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

被引:19
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
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 34 条
[1]   Complete inversion of enantioselectivity towards acetylated tertiary alcohols by a double mutant of a Bacillus subtilis esterase [J].
Bartsch, Sebastian ;
Kourist, Robert ;
Bornscheuer, Uwe T. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (08) :1508-1511
[2]   Role of sulfur chirality in the chemical processes of biology [J].
Bentley, R .
CHEMICAL SOCIETY REVIEWS, 2005, 34 (07) :609-624
[3]   Cytochromes P450 as versatile biocatalysts [J].
Bernhardt, Rita .
JOURNAL OF BIOTECHNOLOGY, 2006, 124 (01) :128-145
[4]   APPLICATIONS OF SULFOXIDES TO ASYMMETRIC-SYNTHESIS OF BIOLOGICALLY-ACTIVE COMPOUNDS [J].
CARRENO, MC .
CHEMICAL REVIEWS, 1995, 95 (06) :1717-1760
[5]   Structure and chemistry of cytochrome P450 [J].
Denisov, IG ;
Makris, TM ;
Sligar, SG ;
Schlichting, I .
CHEMICAL REVIEWS, 2005, 105 (06) :2253-2277
[6]   Preparative use of isolated CYP102 monooxygenases -: A critical appraisal [J].
Eiben, Sabine ;
Kaysser, Leonard ;
Maurer, Steffen ;
Kuehnel, Katja ;
Urlacher, Vlada B. ;
Schmid, Rolf D. .
JOURNAL OF BIOTECHNOLOGY, 2006, 124 (04) :662-669
[7]   Recent developments in the synthesis and utilization of chiral sulfoxides [J].
Fernández, I ;
Khiar, N .
CHEMICAL REVIEWS, 2003, 103 (09) :3651-3705
[8]   Cytochrome P450 enzymes in the generation of commercial products [J].
Guengerich, FP .
NATURE REVIEWS DRUG DISCOVERY, 2002, 1 (05) :359-366
[9]   Inverting enantio selectivity of Burkholderia gladioli esterase EstB by directed and designed evolution [J].
Ivancic, Mirela ;
Valinger, Goran ;
Gruber, Karl ;
Schwab, Helmut .
JOURNAL OF BIOTECHNOLOGY, 2007, 129 (01) :109-122
[10]   Kinetic characterization of Compound I formation in the thermostable cytochrome P450 CYP119 [J].
Kellner, DG ;
Hung, SC ;
Weiss, KE ;
Sligar, SG .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2002, 277 (12) :9641-9644