Bio-resolution of glycidyl (o, m, p)-methylphenyl ethers by Bacillus megaterium

Biotechnol Lett. 2010 Apr;32(4):513-6. doi: 10.1007/s10529-009-0181-4. Epub 2009 Dec 16.

Abstract

A newly isolated Bacillus megaterium with epoxide hydrolase activity resolved racemic glycidyl (o, m, p)-methylphenyl ethers to give enantiopure epoxides in 84-99% enantiomeric excess and with 21-73 enantiomeric ratios. The (S)-enantiomer was obtained from rac-glycidyl (o or m)-methylphenyl ether while the (R)-epoxides was obtained from glycidyl p-methylphenyl ether. The observations are explained at the level by enzyme-substrate docking studies.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anisoles / chemistry
  • Anisoles / isolation & purification*
  • Anisoles / metabolism
  • Bacillus megaterium / chemistry
  • Bacillus megaterium / metabolism*
  • Epoxy Compounds / chemistry
  • Epoxy Compounds / isolation & purification*
  • Epoxy Compounds / metabolism
  • Hydrolysis
  • Kinetics
  • Stereoisomerism

Substances

  • Anisoles
  • Epoxy Compounds
  • glycidyl ethers