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Enantioconvergent hydrolysis of racemic styrene oxide at high concentration by a pair of novel epoxide hydrolases into (R)-phenyl-1,2-ethanediol

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Abstract

Objectives

To prepare (R)-phenyl-1,2-ethanediol ((R)-PED) with high enantiomeric excess (ee p) and yield from racemic styrene oxide (rac-SO) at high concentration by bi-enzymatic catalysis.

Results

The bi-enzymatic catalysis was designed for enantioconvergent hydrolysis of rac-SO by a pair of novel epoxide hydrolases (EHs), a Vigna radiata EH3 (VrEH3) and a variant (AuEH2A250I) of Aspergillus usamii EH2. The simultaneous addition mode of VrEH3 and AuEH2A250I, exhibiting the highest average turnover frequency (aTOF) of 0.12 g h−1 g−1, was selected, by which rac-SO (10 mM) was converted into (R)-PED with 92.6% ee p and 96.3% yield. Under the optimized reaction conditions: dry weight ratio 14:1 of VrEH3-expressing E. coli/vreh3 to AuEH2A250I-expressing E. coli/Aueh2 A250I and reaction at 20 °C, rac-SO (10 mM) was completely hydrolyzed in 2.3 h, affording (R)-PED with 98% ee p. At the weight ratio 0.8:1 of rac-SO to two mixed dry cells, (R)-PED with 97.4% ee p and 98.7% yield was produced from 200 mM (24 mg/ml) rac-SO in 10.5 h.

Conclusions

Enantioconvergent hydrolysis of rac-SO at high concentration catalyzed by both VrEH3 and AuEH2A250I is an effective method for preparing (R)-PED with high ee p and yield.

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Acknowledgements

This work was financially supported by the National Nature Science Foundation of China (21 676 117). The authors are greatful to Prof. Xianzhang Wu (School of Biotechnology, Jiangnan University) for providing technical assistance.

Supplementary information

Supplementary methods—the expression and activity assay of VrEH3 and AuEH2A250I.

Author information

Author notes

  1. Rui Wang and Die Hu, the two first authors, have contributed equally to this work.

Authors and Affiliations

  1. Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Wuxi, 214122, People’s Republic of China

    Rui Wang, Die Hu & Xuncheng Zong

  2. Wuxi Medical School, Jiangnan University, Wuxi, 214122, People’s Republic of China

    Jinping li, Lei Ding & Minchen Wu

  3. School of Food Science and Technology, Jiangnan University, Wuxi, 214122, People’s Republic of China

    Jianfang li

Authors
  1. Rui Wang
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  2. Die Hu
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  3. Xuncheng Zong
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  4. Jinping li
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  5. Lei Ding
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  6. Minchen Wu
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  7. Jianfang li
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Corresponding author

Correspondence to Minchen Wu.

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Wang, R., Hu, D., Zong, X. et al. Enantioconvergent hydrolysis of racemic styrene oxide at high concentration by a pair of novel epoxide hydrolases into (R)-phenyl-1,2-ethanediol. Biotechnol Lett 39, 1917–1923 (2017). https://doi.org/10.1007/s10529-017-2433-z

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  • DOI: https://doi.org/10.1007/s10529-017-2433-z

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