Novel beta-lactam antibiotics synthesized by amination of catechols using fungal laccase

Chem Pharm Bull (Tokyo). 2008 Jul;56(7):902-7. doi: 10.1248/cpb.56.902.

Abstract

Novel cephalosporins, penicillins, and carbacephems were synthesized by amination of catechols with amino-beta-lactams like cefadroxil, amoxicillin, ampicillin and the structurally related carbacephem loracarbef using laccase from Trametes sp. All isolated monoaminated products inhibited the growth of several Gram positive bacterial strains in the agar diffusion assay, among them methicillin-resistant Staphylococcus aureus strains and vancomycin-resistant Enterococci. Observed differences in the cytotoxicity and in vivo activity in a "Staphylococcus-infected, immune suppressed mouse" model are discussed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amination
  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / pharmacology
  • Catalysis
  • Catechols / chemistry*
  • Fungi / enzymology
  • Laccase / metabolism*
  • Structure-Activity Relationship
  • beta-Lactams / chemical synthesis*
  • beta-Lactams / pharmacology

Substances

  • Anti-Bacterial Agents
  • Catechols
  • beta-Lactams
  • Laccase