Tetrodecamycin and dihydrotetrodecamycin, new antimicrobial antibiotics against Pasteurella piscicida produced by Streptomyces nashvillensis MJ885-mF8. II. Structure determination

J Antibiot (Tokyo). 1995 Oct;48(10):1110-4. doi: 10.7164/antibiotics.48.1110.

Abstract

Novel antimicrobial antibiotics against Pasteurella piscicida, tetrodecamycin (1) and weakly active dihydrotetrodecamycin (2) were isolated from a culture broth of Streptomyces nashvillensis MJ885-mF8. The planar structure of 1 was determined to be 2-acyl-4-ylidene tetronic acid alkyl ether containing decaline ring by various NMR spectral data of 1 and its acetyl derivative (3). The structure of 2 was elucidated by comparison with the spectral data of 1 and confirmed by catalytic reduction of 1 into 2. The X-ray crystallography of 2 showed the relative stereochemistry. Their absolute configurations were determined by using modified Mosher's method.

MeSH terms

  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / pharmacology
  • Crystallography, X-Ray
  • Furans / chemistry
  • Furans / pharmacology
  • Molecular Conformation
  • Molecular Structure
  • Pasteurella / drug effects
  • Streptomyces

Substances

  • Anti-Bacterial Agents
  • Furans
  • dihydrotetrodecamycin
  • tetrodecamycin