Enantioconvergent production of (R)-1-phenyl-1,2-ethanediol from styrene oxide by combining the Solanum tuberosum and an evolved Agrobacterium radiobacter AD1 epoxide hydrolases
Article first published online: 23 FEB 2006
Copyright © 2006 Wiley Periodicals, Inc.
Biotechnology and Bioengineering
Volume 94, Issue 3, pages 522–529, 20 June 2006
How to Cite
Cao, L., Lee, J., Chen, W. and Wood, T. K. (2006), Enantioconvergent production of (R)-1-phenyl-1,2-ethanediol from styrene oxide by combining the Solanum tuberosum and an evolved Agrobacterium radiobacter AD1 epoxide hydrolases. Biotechnol. Bioeng., 94: 522–529. doi: 10.1002/bit.20860
- Issue published online: 9 MAY 2006
- Article first published online: 23 FEB 2006
- Manuscript Accepted: 27 DEC 2005
- Manuscript Received: 5 AUG 2005
- National Science Foundation. Grant Number: BES-0331416
- epoxide hydrolase;
- styrene oxide;
Soluble epoxide hydrolase (EH) from the potato Solanum tuberosum and an evolved EH of the bacterium Agrobacterium radiobacter AD1, EchA-I219F, were purified for the enantioconvergent hydrolysis of racemic styrene oxide into the single product (R)-1-phenyl-1,2-ethanediol, which is an important intermediate for pharmaceuticals. EchA-I219F has enhanced enantioselectivity (enantiomeric ratio of 91 based on products) for converting (R)-styrene oxide to (R)-1-phenyl-1,2-ethanediol (2.0 ± 0.2 µmol/min/mg), and the potato EH converts (S)-styrene oxide primarily to the same enantiomer, (R)-1-phenyl-1,2-ethanediol (22 ± 1 µmol/min/mg), with an enantiomeric ratio of 40 ± 17 (based on substrates). By mixing these two purified enzymes, inexpensive racemic styrene oxide (5 mM) was converted at 100% yield to 98% enantiomeric excess (R)-1-phenyl-1,2-ethanediol at 4.7 ± 0.7 µmol/min/mg. Hence, at least 99% of substrate is converted into a single stereospecific product at a rapid rate. © 2006 Wiley Periodicals, Inc.