
H
Omura
S
S
D000085:Acetates / Q000378:metabolism; D000900:Anti-Bacterial Agents / Q000096:biosynthesis* / Q000138:chemical synthesis; D002247:Carbon Isotopes; D002250:Carbon Radioisotopes; D002851:Chromatography, High Pressure Liquid; D005231:Fatty Acids, Unsaturated / Q000096:biosynthesis* / Q000138:chemical synthesis; D006904:Hydroxymethylglutaryl-CoA Synthase / Q000037:antagonists & inhibitors*; D007783:Lactones / Q000138:chemical synthesis / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D008715:Methionine / Q000378:metabolism; D008828:Microbiological Techniques; D003904:Mitosporic Fungi / Q000378:metabolism
D000085:Acetates; D000900:Anti-Bacterial Agents; D002247:Carbon Isotopes; D002250:Carbon Radioisotopes; D005231:Fatty Acids, Unsaturated; D007783:Lactones; C054282:antibiotic 1233A; D008715:Methionine; D006904:Hydroxymethylglutaryl-CoA Synthase