NMR analysis of quinocycline antibiotics: structure determination of kosinostatin, an antitumor substance from Micromonospora sp. TP-A0468

J Antibiot (Tokyo). 2002 Feb;55(2):134-40. doi: 10.7164/antibiotics.55.134.

Abstract

A quinocycline antibiotic, kosinostatin, was isolated from the culture broth of Micromonospora sp. TP-A0468 along with isoquinocycline B. Structure of kosinostatin was determined to be the stereoisomer of isoquinocycline B regarding to the stereochemistry at the C-2' spiro carbon by NMR analysis. Kosinostatin isomerizes to isoquinocycline B through the inversion of the stereocenter at C-2'. Comparison of physico-chemical properties indicated that kosinostatin is presumably identical with quinocycline B isolated by CELMER et al. from Streptomyces aureofaciens.

MeSH terms

  • Aminoglycosides*
  • Anti-Bacterial Agents / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Stereoisomerism

Substances

  • Aminoglycosides
  • Anti-Bacterial Agents
  • kosinostatin