有机化学 ›› 2005, Vol. 25 ›› Issue (10): 1198-1207. 上一篇    下一篇

综述与进展

Baeyer-Villiger单加氧酶在有机合成中的应用

姜标,罗军,黄浩,陈颖,李祖义*   

  1. (中国科学院上海有机化学研究所 上海 200032)
  • 收稿日期:2005-01-05 修回日期:2005-07-27 发布日期:2005-10-08
  • 通讯作者: 李祖义

Applications of Baeyer-Villiger Monooxygenase in Organic Synthesis

JIANG Biao,LUO Jun,HUANG Hao,CHEN Ying,LI Zu-Yi*   

  1. (Shanghai Institute of Organic chemistry, Chinese Academy of Sciences, Shanghai 200032)
  • Received:2005-01-05 Revised:2005-07-27 Published:2005-10-08
  • Contact: LI Zu-Yi

综述了Baeyer-Villiger单加氧酶在有机合成中的应用.较之传统的化学反应, 氧化酶催化剂反应有较好的选择性、可控性和经济性. 环己酮加氧酶是一种还原型辅酶I (NADPH)依赖型氧化酶, 是最早被报道能够催化Baeyer-Villiger氧化的酶. 这些重要反应产生了合成化学家很感兴趣的扩环产物. 环己酮加氧酶也是有用的生物催化剂, 由于辅酶再生的问题已被工程菌克服了, 所以能像全细胞催化剂那样使用. 对酮包括杂环酮进行Baeyer-Villiger氧化和动态动力学拆分, 放大这种反应作为合成路线是很有前途的.

关键词: Baeyer-Villiger氧化, 单加氧酶, 辅酶再生

The applications of Baeyer-Villiger monooxygenase in organic synthesis was discribed. Oxidizing enzymes were highly sought after because of the selectivity, controllability and economy of their reactions, in comparison with conventional chemical reactions. Cyclohexanone monooxygenase, an NADPH- dependent oxygenase, was the first enzyme reported to be capable of catalyzing Baeyer-Villiger oxidations. These important reactions could yield ring-expanded products of significant interest to the synthetic chemist. Cyclohexanone monooxygenase is also an example of a useful biocatalyst. Here, cofactor recycle constraints were overcome by using engineered strains as whole cell biocatalysts. For Baeyer-Villiger oxidations of ketones, including heterocyclic ketones and dynamic kinetic resolution, scale-up of such reactions will hold much promise as a synthetic route.

Key words: cofactor recycle, monooxygenase, Baeyer-Villiger oxidation