Studies on the biosynthesis of bialaphos (SF-1293) 12. C-P bond formation mechanism of bialaphos: discovery of a P-methylation enzyme

J Antibiot (Tokyo). 1992 May;45(5):781-7. doi: 10.7164/antibiotics.45.781.


An enzymatic activity catalyzing P-methylation of N-acetyldemethylphosphinothricin, a biosynthetic intermediate of the herbicide bialaphos, was detected in a cell extract of Streptomyces hygroscopicus SF-1293, a bialaphos producing organism. The gene coding for this P-methylation enzyme in the bialaphos biosynthetic gene cluster was also expressed in Streptomyces lividans. The methyl donor of the reaction was determined to be methylcobalamin. The P-methylation enzyme utilized both N-acetyldemethylbialaphos and N-acetyldemethylphosphinothricin as substrates.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Herbicides / metabolism*
  • Herbicides / pharmacology
  • Methylation / drug effects
  • Multigene Family
  • Organophosphorus Compounds / metabolism*
  • Organophosphorus Compounds / pharmacology
  • Streptomyces / genetics
  • Streptomyces / metabolism*
  • Substrate Specificity


  • Herbicides
  • Organophosphorus Compounds
  • bialaphos