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Progress in Chemistry 2010, Vol. 22 Issue (07): 1397-1402 Previous Articles   Next Articles

• Invited Article •

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: Online: Published:
  • Contact: Wang Meixiang E-mail:mxwang@iccas.ac.cn
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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

Key words: Rhodococcus erythropolis AJ270, biocatalysis and biotransformation, enantioselectivity, nitriles, amides

CLC Number: 

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