The enhancement of enantioselectivities for lipase-catalyzed reactions by using carbamates

被引:11
作者
Lin, G [1 ]
Lin, WY [1 ]
Shieh, CT [1 ]
机构
[1] Natl Chung Hsing Univ, Dept Chem, Taichung 402, Taiwan
关键词
D O I
10.1016/S0040-4039(98)02021-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The enantioselectivity of porcine pancreatic lipase-catalyzed resolution of 1-indanol was enhanced up to 3 fold in the presence of carbamates. The optimum incubation time for 4-nitrophenyl-N-hexyl carbamate and the enzyme was 18 h before this biocatalytic resolution. The optimum concentration of the inhibitor 4-nitrophenyl-N-hexyl carbamate in this resolution was 1 % mole equivalent of the substrate 1-indanol. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:8881 / 8884
页数:4
相关论文
共 28 条
[1]  
Ammon R, 1931, BIOCHEM Z, V234, P54
[2]  
Bamann E, 1930, BER DTSCH CHEM GES, V63, P394, DOI 10.1002/cber.19300630223
[3]   GENERAL-ASPECTS AND OPTIMIZATION OF ENANTIOSELECTIVE BIOCATALYSIS IN ORGANIC-SOLVENTS - THE USE OF LIPASES [J].
CHEN, CS ;
SIH, CJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (06) :695-707
[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]  
DAVIES HG, 1989, BIOTRANSFORMATIONS P
[6]  
FABER K, 1992, BIOTRANSFORMATIONS O
[7]   ANALOGS OF REACTION INTERMEDIATES IDENTIFY A UNIQUE SUBSTRATE-BINDING SITE IN CANDIDA-RUGOSA LIPASE [J].
GROCHULSKI, P ;
BOUTHILLIER, F ;
KAZLAUSKAS, RJ ;
SERREQI, AN ;
SCHRAG, JD ;
ZIOMEK, E ;
CYGLER, M .
BIOCHEMISTRY, 1994, 33 (12) :3494-3500
[8]   ENANTIOSELECTIVE INHIBITION - A STRATEGY FOR IMPROVING THE ENANTIOSELECTIVITY OF BIOCATALYTIC SYSTEMS [J].
GUO, ZW ;
SIH, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (17) :6836-6841
[9]  
HOSIE L, 1987, J BIOL CHEM, V262, P260
[10]   Thiacrown ether technology in lipase-catalyzed reaction: Scope and limitation for preparing optically active 3-hydroxyalkanenitriles and application to insect pheromone synthesis [J].
Itoh, T ;
Mitsukura, K ;
Kanphai, W ;
Takagi, Y ;
Kihara, H ;
Tsukube, H .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (26) :9165-9172