Crystal structure of BRL 42715, C6-(N1-methyl-1,2,3-triazolylmethylene)penem, in complex with Enterobacter cloacae 908R beta-lactamase: evidence for a stereoselective mechanism from docking studies

J Am Chem Soc. 2005 Mar 16;127(10):3262-3. doi: 10.1021/ja0426241.

Abstract

BRL 42715, C6-(N1-methyl-1,2,3-triazolylmethylene)penem, is an active-site-directed inactivator of bacterial beta-lactamases. The crystal structure of Enterobacter cloacae 908R class C beta-lactamase in complex with BRL 42715, docking, and energy minimization studies explain stereoselectivity of the binding of C6-(heterocyclic methylene)penems against class C beta-lactamase.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography, X-Ray
  • Enterobacter cloacae / enzymology*
  • Lactams / chemistry*
  • Lactams / metabolism
  • Models, Molecular
  • Stereoisomerism
  • Thermodynamics
  • beta-Lactamases / chemistry*
  • beta-Lactamases / metabolism

Substances

  • Lactams
  • C6-(N1-methyl-1,2,3-trazolylmethylene)penem
  • beta-Lactamases