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Catalysis Letters

, Volume 149, Issue 2, pp 629–637 | Cite as

Exploring the Biocatalytic Scope of a Novel Enantioselective Halohydrin Dehalogenase from an Alphaproteobacterium

  • Feng XueEmail author
  • Xiangju Ya
  • Yuansong Xiu
  • Qi Tong
  • Yuqi Wang
  • Xinhai Zhu
  • He HuangEmail author
Article
  • 20 Downloads

Abstract

A gene encoding halohydrin dehalogenase from an alphaproteobacterium (AbHHDH) was identified, cloned and over-expressed in Escherichia coli. AbHHDH was able to catalyze the stereoselective dehalogenation of prochiral and racemic halohydrins. It showed the highest enantioselectivity in the dehalogenation of 20 mM (R,S)-2-bromo-1-phenylethanol, which yielded (S)-2-bromo-1-phenylethanol with 99% ee and 34.5% yield. Moreover, AbHHDH catalyzed the azidolysis of epoxides with low to moderate (S)-enantioselectivity. The highest enantioselectivity (E = 18.6) was observed when (R,S)-benzyl glycidyl ether was used as the substrate. A sequential kinetic resolution catalyzed by HHDH was employed for the synthesis of chiral 1-chloro-3-phenoxy-2-propanol. We prepared enantiopure (S)-isomer with a high enantiopurity of ee > 99% and a yield of 30.7% (E-value: 21.3) by kinetic resolution of 20 mM substrate. The (S)-isomer with 99% ee readily obtained from 40 to 150 mM (R,S)-1-chloro-3-phenoxy-2-propanol. Taken together, the results of this study demonstrate the applicability of this HHDH for the production of optically active compounds.

Keywords

Halohydrin dehalogenase Epoxides Halohydrins Enantioselectivity Biocatalysis 

Notes

Acknowledgements

This project was sponsored by the National Natural Science Foundation of China (No. 21606192), the Natural Science Foundation of the Jiangsu Higher Education Institutions of China (No. 16KJB180029) and the China Postdoctoral Science Foundation (No. 2016M601795).

Compliance with Ethical Standards

Conflict of interest

The authors declared that they have no conflicts of interest to this work.

Supplementary material

10562_2019_2659_MOESM1_ESM.docx (426 kb)
Supplementary material 1 (DOCX 426 KB)

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  1. 1.School of Marine and BioengineeringYancheng Institute of TechnologyYanchengPeople’s Republic of China
  2. 2.College of Pharmaceutical ScienceNanjing Tech UniversityNanjingPeople’s Republic of China
  3. 3.School of Environmental and Chemical EngineeringJiangsu University of Science and TechnologyZhenjiangPeople’s Republic of China

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