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Functional Characterization of a Novel Marine Microbial Esterase and its Utilization in the Enantioselective Preparation of (R)-Methyl 2-Chloropropionate

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Abstract

Chiral 2-chloropropanoic acids and their ester derivatives are crucial intermediates in the synthesis of many chemicals, especially herbicides. The enzymatic synthesis of chiral 2-chloropropanoic acids and their ester derivatives by esterases was not easily achieved, because the structural difference between the two enantiomers was too small to be recognized by esterases. Herein, we report the expression and functional characterization of one novel low temperature-resistant esterase EST12–7 identified from the genome of Pseudonocardia antitumoralis SCSIO 01299 isolated from the sediments of the South China Sea. Biocatalyst EST12–7 could hydrolyze racemic methyl 2-chloropropinate and generate optically pure (R)-methyl 2-chloropropinate with high enantiomeric excess (>99 %) and conversion (>49 %) after process optimization. Notably, the addition of different surfactants and using surfactants of different concentrations in the kinetic resolution catalyzed by EST12–7 could greatly affect the enantiomeric excess and conversion rate of product (R)-methyl 2-chloropropinate.

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Acknowledgments

We would like to thank the financial supports from the Strategic Priority Research Program of the Chinese Academy of Sciences (XDA11030404), National Natural Science Foundation of China (No.21302199), Guangzhou Science and Technology Plan Projects (201510010012) and Key Project “Engineering High-Performance Microorganisms for Advanced Bio-Based Manufacturing” from the Chinese Academy of Sciences (KGZD-EW-606).

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Authors and Affiliations

  1. Key Laboratory of Tropical Marine Bio-resources and Ecology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, 510301, People’s Republic of China

    Yingying Cao, Dun Deng, Aijun Sun, Yun Zhang & Yunfeng Hu

  2. University of Chinese Academy of Sciences, Beijing, 100049, People’s Republic of China

    Yingying Cao & Dun Deng

  3. Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, 510301, People’s Republic of China

    Yingying Cao, Dun Deng, Aijun Sun, Yun Zhang & Yunfeng Hu

  4. South China Sea Bio-Resource Exploitation and Utilization Collaborative Innovation Center, Guangzhou, People’s Republic of China

    Yunfeng Hu

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  1. Yingying Cao
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  2. Dun Deng
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Correspondence to Yunfeng Hu.

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Cao, Y., Deng, D., Sun, A. et al. Functional Characterization of a Novel Marine Microbial Esterase and its Utilization in the Enantioselective Preparation of (R)-Methyl 2-Chloropropionate. Appl Biochem Biotechnol 180, 210–227 (2016). https://doi.org/10.1007/s12010-016-2094-8

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  • DOI: https://doi.org/10.1007/s12010-016-2094-8

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