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化学进展 2010, Vol. 22 Issue (07): 1397-1402 前一篇   后一篇

• 特约稿 •

含三元环腈的生物转化反应与应用*

王德先1    王梅祥1,2**   

  1. (1. 中国科学院化学研究所    北京  100190; 2. 清华大学化学系    北京  100084)
  • 收稿日期:2010-01-28 出版日期:2010-07-24 发布日期:2010-07-02
  • 通讯作者: 王梅祥 E-mail:mxwang@iccas.ac.cn
  • 基金资助:

    国家自然科学基金项目

Biotransformations of Three-Membered (Hetero) Cyclic Nitriles and Their Applications in Organic Synthesis

 Wang Dexian1    Wang  Meixiang1,2**   

  1. (1. Institute of Chemistry Chinese Academy of Science, Beijing 100190, China;2. Department of Chemistry, Tsinghua University, Beijing 100084, China)
  • Received:2010-01-28 Online:2010-07-24 Published:2010-07-02
  • Contact: Wang Meixiang E-mail:mxwang@iccas.ac.cn

腈的对映选择性生物转化反应是合成高光学活性羧酸及其酰胺衍生物的有力手段。 本文介绍了在红球菌AJ270催化下,一系列含三元环结构的腈,包括环丙腈、环氧丙腈和氮杂环丙腈的生物转化反应。提出了腈水合酶和酰胺水解酶酶活中心的假设,即腈水合酶可能位于比较疏散的立体空间环境中,而酰胺水解酶则处于相对深埋的位置且空间大小有限。另外本文还探讨了腈的生物催化反应在天然产物及生物活性分子合成中的应用。

Enantioselective biotransformations of nitriles using nitrile hydrolyzing microbial whole cell catalysts are a powerful method for the synthesis of highly enantiopure carboxylic acids and amide derivatives. In this article, progress of Rhodococcus erythropolis AJ270-catalyzed enantioselective biotransformations of nitriles including various cyclopropane-, oxirane-, and aziridine-containing carbonitriles is summarized. On the basis of the outcomes of the biotransformation study, it is proposed that a readily reachable reactive site be embedded within the spacious pocket of the nitrile hydratase while the amidase might comprise a relatively deep-buried and size-limited active site. Applications of enantioselective biotransformations of nitriles in the synthesis of natural and bioactive products are also discussed.

Contents 
1 Introduction 
2 Biocatalysis and biotransformations of three membered cyclic nitriles 
2.1 Biocatalysis and biotransformations of cyclopropane nitriles 
2.2 Biocatalysis and biotransformations of three-membered heterocyclic nitriles and amides 
2.3 Applications of biotransformations on the synthesis of natural products and bioactive molecules 
3 Conclusions and outlook

中图分类号: 

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