Metabolic products of microorganisms. 258. Enzymatic bromination of nikkomycin Z

J Antibiot (Tokyo). 1991 Jun;44(6):626-34. doi: 10.7164/antibiotics.44.626.

Abstract

Two brominated nikkomycins were produced by enzymatic halogenation of nikkomycin Z in the presence of a nonheme bromoperoxidase isolated from Streptomyces aureofaciens Tü 24. The monobrominated and dibrominated nikkomycin Z derivatives were substituted at the hydroxypyridyl moiety of the N-terminal amino acid of nikkomycin Z at position C-6"' (ZBr) or C-4"' and C-6"' (ZBr2). The brominated nikkomycin Z derivatives had a decreased affinity to chitin synthase of Coprinus cinereus as compared to nikkomycin Z and exhibited a low inhibitory activity towards various fungi and yeasts.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aminoglycosides*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / metabolism*
  • Anti-Bacterial Agents / pharmacology
  • Antifungal Agents / metabolism*
  • Bacteria / drug effects
  • Chitin Synthase / metabolism
  • Chromatography, High Pressure Liquid
  • Cloning, Molecular
  • Coprinus / enzymology
  • Gene Expression Regulation, Bacterial
  • Gene Expression Regulation, Enzymologic
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Molecular Structure
  • Peroxidases / genetics
  • Peroxidases / metabolism*
  • Plasmids
  • Saccharomyces cerevisiae / drug effects
  • Spectrophotometry, Ultraviolet
  • Streptomyces / genetics
  • Streptomyces aureofaciens / enzymology*
  • Transformation, Bacterial

Substances

  • Aminoglycosides
  • Anti-Bacterial Agents
  • Antifungal Agents
  • nikkomycin
  • Peroxidases
  • bromide peroxidase
  • Chitin Synthase