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化学进展 2017, Vol. 29 Issue (5): 491-501 DOI: 10.7536/PC170222 前一篇   后一篇

• 综述 •

手性芳基醇的生物催化不对称合成

白东亚1, 何军邀2*, 欧阳斌1, 黄金1, 王普1*   

  1. 1. 浙江工业大学药学院 杭州 310014;
    2. 浙江医药高等专科学校制药工程学院 宁波 315100
  • 收稿日期:2017-02-24 修回日期:2017-04-24 出版日期:2017-05-15 发布日期:2017-05-10
  • 通讯作者: 何军邀, 王普 E-mail:hejunyao1974@126.com;wangpu@zjut.edu.cn
  • 基金资助:
    国家自然科学基金项目（No.21676250），浙江省自然科学基金项目（No.LY16B060010），浙江省公益技术研究项目（No.2015C33137）和宁波市科技创新团队项目（No.2015C110027）资助
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Biocatalytic Asymmetric Synthesis of Chiral Aryl Alcohols

Dongya Bai1, Junyao He2*, Bin Ouyang1, Jin Huang1, Pu Wang1*   

  1. 1. College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, China;
    2. Department of Pharmaceutical Engineering, Zhejiang Pharmaceutical College, Ningbo 315100, China
  • Received:2017-02-24 Revised:2017-04-24 Online:2017-05-15 Published:2017-05-10
  • Supported by:
    The work was supported by the National Natural Science Foundation of China (No.21676250),the Zhejiang Provincial Natural Science Foundation of China (No.LY16B060010),the Program of Science and Technology of Zhejiang Province,China (No.2015C33137),and the Program of Ningbo Science and Technology Innovation Team (No.2015C110027).
光学活性芳基醇化合物是一类重要的手性砌块，可用于合成多种手性药物，其制备技术研究是近年来的研究热点。与传统的化学制备方法相比，生物催化方法由于具有选择性高、反应条件温和以及环境危害少等优点更具吸引力。通过生物催化不对称还原芳基酮是合成对映体纯芳基醇最有效的方法之一。本文综述了生物催化不对称还原制备手性芳基醇的研究进展，重点介绍了不同形式的生物催化剂应用于生物不对称还原的研究现状，包括微生物细胞、酶、重组工程菌以及固定化细胞等，概述了有机溶剂、表面活性剂和离子液体等底物助溶剂对生物不对称催化的影响，并对生物催化制备对映体纯芳基醇的研究前景进行了展望。
关键词： 芳基醇, 手性药物, 生物催化, 不对称合成, 助溶剂
Optically active aryl alcohols are a kind of important chiral building blocks for the synthesis of chiral drugs. In recent years, the preparations of enantiopure aryl alcohols have become one of the focus points in organic chemistry. Compared with conventional chemical processes, biocatalysis is more attractive due to its high enantioselectivity, mild and safe reaction conditions and less environmental hazards. Asymmetric bioreduction of aryl ketones is the most effective method for the synthesis of enantiopure aryl alcohols. This paper mainly reviews the recent progress in the preparation of chiral aryl alcohols by asymmetric bioreduction catalyzed by microbial whole-cells, enzymes, genetically engineered bacteria or yeasts, as well as immobilized cells. The effects of substrate co-solvents such as organic solvents, surfactants and ionic liquids on asymmetric bioreduction are further summarized. The prospect of the preparation of enantiopure aryl alcohols by asymmetric bioreduction is also discussed.
Contents
1 Introduction
2 Bioreduction of aryl ketones by microbial whole cells
2.1 Biocatalysis by eukaryotic microbes
2.2 Biocatalysis by prokaryotic microbes
3 Bioreduction of aryl ketones by plant cells
4 Bioreduction of aryl ketones by purified enzymes
5 Bioreduction of aryl ketones by recombinant whole cells
6 Bioreduction of aryl ketones by immobilized cells
7 Effects of substrate co-solvents on the bioreduction
7.1 Organic solvents as co-solvent
7.2 Surfactants as co-solvent
7.3 Ionic liquids as co-solvent
8 Conclusion
Key words: aryl alcohol, chiral drugs, biocatalysis, asymmetric synthesis, co-solvent

中图分类号: 

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