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Functional Characterization of a Novel Dactylosporangium Esterase and Its Utilization in the Asymmetric Synthesis of (R)-Methyl Mandelate

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Abstract

One novel esterase DAEst6 was identified from the genome of Dactylosporangium aurantiacum subsp. Hamdenensis NRRL 18085. DAEst6 was further characterized to be an esterase which exhibited high resistance to high pH values. Esterase DAEst6 could resolve racemic methyl mandelate and generate (R)-methyl mandelate, one key drug intermediate, with an enantiomeric excess and a conversion of 99 and 49 %, respectively, after process optimization. The optimal working condition for the preparation of (R)-methyl mandelate through DAEst6 was found to be 10-mM racemic methyl mandelate, no organic co-solvents, pH 7.5, and 40 °C, for 5 h. Our work was the first report about the functional characterization of one novel Dactylosporangium esterase and the utilization of one Dactylosporangium esterase in kinetic resolution. Dactylosporangium esterases represented by DAEst6 possess great potential in the generation of valuable chiral drug intermediates and chemicals.

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Acknowledgments

We are grateful for the financial supports from National Natural Science Foundation of China (No. 21302199), Strategic Priority Research Program of the Chinese Academy of Sciences (XDA11030404), 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). We also would like to thank the constant help from Professor Changsheng Zhang and Professor Jianhua Ju.

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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

    Dun Deng, Yun Zhang, Aijun Sun & Yunfeng Hu

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

    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

    Dun Deng, Yun Zhang, Aijun Sun & 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. Dun Deng
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  2. Yun Zhang
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Correspondence to Yunfeng Hu.

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Deng, D., Zhang, Y., Sun, A. et al. Functional Characterization of a Novel Dactylosporangium Esterase and Its Utilization in the Asymmetric Synthesis of (R)-Methyl Mandelate. Appl Biochem Biotechnol 180, 228–247 (2016). https://doi.org/10.1007/s12010-016-2095-7

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  • DOI: https://doi.org/10.1007/s12010-016-2095-7

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