Enzymatic synthesis of monocyclic beta-lactams

Bioorg Med Chem Lett. 2002 Feb 25;12(4):597-9. doi: 10.1016/s0960-894x(01)00806-x.

Abstract

An Mg2+ and ATP dependent beta-lactam synthetase (BLS) catalyses formation of a beta-lactam ring during the biosynthesis of clavulanic acid, an important beta-lactamase inhibitor. An epimeric mixture of a 2-methylated derivative of the natural BLS substrate N2-(2-carboxyethyl)-L-arginine was synthesised and found to be a substrate for the enzyme. The epimeric products were characterised by 1H NMR and mass spectrometric analyses. The results suggest that a modified version of BLS might be used to catalyse the preparation of intermediates useful for the synthesis of beta-lactam antibiotics.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amidohydrolases / genetics
  • Amidohydrolases / metabolism*
  • Arginine / analogs & derivatives*
  • Arginine / analysis
  • Arginine / metabolism
  • Escherichia coli / metabolism
  • Mass Spectrometry
  • Monobactams / biosynthesis*
  • Nuclear Magnetic Resonance, Biomolecular
  • Stereoisomerism
  • Transformation, Genetic

Substances

  • Monobactams
  • octopine
  • Arginine
  • Amidohydrolases
  • beta-lactam synthetase