Syntheses of the P-methylase substrates of the bialaphos biosynthetic pathway

Org Lett. 2008 Dec 18;10(24):5521-4. doi: 10.1021/ol802269x.

Abstract

Genetic studies suggest that either N-acetyldemethyl phosphinothricin (1, N-AcDMPT) or N-acetyldemethyl phosphinothricin tripeptide (2, N-AcDMPTT) is the substrate for the P-methylation reaction in the biosynthesis of phosphinothricin tripeptide (PTT), which is widely used as an herbicide. To study the mechanism for this unique P-methylation reaction catalyzed by the BcpD protein and the functions of the unusual nonribosomal peptide synthetases involved in PTT biosynthesis, this work reports the chemical syntheses of 1 and 2.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aminobutyrates / chemical synthesis*
  • Aminobutyrates / chemistry
  • Herbicides / chemical synthesis*
  • Herbicides / chemistry
  • Methylation
  • Methyltransferases / chemistry
  • Methyltransferases / metabolism*
  • Oligopeptides / chemical synthesis*
  • Oligopeptides / chemistry
  • Organophosphonates / chemistry
  • Organophosphorus Compounds / chemical synthesis*
  • Organophosphorus Compounds / chemistry
  • Organophosphorus Compounds / metabolism*
  • Streptomyces / chemistry
  • Streptomyces / metabolism*

Substances

  • Aminobutyrates
  • Herbicides
  • Oligopeptides
  • Organophosphonates
  • Organophosphorus Compounds
  • N-acetyldemethylphosphinothricin
  • bialaphos
  • Methyltransferases
  • P-methyltransferase