Enzymatic resolution of chiral phosphinate esters

J Am Chem Soc. 2004 Jul 28;126(29):8888-9. doi: 10.1021/ja048457m.

Abstract

The bacterial phosphotriesterase has been shown to catalyze the stereoselective hydrolysis of phosphinate esters. The wild-type enzyme preferentially hydrolyzes the SP-enantiomers of methyl phenyl p-X-phenylphosphinate esters by 3 orders of magnitude. The mutant enzyme, I106T/F132A/H254G/H257W, exhibits the opposite stereoselectivity and hydrolyzes the RP-enantiomer up to 30 times faster than the corresponding SP-enantiomer. The enantiomerically pure phosphinate esters, prepared from the kinetic resolution of racemic mixtures, can serve as the entry point for the chemoenzymatic preparation of P-chiral phosphines and phosphine oxides.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Esters / chemical synthesis
  • Esters / chemistry*
  • Esters / isolation & purification
  • Phosphinic Acids / chemistry*
  • Phosphinic Acids / isolation & purification
  • Phosphoric Triester Hydrolases / chemistry*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Esters
  • Phosphinic Acids
  • Phosphoric Triester Hydrolases