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Biotechnology Letters

, Volume 39, Issue 12, pp 1917–1923 | Cite as

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

  • Rui Wang
  • Die Hu
  • Xuncheng Zong
  • Jinping li
  • Lei Ding
  • Minchen Wu
  • Jianfang li
Original Research Paper

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.

Keywords

Bi-enzymatic catalysis Enantioconvergent hydrolysis Epoxide hydrolase High substrate Concentration (R)-Phenyl-1,2-ethanediol Styrene oxide 

Notes

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.

Supplementary material

10529_2017_2433_MOESM1_ESM.docx (32 kb)
Supplementary material 1 (DOCX 31 kb)

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Copyright information

© Springer Science+Business Media B.V. 2017

Authors and Affiliations

  • Rui Wang
    • 1
  • Die Hu
    • 1
  • Xuncheng Zong
    • 1
  • Jinping li
    • 2
  • Lei Ding
    • 2
  • Minchen Wu
    • 2
  • Jianfang li
    • 3
  1. 1.Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of BiotechnologyJiangnan UniversityWuxiPeople’s Republic of China
  2. 2.Wuxi Medical SchoolJiangnan UniversityWuxiPeople’s Republic of China
  3. 3.School of Food Science and TechnologyJiangnan UniversityWuxiPeople’s Republic of China

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