A novel enantioselective epoxide hydrolase for (R)-phenyl glycidyl ether to generate (R)-3-phenoxy-1,2-propanediol

Appl Microbiol Biotechnol. 2007 Oct;76(6):1281-7. doi: 10.1007/s00253-007-1098-2. Epub 2007 Aug 21.

Abstract

Bacillus sp. Z018, a novel strain producing epoxide hydrolase, was isolated from soil. The epoxide hydrolase catalyzed the stereospecific hydrolysis of (R)-phenyl glycidyl ether to generate (R)-3-phenoxy-1,2-propanediol. Epoxide hydrolase from Bacillus sp. Z018 was inducible, and (R)-phenyl glycidyl ether was able to act as an inducer. The fermentation conditions for epoxide hydrolase were 35 degrees C, pH 7.5 with glucose and NH(4)Cl as the best carbon and nitrogen source, respectively. Under optimized conditions, the biotransformation yield of 45.8% and the enantiomeric excess of 96.3% were obtained for the product (R)-3-phenoxy-1,2-propanediol.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bacillus / enzymology*
  • Biomass
  • Biotransformation
  • Carbon / metabolism
  • Epoxide Hydrolases / chemistry
  • Epoxide Hydrolases / metabolism*
  • Epoxy Compounds / chemistry
  • Epoxy Compounds / metabolism*
  • Glycerol / analogs & derivatives*
  • Glycerol / chemistry
  • Glycerol / metabolism
  • Hydrogen-Ion Concentration
  • Molecular Conformation
  • Molecular Structure
  • Nitrogen / metabolism
  • Phenyl Ethers / chemistry
  • Phenyl Ethers / metabolism*
  • Propylene Glycols / chemistry
  • Propylene Glycols / metabolism*
  • Temperature

Substances

  • Epoxy Compounds
  • Phenyl Ethers
  • Propylene Glycols
  • glycidyl ethers
  • 3-phenoxy-1,2-propanediol
  • phenylglycidyl ether
  • Carbon
  • Epoxide Hydrolases
  • Nitrogen
  • Glycerol