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Enantioconvergent bioconversion of p-chlorostyrene oxide to (R)-p-chlorophenyl-1,2-ethandiol by the bacterial epoxide hydrolase of Caulobacter crescentus

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Abstract

The enantioselective hydrolysis of eight racemic styrene oxide derivatives has been investigated by using the recombinant cell containing epoxide hydrolase (EH) of Caulobacter crescentus. Some styrene oxide derivatives were hydrolyzed via enantioconvergent manner so that enantiopure diol products could be prepared with a 100% theoretical yield. The recombinant cell containing C. crescentus EH exhibited an ability to hydrolyze racemic p-chlorostyrene oxide the most enantioconvergently, thus affording the formation of the corresponding (R)-diol with enantiomeric excess (ee) as high as 95% and a 72% yield in preparative-scale (16.8 g/l) bioconversion.

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Acknowledgments

This work was supported by the Marine and Extreme Genome Research Center Program, Ministry of Marine Affairs and Fisheries, Republic of Korea.

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Authors and Affiliations

  1. Department of Chemical and Biological Engineering, Seoul National University, Seoul, 151-742, Korea

    Seungha Hwang & Cha Yong Choi

  2. Department of Chemical Engineering and Green Energy Center, Kyung Hee University, Gyeonggi-do, 446-701, Korea

    Eun Yeol Lee

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  1. Seungha Hwang
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  2. Cha Yong Choi
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  3. Eun Yeol Lee
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Correspondence to Eun Yeol Lee.

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Hwang, S., Choi, C.Y. & Lee, E.Y. Enantioconvergent bioconversion of p-chlorostyrene oxide to (R)-p-chlorophenyl-1,2-ethandiol by the bacterial epoxide hydrolase of Caulobacter crescentus . Biotechnol Lett 30, 1219–1225 (2008). https://doi.org/10.1007/s10529-008-9668-7

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  • DOI: https://doi.org/10.1007/s10529-008-9668-7

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