ASYMMETRIC OXIDATION OF SULFIDES BY CYCLOHEXANONE MONOOXYGENASE

被引:36
作者
SECUNDO, F
CARREA, G
DALLAVALLE, S
FRANZOSI, G
机构
[1] CNR,IST CHIM ORMONI,VIA MARIO BIANCO 9,I-20131 MILAN,ITALY
[2] CTR CNR,DIPARTIMENTO CHIM ORGAN & IND,MILAN,ITALY
[3] IST DONEGANI SPA,I-28100 NOVARA,ITALY
关键词
D O I
10.1016/S0957-4166(00)82244-2
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Cyclohexanone monooxygenase catalyzes the asymmetric oxidazion of numerous alkyl aryl sulfides with the alkyl chain functionalyzed with Cl, CN, vinyl or hydroxy groups. Sulfoxides with enantiomeric excesses up to 99% were obtained. The structure of the sulfide markedly influenced enzyme enantioselectivity.
引用
收藏
页码:1981 / 1982
页数:2
相关论文
共 10 条
[1]   EFFECTS OF SUBSTRATE STRUCTURE ON THE ENANTIOSELECTIVITY AND STEREOCHEMICAL COURSE OF SULFOXIDATION CATALYZED BY CYCLOHEXANONE MONOOXYGENASE [J].
CARREA, G ;
REDIGOLO, B ;
RIVA, S ;
COLONNA, S ;
GAGGERO, N ;
BATTISTEL, E ;
BIANCHI, D .
TETRAHEDRON-ASYMMETRY, 1992, 3 (08) :1063-1068
[2]  
DIJKSTRA R, 1954, RECL TRAV CHIM PAY B, V73, P569
[3]  
DUNACH E, 1985, NOUV J CHIM, V9, P1
[4]   THE FISSION OF THE THIOETHER LINKAGE IN CERTAIN BETA-SULPHONYL-SULPHIDES [J].
FORDMOORE, AH ;
PETERS, RA ;
WAKELIN, RW .
JOURNAL OF THE CHEMICAL SOCIETY, 1949, (JUL) :1754-1757
[5]   THE LEWIS ACID-CATALYZED INTRAMOLECULAR ASYMMETRIC ENE REACTION USING A CHIRAL ALPHA-CYANOVINYLIC SULFOXIDE AS AN ENOPHILE [J].
HIROI, K ;
UMEMURA, M .
TETRAHEDRON, 1993, 49 (09) :1831-1840
[6]   REACTIONS OF MERCAPTANS WITH ACRYLIC AND METHACRYLIC DERIVATIVES [J].
HURD, CD ;
GERSHBEIN, LL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1947, 69 (10) :2328-2335
[7]   STUDIES ON THE CHIRALITY OF SULFOXIDATION CATALYZED BY BACTERIAL FLAVOENZYME CYCLOHEXANONE MONO-OXYGENASE AND HOG LIVER FLAVIN ADENINE-DINUCLEOTIDE CONTAINING MONO-OXYGENASE [J].
LIGHT, DR ;
WAXMAN, DJ ;
WALSH, C .
BIOCHEMISTRY, 1982, 21 (10) :2490-2498
[9]   ENZYMIC BAEYER-VILLIGER OXIDATIONS BY FLAVIN-DEPENDENT MONOOXYGENASES [J].
WALSH, CT ;
CHEN, YCJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (03) :333-343
[10]   ASYMMETRIC OXIDATION OF SULFIDES MEDIATED BY CHIRAL TITANIUM COMPLEXES - MECHANISTIC AND SYNTHETIC ASPECTS [J].
ZHAO, SH ;
SAMUEL, O ;
KAGAN, HB .
TETRAHEDRON, 1987, 43 (21) :5135-5144