Evaluation of deep eutectic solvent-water binary mixtures for lipase-catalyzed lipophilization of phenolic acids

被引:156
作者
Durand, Erwann [1 ]
Lecomte, Jerome [1 ]
Barea, Bruno [1 ]
Dubreucq, Eric [2 ]
Lortie, Robert [3 ]
Villeneuve, Pierre [1 ]
机构
[1] CIRAD, UMR IATE 1208, F-34398 Montpellier, France
[2] Montpellier SupAgro, UMR IATE 1208, F-34060 Montpellier, France
[3] Natl Res Council Canada, Montreal, PQ H4P 2R2, Canada
关键词
ENZYMATIC-SYNTHESIS; CANDIDA-ANTARCTICA; ESTERIFICATION; GLYCEROL; MEDIA; DERIVATIVES; BENIGN;
D O I
10.1039/c3gc40899j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This work reports the first lipase-catalyzed reactions between substrates of different polarities using deep eutectic solvents as a medium. The model reaction consisted of a lipophilization process based on the alcoholysis of phenolic esters using immobilized Candida antarctica lipase B as a biocatalyst. Results showed that water could dramatically improve the lipase activity and change the reactivity of phenolic substrates. Indeed, very low conversions (<2%) were observed in pure DES, whereas in DES-water binary mixtures, quantitative conversions were achieved. After investigating the role of various parameters, such as the substrate concentration and ratio, pH or thermodynamic activity of water, the effect of the presence of water in pure DES based on urea or glycerol was discussed. In this paper, we propose new perspectives for the enzymatic modification of polar substrates using this novel generation of green, inexpensive and easy-to-handle solvents.
引用
收藏
页码:2275 / 2282
页数:8
相关论文
共 30 条
[1]   Eutectic salts promote green synthesis of bis(indolyl) methanes [J].
Azizi, Najmadin ;
Manocheri, Zohreh .
RESEARCH ON CHEMICAL INTERMEDIATES, 2012, 38 (07) :1495-1500
[2]   Enzymatic esterifications of functionalized phenols for the synthesis of lipophilic antioxidants [J].
Buisman, GJH ;
van Helteren, CTW ;
Kramer, GFH ;
Veldsink, JW ;
Derksen, JTP ;
Cuperus, FP .
BIOTECHNOLOGY LETTERS, 1998, 20 (02) :131-136
[3]   Novel Bronsted acidic deep eutectic solvent as reaction media for esterification of carboxylic acid with alcohols [J].
De Santi, Valerio ;
Cardellini, Fabio ;
Brinchi, Lucia ;
Germani, Raimondo .
TETRAHEDRON LETTERS, 2012, 53 (38) :5151-5155
[4]   Evaluation of deep eutectic solvents as new media for Candida antarctica B lipase catalyzed reactions [J].
Durand, E. ;
Lecomte, J. ;
Barea, B. ;
Piombo, G. ;
Dubreucq, E. ;
Villeneuve, P. .
PROCESS BIOCHEMISTRY, 2012, 47 (12) :2081-2089
[5]   Phenolic acids enzymatic lipophilization [J].
Figueroa-Espinoza, MC ;
Villeneuve, P .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2005, 53 (08) :2779-2787
[6]   Lipase-catalyzed glucose fatty acid ester synthesis in ionic liquids [J].
Ganske, F ;
Bornscheuer, UT .
ORGANIC LETTERS, 2005, 7 (14) :3097-3098
[7]   Hydrolase-catalyzed biotransformations in deep eutectic solvents [J].
Gorke, Johnathan T. ;
Srienc, Friedrich ;
Kazlauskas, Romas J. .
CHEMICAL COMMUNICATIONS, 2008, (10) :1235-1237
[8]   Freeze-Drying of Aqueous Solutions of Deep Eutectic Solvents: A Suitable Approach to Deep Eutectic Suspensions of Self-Assembled Structures [J].
Gutierrez, Maria C. ;
Ferrer, Maria L. ;
Reyes Mateo, C. ;
del Monte, Francisco .
LANGMUIR, 2009, 25 (10) :5509-5515
[9]   Esterification of phenolic acids from green coffee with an immobilized lipase from Candida antarctica in solvent-free medium [J].
Guyot, B ;
Bosquette, B ;
Pina, M ;
Graille, J .
BIOTECHNOLOGY LETTERS, 1997, 19 (06) :529-532
[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