Optimization of lipase-catalyzed glucose fatty acid ester synthesis in a two-phase system containing ionic liquids and t-BuOH

被引:104
作者
Ganske, F [1 ]
Bornscheuer, UT [1 ]
机构
[1] Univ Greifswald, Dept Tech Chem & Biotechnol, Inst Chem & Biochem, D-17487 Greifswald, Germany
关键词
sugar ester; ionic liquid; CAL-13; two-phase system; enzymatic synthesis;
D O I
10.1016/j.molcatb.2005.08.004
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
Selective lipase-catalyzed synthesis of glucose fatty acid esters in two-phase systems consisting of an ionic liquid (1-butyl-3-methyl imidazolium tetrafluoroborate [BMIM][BF4] or 1-butyl-3-methyl imidazolium hexafluorophosphate [BMIM][PF6]) and t-butanol as organic solvent was investigated. The best enzyme was commercially available lipase B from Candida antarctica (CAL-B), but also lipase from Thermomyces lanuginosa (TLL) gave good conversion. After thorough optimization of several reaction conditions (chain-length and type of acyl donor, temperature, reaction time, percentage of co-solvent) conversions up to 60% could be achieved using fatty acid vinyl ester as acyl donors in [BMIM] [PF6] in the presence of 40% t-BuOH with CAL-B at 60 degrees C. (c) 2005 Elsevier B.V. All rights reserved.
引用
收藏
页码:40 / 42
页数:3
相关论文
共 12 条
[1]   One biocatalyst - Many applications: The use of Candida antarctica B-lipase in organic synthesis [J].
Anderson, EM ;
Karin, M ;
Kirk, O .
BIOCATALYSIS AND BIOTRANSFORMATION, 1998, 16 (03) :181-204
[2]   THE FUTURE-IMPACT OF INDUSTRIAL LIPASES [J].
BJORKLING, F ;
GODTFREDSEN, SE ;
KIRK, O .
TRENDS IN BIOTECHNOLOGY, 1991, 9 (10) :360-363
[3]  
Cao LQ, 1996, FETT-LIPID, V98, P332
[4]   Optimization of carbohydrate fatty acid ester synthesis in organic media by a lipase from Candida antarctica [J].
Degn, P ;
Zimmermann, W .
BIOTECHNOLOGY AND BIOENGINEERING, 2001, 74 (06) :483-491
[5]   Synthesis of sugar esters in solvent mixtures by lipases from Thermomyces lanuginosus and Candida antarctica B, and their antimicrobial properties [J].
Ferrer, M ;
Soliveri, J ;
Plou, FJ ;
López-Cortés, N ;
Reyes-Duarte, D ;
Christensen, M ;
Copa-Patiño, JL ;
Ballesteros, A .
ENZYME AND MICROBIAL TECHNOLOGY, 2005, 36 (04) :391-398
[6]   Lipase-catalyzed glucose fatty acid ester synthesis in ionic liquids [J].
Ganske, F ;
Bornscheuer, UT .
ORGANIC LETTERS, 2005, 7 (14) :3097-3098
[7]   Enzymatic selective acylation of glycosides in ionic liquids: significantly enhanced reactivity and regioselectivity [J].
Kim, MJ ;
Choi, MY ;
Lee, JK ;
Ahn, Y .
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2003, 26 (3-6) :115-118
[8]   Enzyme catalysis in ionic liquids [J].
Kragl, U ;
Eckstein, M ;
Kaftzik, N .
CURRENT OPINION IN BIOTECHNOLOGY, 2002, 13 (06) :565-571
[9]   Lipase-catalyzed reactions in ionic liquids [J].
Lau, RM ;
van Rantwijk, F ;
Seddon, KR ;
Sheldon, RA .
ORGANIC LETTERS, 2000, 2 (26) :4189-4191
[10]   Improved preparation and use of room-temperature ionic liquids in lipase-catalyzed enantio- and regioselective acylations [J].
Park, S ;
Kazlauskas, RJ .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (25) :8395-8401