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Functional Characterization of a Robust Marine Microbial Esterase and Its Utilization in the Stereo-Selective Preparation of Ethyl (S)-3-Hydroxybutyrate

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Abstract

One novel microbial esterase PHE21 was cloned from the genome of Pseudomonas oryzihabitans HUP022 identified from the deep sea of the Western Pacific. PHE21 was heterologously expressed and functionally characterized to be a robust esterase which behaved high resistance to various metal ions, organic solvents, surfactants, and NaCl. Despite the fact that the two enantiomers of ethyl 3-hydroxybutyrate were hard to be enzymatically resolved before, we successfully resolved racemic ethyl 3-hydroxybutyrate through direct hydrolysis reactions and generated chiral ethyl (S)-3-hydroxybutyrate using esterase PHE21. After process optimization, the enantiomeric excess, the conversion rate, and the yield of desired product ethyl (S)-3-hydroxybutyrate could reach 99, 65, and 87 %, respectively. PHE21 is a novel marine microbial esterase with great potential in asymmetric synthesis as well as in other industries.

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Acknowledgments

We would like to thank 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 project “Engineering High-Performance Microorganisms for Advanced Bio-Based Manufacturing” from the Chinese Academy of Sciences (KGZD-EW-606). We thank the research vessel KEXUE of the Chinese Academy of Sciences for collecting samples and WPOS sample center for providing samples. Constant help from Professor Jianhua Ju and Professor Changsheng Zhang is also greatly appreciated.

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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

    Yilong Wang, Yun Zhang & Yunfeng Hu

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

    Yilong Wang

  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

    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. Yilong Wang
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  2. Yun Zhang
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Correspondence to Yunfeng Hu.

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Wang, Y., Zhang, Y. & Hu, Y. Functional Characterization of a Robust Marine Microbial Esterase and Its Utilization in the Stereo-Selective Preparation of Ethyl (S)-3-Hydroxybutyrate. Appl Biochem Biotechnol 180, 1196–1212 (2016). https://doi.org/10.1007/s12010-016-2161-1

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  • DOI: https://doi.org/10.1007/s12010-016-2161-1

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