Asymmetric epoxidation of styrene derivatives by styrene monooxygenase from Pseudomonas sp LQ26: effects of α- and β-substituents

被引：24
|
作者：
Lin, Hui [1 ,2 ]
Liu, Yan [1 ]
Wu, Zhong-Liu [1 ]
机构：
[1] Chinese Acad Sci, Chengdu Inst Biol, Chengdu 610041, Sichuan, Peoples R China
[2] Chinese Acad Sci, Grad Sch, Beijing 100039, Peoples R China
来源：
TETRAHEDRON-ASYMMETRY | 2011年 / 22卷 / 02期
基金：
中国国家自然科学基金;
关键词：
CHIRAL OXIRANES; EPOXIDES; SCALE; BIOCHEMISTRY; GENETICS; OLEFINS;
D O I：
10.1016/j.tetasy.2010.12.022
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Recombinant Escherichia coli expressing a styrene monooxygenase, StyAB2, from Pseudomonas sp. LQ26 was applied to synthesize a range of chiral epoxides from conjugated styrene derivatives with excellent (>99%) enantioselectivity in most cases. The substrate preference was studied with a special focus on the steric effect of alpha- and beta-substituents. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：134 / 137
页数：4
相关论文
共 37 条
  • [21] Anthracene-styrene-substitutedm-carborane derivatives: insights into the electronic and structural effects of substituents on photoluminescence
    Chaari, Mahdi
    Kelemen, Zsolt
    Choquesillo-Lazarte, Duane
    Teixidor, Francesc
    Vinas, Clara
    Nunez, Rosario
    INORGANIC CHEMISTRY FRONTIERS, 2020, 7 (12) : 2370 - 2380
  • [22] Bioproduction of Chiral Epoxyalkanes using Styrene Monooxygenase from Rhodococcus sp ST-10 (RhSMO)
    Toda, Hiroshi
    Imae, Ryouta
    Itoh, Nobuya
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (16) : 3443 - 3450
  • [23] Preparation and biochemical characterization of mutations in the active site of styrene monooxygenase from Pseudomonas putida (S12)
    Chandrasekaran, Priyanka
    Gassner, George
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 241
  • [24] Multicore Artificial Metalloenzymes Derived from Acylated Proteins as Catalysts for the Enantioselective Dihydroxylation and Epoxidation of Styrene Derivatives
    Leurs, Melanie
    Dorn, Bjoern
    Wilhelm, Sascha
    Manisegaran, Magiliny
    Tiller, Joerg. C.
    CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (42) : 10859 - 10867
  • [25] CATALYTIC AND ASYMMETRIC EPOXIDATION OF OLEFINS WITH IRON COMPLEXES OF TWIN-CORONET PORPHYRINS - A MECHANISTIC INSIGHT INTO THE CHIRAL INDUCTION OF STYRENE DERIVATIVES
    NARUTA, Y
    TANI, F
    ISHIHARA, N
    MARUYAMA, K
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (18) : 6865 - 6872
  • [26] Functional characterization of an (R)-selective styrene monooxygenase from streptomyces sp. NRRL S-31
    Cui, Can
    Guo, Chao
    Lin, Hui
    Ding, Zhao-Yun
    Liu, Yan
    Wu, Zhong-Liu
    ENZYME AND MICROBIAL TECHNOLOGY, 2020, 132
  • [27] Asymmetric Epoxidation of Styrene on the Heterogenized Chiral Salen Complexes Prepared from Organo-Functionalized Mesoporous Materials
    Dae-Woon Park
    Sung-Dae Choi
    Soon-Ja Choi
    Chung-Young Lee
    Geon-Joong Kim
    Catalysis Letters, 2002, 78 : 145 - 151
  • [28] Asymmetric epoxidation of styrene on the heterogenized chiral salen complexes prepared from organo-functionalized mesoporous materials
    Park, DW
    Choi, SD
    Choi, SJ
    Lee, CY
    Kim, GJ
    CATALYSIS LETTERS, 2002, 78 (1-4) : 145 - 151
  • [29] ASYMMETRIC EPOXIDATION OF ALLYL ALCOHOL DERIVATIVES BY OMEGA-HYDROXYLASE FROM PSEUDOMONAS-OLEOVORANS
    FU, H
    SHEN, GJ
    WONG, CH
    RECUEIL DES TRAVAUX CHIMIQUES DES PAYS-BAS-JOURNAL OF THE ROYAL NETHERLANDS CHEMICAL SOCIETY, 1991, 110 (05): : 167 - 170
  • [30] Catalytic and asymmetric epoxidation of olefins with iron complexes of 'twin-coronet' porphyrins. A mechanistic insight into the chiral induction of styrene derivatives
    1600, (113):
1234