Microbiological transformations 40. Use of fungal epoxide hydrolases for the synthesis of enantiopure alkyl epoxides

被引:33
作者
Moussou, P [1 ]
Archelas, A [1 ]
Furstoss, R [1 ]
机构
[1] Univ Mediterranee, ERS 157, Grp Biocatalyse & Chim, Fac Sci Luminy, F-13288 Marseille 9, France
关键词
D O I
10.1016/S0040-4020(97)10394-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The enantioselective biohydrolyses of various substituted alkyl-epoxides using seven different fungi are described These strains were used to achieve the preparation of these alkyl epoxides in high enantiomeric purity. A combined chemoenzymatic process is also described, allowing to enhance the overall yield of such an approach. (C) 1998 Elsevier Science Ltd. All rights reserved.
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收藏
页码:1563 / 1572
页数:10
相关论文
共 29 条
[1]  
[Anonymous], CATALYTIC ASYMMETRIC
[2]   Synthesis of enantiopure epoxides through biocatalytic approaches [J].
Archelas, A ;
Furstoss, R .
ANNUAL REVIEW OF MICROBIOLOGY, 1997, 51 :491-525
[3]   A new ligand class for the asymmetric dihydroxylation of olefins [J].
Becker, H ;
Sharpless, KB .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (04) :448-451
[4]  
BELRHLID R, 1992, BIOCATALYSIS, V6, P319
[5]   CHEMICAL AND BIOLOGICAL SYNTHESIS OF CHIRAL EPOXIDES [J].
BESSE, P ;
VESCHAMBRE, H .
TETRAHEDRON, 1994, 50 (30) :8885-8927
[6]   CHEMOENZYMATIC SYNTHESIS OF ALPHA-BICHIRAL SYNTHONS - APPLICATION TO THE PREPARATION OF CHIRAL EPOXIDES [J].
BESSE, P ;
VESCHAMBRE, H .
TETRAHEDRON-ASYMMETRY, 1993, 4 (06) :1271-1285
[7]   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
[8]   MICROBIOLOGICAL TRANSFORMATIONS .27. THE 1ST EXAMPLES FOR PREPARATIVE-SCALE ENANTIOSELECTIVE OR DIASTEREOSELECTIVE EPOXIDE HYDROLYZES USING MICROORGANISMS - AN UNEQUIVOCAL ACCESS TO ALL 4 BISABOLOL STEREOISOMERS [J].
CHEN, XJ ;
ARCHELAS, A ;
FURSTOSS, R .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (20) :5528-5532
[9]   DIMETHYLOXOSULFONIUM METHYLIDE ((CH3)2SOCH2) AND DIMETHYLSULFONIUM METHYLIDE ((CH3)2SCH2) FORMATION AND APPLICATION TO ORGANIC SYNTHESIS [J].
COREY, EJ ;
CHAYKOVSKY, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (06) :1353-+
[10]   BIOFORMATION OF OPTICALLY PURE EPOXIDES [J].
DEBONT, JAM .
TETRAHEDRON-ASYMMETRY, 1993, 4 (06) :1331-1340