Oxidations catalyzed by phenylacetone monooxygenase from Thermobifida fusca

被引：71
作者：
de Gonzalo, G
Pazmiño, DET
Ottolina, G
Fraaije, MW
Carrea, G
机构：
[1] CNR, Ist Chim Riconoscimento Mol, I-20131 Milan, Italy
[2] Univ Groningen, Biochem Lab, Groningen Biomol Sci & Biotechnol Inst, NL-9747 AG Groningen, Netherlands
来源：
TETRAHEDRON-ASYMMETRY | 2005年 / 16卷 / 18期
关键词：
D O I：
10.1016/j.tetasy.2005.08.004
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Several organic sulfides, ketones and other organic systems have been tested as substrates in oxidation reactions catalyzed by the recently discovered phenylacetone monooxygenase from Thermobifida fusca. The biocatalytic properties of this Baeyer-Villiger monooxygenase have been studied, revealing reactivity with a large range of sulfides and ketones. Oxidations of several sulfoxides, an amine and an organoboron compound were also observed. The enzyme is able to oxidize a number of sulfides with excellent enantioselectivity, demonstrating the catalytic potential of this novel biocatalyst. (C) 2005 Elsevier Ltd. All rights reserved.
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页码：3077 / 3083
页数：7
相关论文
共 49 条
[1]   Towards large-scale synthetic applications of Baeyer-Villiger monooxygenases [J].
Alphand, V ;
Carrea, G ;
Wohlgemuth, R ;
Furstoss, R ;
Woodley, JM .
TRENDS IN BIOTECHNOLOGY, 2003, 21 (07) :318-323
[2]  
ALPHAND V, 1995, BAEYER VILLIGER OXID, P745
[3]   INTRAMOLECULAR REACTIONS .11. CYCLIZATION OF OMEGA-HALOGENOALKYL SULFIDES - SIGNIFICANCE OF BROMIDE/CHLORIDE RATIOS IN DISPLACEMENT REACTIONS [J].
BIRD, R ;
STIRLING, CJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1973, (09) :1221-1226
[4]   Converting phenylacetone monooxygenase into phenylcyclohexanone monooxygenase by rational design: Towards practical Baeyer-Villiger monooxygenases [J].
Bocola, M ;
Schulz, F ;
Leca, F ;
Vogel, A ;
Fraaije, MW ;
Reetz, MT .
ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (7-8) :979-986
[5]   HIGHLY ENANTIOSELECTIVE OXIDATION OF SULFIDES MEDIATED BY A CHIRAL TITANIUM COMPLEX [J].
BRUNEL, JM ;
DITER, P ;
DUETSCH, M ;
KAGAN, HB .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (24) :8086-8088
[6]   QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTIONS OF ENANTIOMERS [J].
CHEN, CS ;
FUJIMOTO, Y ;
GIRDAUKAS, G ;
SIH, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (25) :7294-7299
[7]   Enantioselective oxidation of sulfides to sulfoxides catalysed by bacterial cyclohexanone monooxygenases [J].
Colonna, S ;
Gaggero, N ;
Pasta, P ;
Ottolina, G .
CHEMICAL COMMUNICATIONS, 1996, (20) :2303-2307
[8]   CHLOROPEROXIDASE AND HYDROGEN-PEROXIDE - AN EFFICIENT SYSTEM FOR ENZYMATIC ENANTIOSELECTIVE SULFOXIDATIONS [J].
COLONNA, S ;
GAGGERO, N ;
CASELLA, L ;
CARREA, G ;
PASTA, P .
TETRAHEDRON-ASYMMETRY, 1992, 3 (01) :95-106
[9]   ENANTIOSELECTIVE OXIDATIONS OF SULFIDES CATALYZED BY CHLOROPEROXIDASE [J].
COLONNA, S ;
GAGGERO, N ;
MANFREDI, A ;
CASELLA, L ;
GULLOTTI, M ;
CARREA, G ;
PASTA, P .
BIOCHEMISTRY, 1990, 29 (46) :10465-10468
[10]  
CROOKS PA, 1988, CHEM IND-LONDON, P95
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