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Enantioselective Resolution of (±)-1-Phenylethanol and (±)-1-Phenylethyl Acetate by a Novel Esterase from Bacillus sp. SCSIO 15121

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Abstract

A novel microbial esterase BSE01281 identified from the Indian Ocean was cloned, expressed, and functionally characterized. Esterase BSE01281 could enanoselectively resolve (±)-1-phenylethanol and (±)-1-phenylethyl acetate through two types of enzymatic reactions. After the optimization of enzymatic reactions, BSE01281 could efficiently generate (R)-1-phenylethyl acetate with high enantiomeric excess (>99 %) and high conversion (42 %) after 96 h trans-esterification reactions. Additionally, BSE01281 could also produce (R)-1-phenylethanol (e.e. > 99 %) and (S)-1-phenylethyl acetate (e.e. > 95 %) at a conversion of 49 % through direct hydrolysis of inexpensive racemic 1-phenylethyl acetate for 8 h. Optically pure (R)-1-phenylethanol generated from direct enzymatic hydrolysis of racemic 1-phenylethyl acetate by BSE01281 is not easily prepared by dehydrogenases, which generally follow the “Prelog’s rule” and give (S)-1-phenylethanol instead.

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Acknowledgments

We are grateful for the financial supports from National Natural Science Foundation of China (no. 21302199) and Strategic Priority Research Program of the Chinese Academy of Sciences (XDA11030404) and Project “Engineering High-Performance Microorganisms for Advanced Bio-Based Manufacturing” from the Chinese Academy of Sciences (KGZD-EW-606) and Guangzhou Science and Technology Plan Projects (201510010012). We also would like to thank the constant help from Professor Jianhua Ju and Professor Changsheng Zhang.

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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

    Jiayuan Liang, Yun Zhang, Aijun Sun, Dun Deng & Yunfeng Hu

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

    Jiayuan Liang, Yun Zhang, Aijun Sun, Dun Deng & Yunfeng Hu

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

    Yunfeng Hu

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  1. Jiayuan Liang
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Correspondence to Yunfeng Hu.

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Liang, J., Zhang, Y., Sun, A. et al. Enantioselective Resolution of (±)-1-Phenylethanol and (±)-1-Phenylethyl Acetate by a Novel Esterase from Bacillus sp. SCSIO 15121. Appl Biochem Biotechnol 178, 558–575 (2016). https://doi.org/10.1007/s12010-015-1894-6

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