Pseudomonas cepacia lipase catalyzed esterification and transesterification of 3-(furan-2-yl) propanoic acid/ethyl ester: A comparison in ionic liquids vs hexane

被引:16
作者
Vidya, P. [1 ]
Chadha, Anju [1 ,2 ]
机构
[1] Indian Inst Technol, Bioorgan Chem Lab, Dept Biotechnol, Madras 600036, Tamil Nadu, India
[2] Indian Inst Technol, Natl Ctr Catalysis Res, Madras 600036, Tamil Nadu, India
关键词
Ionic liquids; Esterification; Transesterification; Pseudomonas cepacia lipase; 3-(Furan-2-yl) propanoic acid ester; TRIACYLGLYCEROL LIPASE; ENZYMATIC CATALYSIS; KINETIC RESOLUTION; CRYSTAL-STRUCTURE; TEMPERATURE; STABILIZATION; BIOCATALYSIS; REVEALS; ANION;
D O I
10.1016/j.molcatb.2010.01.032
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
A comparison of the Pseudomonas cepacia lipase (lipase PS) catalyzed esterification of 3-(furan-2-yl) propanoic acid and transesterification of ethyl 3-(furan-2-yl) propanoate with six straight chain alcohols (propanol to octanol) in ionic liquids and hexane was carried out. The ionic liquids selected, [Bmim]BF4, [Bmim]PF6, and [Bmim]Tf2N, consisted clan identical cation and different anions. This is the first report on the biocatalyzed synthesis of these esters. In all the media, lipase PS catalyzed esterification of 3-(furan-2-yl) propanoic acid resulted in high yields of the esters compared to the transesterification of ethyl 3-(furan-2-yl) propanoate.[Bmim]Tf2N proved to be the best: yielding 98-67% of the product by lipase PS catalyzed esterification. The lipase PS-[Bmim]Tf2N and lipase PS-[Bmim]PF6 mixture was recycled five times without any decrease in the yields of the products and was found to be operationally stable up to 10 months at room temperature. (C) 2010 Elsevier B.V. All rights reserved.
引用
收藏
页码:68 / 72
页数:5
相关论文
共 36 条
[1]   How Hofmeister ion interactions affect protein stability [J].
Baldwin, RL .
BIOPHYSICAL JOURNAL, 1996, 71 (04) :2056-2063
[2]   Hofmeister effect on enzymatic catalysis and colloidal structures [J].
Bauduin, P ;
Renoncourt, A ;
Touraud, D ;
Kunz, W ;
Ninham, BW .
CURRENT OPINION IN COLLOID & INTERFACE SCIENCE, 2004, 9 (1-2) :43-47
[3]   Specific anion effects on enzymatic activity in nonaqueous media [J].
Bilanicova, Dagmar ;
Salis, Andrea ;
Ninham, Barry W. ;
Monduzzi, Maura .
JOURNAL OF PHYSICAL CHEMISTRY B, 2008, 112 (38) :12066-12072
[4]   Dynamic kinetic resolution of racemic N-phthalyl amino acids using (S)-α-methylpantolactone as the chiral auxiliary [J].
Calmes, M ;
Glot, C ;
Michel, T ;
Rolland, M ;
Martinez, J .
TETRAHEDRON-ASYMMETRY, 2000, 11 (03) :737-741
[5]   Understanding structure -: Stability relationships of Candida antartica lipase B in ionic liquids [J].
De Diego, T ;
Lozano, P ;
Gmouh, S ;
Vaultier, M ;
Iborra, JL .
BIOMACROMOLECULES, 2005, 6 (03) :1457-1464
[6]   Fluorescence and CD spectroscopic analysis of the α-chymotrypsin stabilization by the ionic liquid, 1-ethyl-3-methylimidazolium bis[(trifluoromethyl)sulfonyl]amide [J].
De Diego, T ;
Lozano, P ;
Gmouh, S ;
Vaultier, M ;
Iborra, JL .
BIOTECHNOLOGY AND BIOENGINEERING, 2004, 88 (07) :916-924
[7]   Enzymatic catalysis of formation of Z-aspartame in ionic liquid -: An alternative to enzymatic catalysis in organic solvents [J].
Erbeldinger, M ;
Mesiano, AJ ;
Russell, AJ .
BIOTECHNOLOGY PROGRESS, 2000, 16 (06) :1129-1131
[8]   Surface tensions of imidazolium based ionic liquids: Anion, cation, temperature and water effect [J].
Freire, Mara G. ;
Carvalho, Pedro J. ;
Fernandes, Ana M. ;
Marrucho, Isabel M. ;
Queimada, Antonio J. ;
Coutinho, Joao A. P. .
JOURNAL OF COLLOID AND INTERFACE SCIENCE, 2007, 314 (02) :621-630
[9]   Fine-tuning furan toxicity: fast and quantitative DNA interchain crosslink formation upon selective oxidation of a furan containing oligonucleotide [J].
Halila, S ;
Velasco, T ;
De Clercq, P ;
Madder, A .
CHEMICAL COMMUNICATIONS, 2005, (07) :936-938
[10]   Characterization and comparison of hydrophilic and hydrophobic room temperature ionic liquids incorporating the imidazolium cation [J].
Huddleston, JG ;
Visser, AE ;
Reichert, WM ;
Willauer, HD ;
Broker, GA ;
Rogers, RD .
GREEN CHEMISTRY, 2001, 3 (04) :156-164