Structure of bacillomycin F, a new peptidolipid antibiotic of the iturin group

Eur J Biochem. 1985 Dec 2;153(2):335-40. doi: 10.1111/j.1432-1033.1985.tb09307.x.

Abstract

The structure of a new antibiotic of the iturin group, bacillomycin F, has been demonstrated. It is a mixture of homologous peptidolipids, essentially C51H80N12O14 and C52N82N12O14. The lipid moiety consists of minor isoC15, anteisoC15 beta-amino acids and major isoC16, isoC17 and anteisoC17 beta-amino acids. The peptide sequence was determined by studying the peptides obtained after mild HCl hydrolysis and by Edman degradation of bacillomycin F treated with N-bromosuccinimide. The sequence was confirmed by two-dimensional NMR spectrometry and fast-atom-bombardment mass spectrometry gave the molecular masses of the homologous compounds. Bacillomycin F is a cyclic peptidolipid; its complete structure is given in the paper.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Amino Acids / analysis
  • Anti-Bacterial Agents / analysis*
  • Chemical Phenomena
  • Chemistry
  • Chromatography / methods
  • Chromatography, High Pressure Liquid
  • Lipids / analysis
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Peptides, Cyclic / analysis
  • Solubility
  • Water

Substances

  • Amino Acids
  • Anti-Bacterial Agents
  • Lipids
  • Peptides, Cyclic
  • Water
  • bacillomycin F