Biosynthesis of (R)-phenyl-1,2-ethanediol from racemic styrene oxide by using bacterial and marine fish epoxide hydrolases

Biotechnol Lett. 2008 Jan;30(1):127-33. doi: 10.1007/s10529-007-9495-2. Epub 2007 Jul 31.

Abstract

Enantio-convergent hydrolysis of racemic styrene oxides was achieved to prepare enantiopure (R)-phenyl-1,2-ethanediol by using two recombinant epoxide hydrolases (EHs) of a bacterium, Caulobacter crescentus, and a marine fish, Mugil cephalus. The recombinant C. crescentus EH primarily attacked the benzylic carbon of (S)-styrene oxide, while the M. cephalus EH preferentially attacked the terminal carbon of (R)-styrene oxide, thus leading to the formation of (R)-phenyl-1,2-ethanediol as the main product. (R)-Phenyl-1,2-ethanediol was obtained with 90% enantiomeric excess and yield as high as 94% from 50 mM racemic styrene oxides in a one-pot process.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Caulobacter crescentus / enzymology*
  • Caulobacter crescentus / genetics*
  • Epoxy Compounds / chemistry*
  • Ethylene Glycols / chemical synthesis*
  • Fishes / metabolism*
  • Hydrolases / chemistry*
  • Marine Biology
  • Recombinant Proteins / chemistry

Substances

  • Epoxy Compounds
  • Ethylene Glycols
  • Recombinant Proteins
  • styrene glycol
  • styrene oxide
  • Hydrolases