Biocatalytic resolution of 2-methyl-2-(aryl)alkyloxiranes using novel bacterial epoxide hydrolases

被引:58
作者
Osprian, I [1 ]
Kroutil, W [1 ]
Mischitz, M [1 ]
Faber, K [1 ]
机构
[1] GRAZ UNIV TECHNOL,INST ORGAN CHEM,A-8010 GRAZ,AUSTRIA
关键词
D O I
10.1016/S0957-4166(96)00493-4
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Biocatalytic resolution of alkyl- and (arylalkyl)-oxiranes was accomplished by employing the epoxide hydrolase activity of lyophilized whole cells of seven bacterial strains belonging to the genera Rhodococcus, Mycobacterium and Nocardia. Whereas no suitable biocatalyst was found for 1-octene oxide, excellent selectivities were obtained with 2-methyl-2-substituted epoxides bearing an alkyl- or (aryl)alkyl side chain. (C) 1997, Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:65 / 71
页数:7
相关论文
共 39 条
[1]  
Abraham W.-R., 1990, J ESSENT OIL RES, V2, P251, DOI [10.1080/10412905.1990.9697876, DOI 10.1080/10412905.1990.9697876]
[2]   Carboxylation of epoxides to beta-keto acids in cell extracts of Xanthobacter strain Py2 [J].
Allen, JR ;
Ensign, SA .
JOURNAL OF BACTERIOLOGY, 1996, 178 (05) :1469-1472
[3]   A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS [J].
CARLSEN, PHJ ;
KATSUKI, T ;
MARTIN, VS ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) :3936-3938
[4]   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
[5]  
DALTON H, 1980, ADV APPL MICROBIOL, V26, P71
[6]   THE METABOLISM OF 1,2-PROPANEDIOL BY THE PROPYLENE-OXIDE UTILIZING BACTERIUM NOCARDIA-A60 [J].
DEBONT, JAM ;
VANDIJKEN, JP ;
VANGINKEL, KG .
BIOCHIMICA ET BIOPHYSICA ACTA, 1982, 714 (03) :465-470
[7]   BIOFORMATION OF OPTICALLY PURE EPOXIDES [J].
DEBONT, JAM .
TETRAHEDRON-ASYMMETRY, 1993, 4 (06) :1331-1340
[8]   PRACTICAL APPROACH TO HIGH-YIELD ENZYMATIC STEREOSPECIFIC ORGANIC-SYNTHESIS IN MULTIPHASE SYSTEMS [J].
DESMET, MJ ;
WITHOLT, B ;
WYNBERG, H .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (15) :3128-3131
[9]   Microbial epoxide hydrolases [J].
Faber, K ;
Mischitz, M ;
Kroutil, W .
ACTA CHEMICA SCANDINAVICA, 1996, 50 (03) :249-258
[10]  
FEBER K, 1996, ACTA CHEM SCAND, V50, P249