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.
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U2 - 10.1002/bit.20860
DO - 10.1002/bit.20860
M3 - Article
C2 - 16498626
AN - SCOPUS:33745211891
SN - 0006-3592
VL - 94
SP - 522
EP - 529
JO - Biotechnology and bioengineering
JF - Biotechnology and bioengineering
IS - 3
ER -