Chemical modification of tylosin: synthesis of amino derivatives at C-20 position of tylosin and demycarosyltylosin

J Antibiot (Tokyo). 1983 Dec;36(12):1713-21. doi: 10.7164/antibiotics.36.1713.

Abstract

Reductive aminations of the aldehyde group at C-20 position of tylosin and demycarosyltylosin (desmycosin) were carried out using primary and secondary amines in the presence of sodium cyanoborohydride. Some of these derivatives brought about higher antimicrobial and ribosome-binding activities, and the structure-activity relationship is discussed.

MeSH terms

  • Animals
  • Anti-Bacterial Agents / chemical synthesis*
  • Indicators and Reagents
  • Leucomycins / chemical synthesis*
  • Leucomycins / toxicity
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Mice
  • Microbial Sensitivity Tests
  • Ribosomes / drug effects
  • Ribosomes / metabolism
  • Structure-Activity Relationship
  • Tylosin

Substances

  • Anti-Bacterial Agents
  • Indicators and Reagents
  • Leucomycins
  • 4'-dexydemycarosyltylosin
  • Tylosin