Evidence for the combined participation of a C10 and a C15 precursor in the biosynthesis of moenocinol, the lipid part of the moenomycin antibiotics

Chembiochem. 2003 Nov 7;4(11):1201-5. doi: 10.1002/cbic.200300622.

Abstract

Upon feeding of [2-(13)C,4-(2)H]-1-deoxy-D-xylulose to Streptomyces ghanaensis, the deuterium label was retained exclusively at positions C-7 and C-17 in the moenocinol part of the moenomycin antibiotics. This result vindicates the hypothesis that the C(25) structure of moenocinol is assembled from a C(10) and a C(15) precursor, each of which requires for its formation the involvement of a dimethylallyl diphosphate starter unit.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / biosynthesis*
  • Anti-Bacterial Agents / chemistry
  • Hemiterpenes / chemistry
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Oligosaccharides / biosynthesis*
  • Oligosaccharides / chemistry
  • Organophosphorus Compounds / chemistry
  • Streptomyces / metabolism*
  • Terpenes / blood*
  • Terpenes / chemistry
  • Xylulose / analogs & derivatives*
  • Xylulose / metabolism

Substances

  • Anti-Bacterial Agents
  • Hemiterpenes
  • Oligosaccharides
  • Organophosphorus Compounds
  • Terpenes
  • moenocinol
  • isopentenyl pyrophosphate
  • 3,3-dimethylallyl pyrophosphate
  • Xylulose
  • 1-deoxy-2-pentulose
  • moenomycin