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Chinese Journal of Organic Chemistry >

2018 , Vol. 38 >Issue 5: 1185 - 1192

DOI: https://doi.org/10.6023/cjoc201710019

Articles

Functional Characterization of a New Antarctic Microbial Esterase EST112-2 and Its Use in the Preparation of Chiral Tertiary Alcohol (S)-Linalool

  • Deng Dun ,
  • Zhang Yun ,
  • Sun Aijun ,
  • Sai Ke ,
  • Hu Yunfeng
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  • a CAS Key Laboratory of Tropical Marine Bio-resources and Ecology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301;
    b Department of Neurosurgery/Neuro-oncology, Sun Yat-sen University Cancer Center, Guangzhou 510060;
    c Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301;
    d Institute of Animal Science, Guangdong Academy of Agricultural Science, Guangzhou 510640;
    e Collaborative Innovation Center for Cancer Medicine, Guangzhou 510060;
    f State Key Laboratory of Oncology in South China, Guangzhou 510060

Received date: 2017-12-17

  Revised date: 2017-12-26

  Online published: 2018-01-18

Supported by

Project supported by the Priority Research Program of the Chinese Academy of Sciences (No. XDA11030404), the Scientific and Technological Project of Ocean and Fishery from Guangdong Province (No. A201701C12), the Guangzhou Science and Technology Plan Projects (No. 201510010012) and the National Natural Science Foundation of China (No. 21302199).

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Abstract

Chiral tertiary alcohols (TAs) are key building blocks for the synthesis of many crucial flavor compounds and pharmaceuticals. The two enantiomers of tertiary alcohol, linalool, differ in odor. So, sustainable strategies for the manufacture of optically pure TAs represented by linalool, are highly desirable. But the enzymatic synthesis of chiral tertiary alcohols through kinetic resolution was not easily achieved, possibly because of the steric hindrance from the chemical structures of tertiary alcohols. Herein, we identified and functionally characterized a new microbial esterase EST112-2 from the antarctic sediments and utilized esterase EST112-2 as a green biocatalyst in the synthesis of chiral tertiary alcohol (S)-linalool through asymmetric hydrolysis of racemic linalyl acetate. Parameters such as pH, temperature, co-solvents, substrate concentrations, enzyme loading and reaction time were optimized for the kinetic resolutions. Desired chiral product (S)-linalool was finally obtained with an enantiomeric excess of over 66% and a yield of over 72% after process optimization. The enantiomeric excess of (S)-linalool prepared by esterase EST112-2 was much higher than that from previous reports.

Key words： biocatalysis; antarctic microbial esterase; kinetic resolution; chiral tertiary alcohol; (S)-linalool

Cite this article

Deng Dun , Zhang Yun , Sun Aijun , Sai Ke , Hu Yunfeng . Functional Characterization of a New Antarctic Microbial Esterase EST112-2 and Its Use in the Preparation of Chiral Tertiary Alcohol (S)-Linalool[J]. Chinese Journal of Organic Chemistry, 2018 , 38(5) : 1185 -1192 . DOI: 10.6023/cjoc201710019

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