LIPASE-CATALYZED ENANTIOSELECTIVE ACIDOLYSIS OF CHIRAL 2-METHYLALKANOATES

被引:14
作者
ENGEL, KH
机构
[1] Institut für Biotechnologie, Fachgebiet Chemisch-Technische Analyse, Technische Universität Berlin, Berlin, D-1000
关键词
ACIDOLYSIS; CHIRALITY; ENANTIOSELECTIVITY; ESTERIFICATION; KINETIC RESOLUTION; LIPASE; 2-METHYLALKANOATES; TRANSESTERIFICATION;
D O I
10.1007/BF02540565
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Lipase from Candida cylindracea catalyzes the acidolysis between racemic 2-methylalkanoates and fatty acids in heptane with a preference for the (S)-configurated esters. Velocity and enantioselectivity of the acyl transfer are strongly influenced by the structures of the initial substrates. The potential of this strategy for kinetic resolution of the enantiomers of chiral 2-methylalkanoates is demonstrated. Limitations of the procedure due to the reversible character of the reaction are discussed.
引用
收藏
页码:146 / 150
页数:5
相关论文
共 29 条
[1]  
[Anonymous], 1990, BIOCATAL BIOTRANSFOR
[2]   ISOCYANATES AS UNIVERSAL REAGENTS FOR THE FORMATION OF DERIVATIVES FOR GAS-CHROMATOGRAPHIC ENANTIOMER SEPARATION [J].
BENECKE, I ;
KONIG, WA .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1982, 21 (09) :709-709
[3]   QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTION OF ENANTIOMERS .2. ENZYME-CATALYZED ESTERIFICATIONS IN WATER ORGANIC-SOLVENT BIPHASIC SYSTEMS [J].
CHEN, CS ;
WU, SH ;
GIRDAUKAS, G ;
SIH, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (09) :2812-2817
[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]   ENZYMATIC CATALYSIS IN MONOPHASIC ORGANIC-SOLVENTS [J].
DORDICK, JS .
ENZYME AND MICROBIAL TECHNOLOGY, 1989, 11 (04) :194-211
[6]   LIPASE-CATALYZED REACTIONS OF CHIRAL HYDROXYACID ESTERS - COMPETITION OF ESTERIFICATION AND TRANSESTERIFICATION [J].
ENGEL, KH ;
BOHNEN, M ;
DOBE, M .
ENZYME AND MICROBIAL TECHNOLOGY, 1991, 13 (08) :655-660
[7]  
ENGEL KH, 1990, FLAVOUR SCIENCE AND TECHNOLOGY, P41
[8]   LIPASE-CATALYZED ENANTIOSELECTIVE ESTERIFICATION OF 2-METHYLALKANOIC ACIDS [J].
ENGEL, KH .
TETRAHEDRON-ASYMMETRY, 1991, 2 (03) :165-168
[9]   LIPASE-CATALYZED ESTER EXCHANGE-REACTIONS IN ORGANIC MEDIA WITH CONTROLLED HUMIDITY [J].
GODERIS, HL ;
AMPE, G ;
FEYTEN, MP ;
FOUWE, BL ;
GUFFENS, WM ;
VANCAUWENBERGH, SM ;
TOBBACK, PP .
BIOTECHNOLOGY AND BIOENGINEERING, 1987, 30 (02) :258-266
[10]   ASYMMETRIC TRANSFORMATIONS CATALYZED BY ENZYMES IN ORGANIC-SOLVENTS [J].
KLIBANOV, AM .
ACCOUNTS OF CHEMICAL RESEARCH, 1990, 23 (04) :114-120