Enhanced enantioselectivity of Candida rugosa lipase in ionic liquids as compared to organic solvents

被引:72
作者
Ulbert, O [1 ]
Fráter, T [1 ]
Bélafi-Bakó, K [1 ]
Gubicza, L [1 ]
机构
[1] Univ Veszprem, Chem Proc Engn Res Inst, H-8201 Veszprem, Hungary
基金
匈牙利科学研究基金会;
关键词
ionic liquid; Candida rugosa lipase; enantioselective esterification; water activity; hydrophobicity;
D O I
10.1016/j.molcatb.2004.07.003
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Candida rugosa lipase has shown to retain catalytic activity in ionic liquids. In this work, enantioselectivity of this enzyme in the esterific action of 2-substituted-propanoic acids and 1-butanol is compared in ionic liquids and organic solvents. The role of solvent hydrophobicity (log P), water content and the effect of substituents are evaluated. Optimal water concentration in the reaction media was determined, where the enzyme shows maximal activity and enantioselectivity. Enantioselectivity can be improved when chlorine substituent was replaced by slightly bigger size bromine. Contrary to reactions in common organic solvents, there was no need for purification steps following the reaction in ionic liquids in order to recycle the enzyme. In 1-butyl-3-methyl-inidazolium-hexafluoro-phosphate ([bmim]PF6) and 1-octyl-3-nDnylimidazohum-hexafiuoro-phosphate ([onim]PF6) ionic liquids, C. rugosa lipase could be recycled five times without appreciable activity or enantioselectivity losses. (C) 2004 Elsevier B.V All rights reserved.
引用
收藏
页码:39 / 45
页数:7
相关论文
共 25 条
[1]   Application of pervaporation for removal of water produced during enzymatic esterification in ionic liquids [J].
Bélafi-Bakó, K ;
Dörmo, N ;
Ulbert, O ;
Gubicza, L .
DESALINATION, 2002, 149 (1-3) :267-268
[2]  
BELAFIBAKO K, 2001, P ENG MEMBRANES, V1, P287
[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]   Lipase-catalyzed enantioselective esterification of ibuprofen in organic solvents under controlled water activity [J].
Ducret, A ;
Trani, M ;
Lortie, R .
ENZYME AND MICROBIAL TECHNOLOGY, 1998, 22 (04) :212-216
[5]   Enhanced enantioselectivity of lipase from Pseudomonas sp at high temperatures and fixed water activity in the ionic liquid, 1-butyl-3-methylimidazolium bis[(trifluoromethyl)sulfonyl]amide [J].
Eckstein, M ;
Wasserscheid, P ;
Kragl, U .
BIOTECHNOLOGY LETTERS, 2002, 24 (10) :763-767
[6]   HOW CAN THE SOLVENT AFFECT ENZYME ENANTIOSELECTIVITY [J].
FITZPATRICK, PA ;
KLIBANOV, AM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (08) :3166-3171
[7]   New developments in catalysis using ionic liquids [J].
Gordon, CM .
APPLIED CATALYSIS A-GENERAL, 2001, 222 (1-2) :101-117
[8]   Enzymatic esterification in ionic liquids integrated with pervaporation for water removal [J].
Gubicza, L ;
Nemestóthy, N ;
Fráter, T ;
Bélafi-Bakó, K .
GREEN CHEMISTRY, 2003, 5 (02) :236-239
[9]   EFFECT OF WATER-MIMICKING ADDITIVES ON THE SYNTHETIC ACTIVITY AND ENANTIOSELECTIVITY IN ORGANIC-SOLVENTS OF A CANDIDA-CYLINDRACEA LIPASE [J].
GUBICZA, L ;
KELEMENHORVATH, I .
JOURNAL OF MOLECULAR CATALYSIS, 1993, 84 (01) :L27-L32
[10]   THERMODYNAMIC PREDICTIONS FOR BIOCATALYSIS IN NONCONVENTIONAL MEDIA - THEORY, TESTS, AND RECOMMENDATIONS FOR EXPERIMENTAL-DESIGN AND ANALYSIS [J].
HALLING, PJ .
ENZYME AND MICROBIAL TECHNOLOGY, 1994, 16 (03) :178-206