Antibiotics A21459 A and B, new inhibitors of bacterial protein synthesis. II. Structure elucidation

J Antibiot (Tokyo). 1996 Feb;49(2):150-4. doi: 10.7164/antibiotics.49.150.

Abstract

The structures of the antibiotics, active against a few Gram-negative bacteria and Clostridium difficile, were determined on the basis of physicochemical analyses on the intact molecules and on the acid hydrolysate of A21459 A. FAB-MS and 1H and 13C NMR investigations identified the amino acid units and determined their sequence. Antibiotics A21459 A and B are homodetic cyclic peptides constituted by eight amino acid units. They are glycine, methoxytryptophan, tryptophan, cysteine, alanine, sarcosine, dehydroalanine, and alpha-aminobutyric acid for A21459 A (alanine for A21459 B). Cysteine and alanine condensed to form a thiazole moiety, according to the biosynthesis of thiazole containing antibiotics.

MeSH terms

  • Amino Acid Sequence
  • Amino Acids / analysis
  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / pharmacology
  • Peptides, Cyclic / chemistry
  • Peptides, Cyclic / pharmacology
  • Spectrum Analysis

Substances

  • A21459 A
  • A21459 B
  • Amino Acids
  • Anti-Bacterial Agents
  • Peptides, Cyclic