物理化学学报 >> 1996, Vol. 12 >> Issue (03): 218-223.doi: 10.3866/PKU.WHXB19960306

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Mycobacterium E3休止细胞催化烯烃立体选择性环氧化

夏什文,李树本,尉迟力,沈润南   

  1. 中国科学院兰州化学物理研究所羧基合成与选择氧化国家重点实验室，兰州 730000
  • 收稿日期:1995-06-12 修回日期:1995-09-18 发布日期:1996-03-15
  • 通讯作者: 夏什文

Stereoselective Epoxidation of Alkenes Catalyzed by Mycobacterium E3 Resting Cell

Xia Shi-Wen,Li Shu-Ben,Wei Chi-Li,Shen Run-Nan   

  1. State Key Laboratory of Oxo Synthesis and Selective Oxidation,Lanzhou Institute of Chemical Physics,Chinese Academy of Sciences,Lanzhou 730000
  • Received:1995-06-12 Revised:1995-09-18 Published:1996-03-15
  • Contact: Xia Shi-Wen

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摘要：

初步研究了Mycobacterium E3的生长和产酶特性，利用Mycobacterium E3休止细胞催化烷烃羟化和烯烃环氧化．研究结果表明，烷烃不能被羟化，烯烃环氧化具有底物选择性．对烯丙基型底物XCH2CH＝CH2（X＝H、Cl、Br、OH），取代基大小显著影响环氧化活性. Mycobacterium E3中烯烃单加氧酶和另一种结构未知的酶的存在导致烯烃环氧化过程中存在环氧化物的立体选择性形成和非立体选择性降解两种竞争反应，旋光技术和手性气相色谱揭示Mycobacterium E3催化相应烯烃主要形成（R）-1，2-环氧丙烷和（S）-1-氯-2，3-环氧丙烷。

关键词: Mycobacterium E3, 烯烃单加氧酶, 烯烃环氧化, 立体选择性

Abstract:

Growth Characteristics of Mycobacterium E3 on ethene in mineral salts medium and oxidation of alkanes and alkanes catalyzed by Mycobacterium E3 resting cell were studied. Mycobacterium E3 was unable to catalyze hydroxylation of alkanes, but able to catalyze epoxidation of alkenes specifically. Influence of substituents on epoxidizing activity was discussed for allyl substrates XCH2CH=CH2 (X=H, Cl, Br, OH). Alkene monooxygenase and an unknown enzyme in Mycobacterium E3 catalyzed stereoselective epoxidation of alkenes and not-stereoselective degradation of epoxides. Optical rotation and chiral capillary chromatography revealed that propene and 3-chloro-1-propene were epoxidized to (R)-1,2-epoxypropane and (S)-1-chloro-2,3- epoxypropane.

Key words: Mycobacterium E3, Alkene monooxygenase, Epoxidation of alkenes, Stereoselectivity