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

Li Cao, Jintae Lee, Wilfred Chen, Thomas K. Wood

Research output: Contribution to journalArticle

64 Citations (Scopus)

Abstract

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.

Original languageEnglish (US)
Pages (from-to)522-529
Number of pages8
JournalBiotechnology and bioengineering
Volume94
Issue number3
DOIs
StatePublished - Jun 20 2006

Fingerprint

styrene oxide
Epoxide Hydrolases
Hydrolases
Agrobacterium tumefaciens
Solanum tuberosum
Styrene
Oxides
Carboxylesterase
Enantiomers
Enantioselectivity
Substrates
Drug products
Hydrolysis
Bacteria
Enzymes
styrene glycol
Pharmaceutical Preparations

All Science Journal Classification (ASJC) codes

  • Biotechnology
  • Bioengineering
  • Applied Microbiology and Biotechnology

Cite this

@article{d7aacdbd8e10464aa60ec1d5c4ede43f,
title = "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",
abstract = "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.",
author = "Li Cao and Jintae Lee and Wilfred Chen and Wood, {Thomas K.}",
year = "2006",
month = "6",
day = "20",
doi = "10.1002/bit.20860",
language = "English (US)",
volume = "94",
pages = "522--529",
journal = "Biotechnology and Bioengineering",
issn = "0006-3592",
publisher = "Wiley-VCH Verlag",
number = "3",

}

TY - JOUR

T1 - 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

AU - Cao, Li

AU - Lee, Jintae

AU - Chen, Wilfred

AU - Wood, Thomas K.

PY - 2006/6/20

Y1 - 2006/6/20

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=33745211891&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33745211891&partnerID=8YFLogxK

U2 - 10.1002/bit.20860

DO - 10.1002/bit.20860

M3 - Article

C2 - 16498626

AN - SCOPUS:33745211891

VL - 94

SP - 522

EP - 529

JO - Biotechnology and Bioengineering

JF - Biotechnology and Bioengineering

SN - 0006-3592

IS - 3

ER -