New semisynthetic glycopeptides MDL 63,246 and MDL 63,042, and other amide derivatives of antibiotic A-40,926 active against highly glycopeptide-resistant VanA enterococci

J Antibiot (Tokyo). 1995 Aug;48(8):869-83. doi: 10.7164/antibiotics.48.869.

Abstract

A series of amide derivatives of natural glycopeptide A-40,926 (A), its 6B-methyl ester (MA) and 6B-decarboxy-6B-hydroxymethyl derivative (RA) were prepared with the aim of obtaining activity against glycopeptide-resistant enterococci. These compounds are structurally related to a class of amides of 34-de(acetylglucosaminyl)-34-deoxy teicoplanin which showed interesting activity against strains of Enterococcus faecalis and E. faecium highly resistant to both vancomycin and teicoplanin. Among them, RA-amides MDL 63,246 and MDL 63,042 were the most active derivatives against several Gram-positive bacteria, including VanB and VanC enterococci, and were moderately active (MIC range 0.5 approximately 64 micrograms/ml) against strains of Enterococcus for which vancomycin and teicoplanin MICs were > or = 128 micrograms/ml. The chemical rationale and the synthesis of these new series of glycopeptide derivatives are described. Preliminary in vitro data are reported and structure-activity relationships are discussed.

Publication types

  • Comparative Study

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Chromatography, High Pressure Liquid
  • Drug Resistance, Microbial
  • Enterococcus / drug effects*
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Structure-Activity Relationship
  • Teicoplanin / analogs & derivatives
  • Teicoplanin / chemical synthesis
  • Teicoplanin / chemistry
  • Teicoplanin / pharmacology
  • Vancomycin / pharmacology

Substances

  • A 40926
  • Anti-Bacterial Agents
  • MDL 63042
  • Teicoplanin
  • Vancomycin
  • MDL 63246