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Functional characterization of a novel microbial esterase identified from the Indian Ocean and its use in the stereoselective preparation of (R)-methyl mandelate

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Abstract

Genomic mining has identified a novel microbial alkaline esterase from the Indian Ocean. This esterase was overexpressed in E. coli BL21 (DE3) and further functionally characterized. Under optimal conditions (10 mmol/L substrate, pH 6.0, 2 h at 40 °C), this esterase can hydrolyze racemic methyl mandelate to (R)-methyl mandelate with very high optical purity (e.e. >99%) and yield (nearly 90%). Interestingly, the stereoselectivity of this esterase is opposite to that of two previously reported lipases that can generate (S)-methyl mandelate through the hydrolysis of racemic methyl mandelate. No organic solvents or other additives were required to optimize the optical purity and production of the final chiral product (R)-methyl mandelate, which can potentially simplify the production procedure of (R)-methyl mandelate catalyzed by esterase.

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Authors and Affiliations

  1. Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, 510301, China

    Jiayuan Liang  (梁甲元), Aijun Sun  (孙爱君), Yun Zhang  (张云), Dun Deng  (邓盾) & Yunfeng Hu  (胡云峰)

  2. Key Laboratory of Tropical Marine Bio-Resources and Ecology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, 510301, China

    Jiayuan Liang  (梁甲元), Aijun Sun  (孙爱君), Yun Zhang  (张云), Dun Deng  (邓盾) & Yunfeng Hu  (胡云峰)

  3. South China Sea Bio-Resource Exploitation and Utilization, Collaborative Innovation Center, Guangzhou, 510275, China

    Yunfeng Hu  (胡云峰)

  4. Department of Biotechnology, Jinan University, Guangzhou, 510632, China

    Yongfei Wang  (王永飞) & Sanmei Ma  (马三梅)

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  1. Jiayuan Liang  (梁甲元)
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  2. Aijun Sun  (孙爱君)
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  3. Yun Zhang  (张云)
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  4. Dun Deng  (邓盾)
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  5. Yongfei Wang  (王永飞)
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  6. Sanmei Ma  (马三梅)
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  7. Yunfeng Hu  (胡云峰)
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Corresponding author

Correspondence to Yunfeng Hu  (胡云峰).

Additional information

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

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Liang, J., Sun, A., Zhang, Y. et al. Functional characterization of a novel microbial esterase identified from the Indian Ocean and its use in the stereoselective preparation of (R)-methyl mandelate. Chin. J. Ocean. Limnol. 34, 1269–1277 (2016). https://doi.org/10.1007/s00343-016-5164-4

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  • DOI: https://doi.org/10.1007/s00343-016-5164-4

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