Biosynthesis of antibiotic 1233A (F-244) and preparation of [14C]1233A

J Antibiot (Tokyo). 1992 Apr;45(4):563-7. doi: 10.7164/antibiotics.45.563.

Abstract

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).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetates / metabolism
  • Anti-Bacterial Agents / biosynthesis*
  • Anti-Bacterial Agents / chemical synthesis
  • Carbon Isotopes
  • Carbon Radioisotopes
  • Chromatography, High Pressure Liquid
  • Fatty Acids, Unsaturated / biosynthesis*
  • Fatty Acids, Unsaturated / chemical synthesis
  • Hydroxymethylglutaryl-CoA Synthase / antagonists & inhibitors*
  • Lactones / chemical synthesis
  • Lactones / metabolism
  • Magnetic Resonance Spectroscopy
  • Methionine / metabolism
  • Microbiological Techniques
  • Mitosporic Fungi / metabolism

Substances

  • Acetates
  • Anti-Bacterial Agents
  • Carbon Isotopes
  • Carbon Radioisotopes
  • Fatty Acids, Unsaturated
  • Lactones
  • antibiotic 1233A
  • Methionine
  • Hydroxymethylglutaryl-CoA Synthase