An efficient and practical method for solid-phase synthesis of tripeptide-bearing glycopeptide antibiotics: combinatorial parallel synthesis of carboxamide derivatives of chloroorienticin B

Bioorg Med Chem Lett. 2002 Nov 4;12(21):3033-6. doi: 10.1016/s0960-894x(02)00665-0.

Abstract

An efficient and practical method was established for solid-phase parallel synthesis of the peptide-bearing carboxamide derivatives of chloroorienticin B, and over 80 compounds were synthesized simultaneously. Among the derivatives prepared, compounds having both tryptophan and tyrosine residues (1-3) were found to possess potent antibacterial activity against VRE.

MeSH terms

  • Amides / chemical synthesis*
  • Amides / chemistry
  • Amides / pharmacology*
  • Amino Acids / chemistry
  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Combinatorial Chemistry Techniques
  • Enterococcus / drug effects
  • Methicillin Resistance*
  • Microbial Sensitivity Tests
  • Oligopeptides / chemical synthesis*
  • Oligopeptides / chemistry
  • Oligopeptides / pharmacology*
  • Staphylococcus aureus / drug effects
  • Vancomycin / analogs & derivatives
  • Vancomycin / chemical synthesis*
  • Vancomycin / chemistry
  • Vancomycin / pharmacology*
  • Vancomycin Resistance*

Substances

  • Amides
  • Amino Acids
  • Anti-Bacterial Agents
  • Oligopeptides
  • chloroorienticin B
  • Vancomycin