Asymmetric synthesis of BB-3497--a potent peptide deformylase inhibitor

Bioorg Med Chem Lett. 2001 Oct 8;11(19):2585-8. doi: 10.1016/s0960-894x(01)00509-1.

Abstract

By screening a library of metalloenzyme inhibitors, the N-formyl-hydroxylamine derivative BB-3497 was identified as a potent inhibitor of Escherichia coli peptide deformylase with antibacterial activity both in vitro and in vivo. The homochiral synthesis of BB-3497, involving a novel asymmetric Michael addition reaction is described.

MeSH terms

  • Amidohydrolases*
  • Aminopeptidases / antagonists & inhibitors*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Crystallography, X-Ray
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology
  • Hydroxamic Acids / chemical synthesis*
  • Hydroxamic Acids / chemistry
  • Hydroxamic Acids / pharmacology
  • Molecular Conformation
  • Structure-Activity Relationship

Substances

  • Anti-Bacterial Agents
  • BB3497
  • Enzyme Inhibitors
  • Hydroxamic Acids
  • Aminopeptidases
  • Amidohydrolases
  • peptide deformylase
  • actinonin