Cepacidine A, a novel antifungal antibiotic produced by Pseudomonas cepacia. II. Physico-chemical properties and structure elucidation

J Antibiot (Tokyo). 1994 Dec;47(12):1406-16. doi: 10.7164/antibiotics.47.1406.

Abstract

Cepacidine A is a novel glycopeptide with a potent antifungal activity, which is produced by Pseudomonas cepacia AF 2001. Its molecular weight was determined by FAB-MS (m/z 1215). The compound is comprised of glycine (1), serine (2), 2,4-diaminobutyric acid (1), aspartic acid (1), beta-hydroxy tyrosine (1), beta-hydroxy asparagine (1), xylose (1) and 5,7-dihydroxy-3,9-diamino-octadecanoic acid (1). Unfortunately, cepacidine A is a mixture of A1 and A2, either of which is barely distinguishable. Cepacidine A2 includes asparagine (1) instead of beta-hydroxy asparagine (1) of cepacidine A1. The MS data and the NOESY, TOCSY and HMBC spectra show that cepacidine A is a cyclic peptide and xylose is connected to 5,7-dihydroxy-3,9-diaminooctadecanoic acid.

MeSH terms

  • Anti-Bacterial Agents / chemistry*
  • Antifungal Agents / chemistry*
  • Burkholderia cepacia / metabolism*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Peptides*
  • Spectrometry, Mass, Fast Atom Bombardment

Substances

  • Anti-Bacterial Agents
  • Antifungal Agents
  • Peptides
  • cepacidine A