Non-covalent modification of the active site of cytochrome P450 for inverting the stereoselectivity of monooxygenation

被引：18
|
作者：
Fujishiro, Takashi [1 ]
Shoji, Osami [1 ]
Watanabe, Yoshihito [1 ,2 ]
机构：
[1] Nagoya Univ, Grad Sch Sci, Dept Chem, Chikusa Ku, Nagoya, Aichi 4648602, Japan
[2] Nagoya Univ, Res Ctr Mat Sci, Chikusa Ku, Nagoya, Aichi 4648602, Japan
来源：
TETRAHEDRON LETTERS | 2011年 / 52卷 / 03期
关键词：
Cytochrome P450; Stereoselectivity; Sulfoxidation; Protein modification; Hydrogen peroxide; Biocatalyst; BACILLUS-SUBTILIS; SUBSTRATE RECOGNITION; ENANTIOSELECTIVITY; LIPASE; INVERSION; MUTATION; ENZYMES;
D O I：
10.1016/j.tetlet.2010.11.048
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The enantioselectivity in the sulfoxidation of thioanisole catalyzed by cytochrome P450(BS beta) with a decoy molecule, a dummy molecule of the natural substrate, can be inverted by changing the structure of the decoy molecule. The methodology demonstrated herein shows the potential for controlling the stereoselectivity of biocatalysts without any mutagenesis. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码：395 / 397
页数：3
相关论文
共 50 条
  • [1] Synthetic models for the active site of cytochrome P450
    Tani, F
    Matsu-ura, M
    Nakayama, S
    Naruta, Y
    COORDINATION CHEMISTRY REVIEWS, 2002, 226 (1-2) : 219 - 226
  • [2] Progress in cytochrome P450 active site modeling
    Kemp, CA
    Maréchal, JD
    Sutcliffe, MJ
    ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 2005, 433 (02) : 361 - 368
  • [3] Modification of the heme active site to increase the peroxidase activity of thermophilic cytochrome P450: A rational approach
    Behera, Rabindra Kumar
    Goyal, Sandeep
    Mazumdar, Shyamalava
    JOURNAL OF INORGANIC BIOCHEMISTRY, 2010, 104 (11) : 1185 - 1194
  • [4] Structural Design of the Active Site for Covalent Attachment of the Heme to the Protein Matrix: Studies on a Thennostable Cytochrome P450
    Goyal, Sandeep
    Deshpande, Megha S.
    Mazumdar, Shyamalava
    BIOCHEMISTRY, 2011, 50 (06) : 1042 - 1052
  • [5] Photoaffinity ligands in the study of cytochrome p450 active site structure
    Gartner, CA
    CURRENT MEDICINAL CHEMISTRY, 2003, 10 (08) : 671 - 689
  • [6] Theoretical study on compound I formation in monooxygenation mechanism by cytochrome P450
    Hata, M
    Hirano, Y
    Hoshino, T
    Nishida, R
    Tsuda, M
    JOURNAL OF PHYSICAL CHEMISTRY B, 2004, 108 (30): : 11189 - 11195
  • [7] Steroid hydroxylations: A paradigm for cytochrome P450 catalyzed mammalian monooxygenation reactions
    Estabrook, RW
    BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 2005, 338 (01) : 290 - 298
  • [8] Stereoselectivity of Human Cytochrome P450 in Metabolic and Inhibitory Activities
    Niwa, Toshiro
    Murayama, Norie
    Yamazaki, Hiroshi
    CURRENT DRUG METABOLISM, 2011, 12 (06) : 549 - 569
  • [9] Regulation of cytochrome P450 by posttranslational modification
    Aguiar, M
    Masse, R
    Gibbs, BF
    DRUG METABOLISM REVIEWS, 2005, 37 (02) : 379 - 404
  • [10] Profiling the Cytochrome P450 2J2 Active Site
    Motl, Nicole
    Smith, Richard D.
    Carlson, Heather A.
    Scott, Emily E.
    FASEB JOURNAL, 2022, 36
12345