[en] A screening of nine ionic liquids (ILs) has been carried out in order to study the influence of the anion's and cation's nature and structure on the synthesis of mannosyl myristate by (trans)esterification catalyzed by Novozym® 435. The best ILs in terms of yield (η) and initial rate (v0) are those based on the TFO- anion. The 24h yield (24h-η) reached 64.9% in [Bmim][TFO] and 70.9% in [Bmpyrr][TFO] by transesterification while it reached 29.7% and 44.5% respectively in each IL by esterification. [Bmpyrr][TFO] based on the pyrrolidinium cation gave the best results although this cation has been rarely used for biocatalysis. This work has thus highlighted a cation that could be further studied in biocatalysis of glycosylated compounds. The study of the relationship between the structure of the ILs and the v0 and η for the biocatalysis of mannosyl myristate showed that the lipase effectiveness is influenced by the anions while the cations have an indirect influence on the interaction strength between Novozym® 435 and the anions.
Disciplines :
Chemistry
Author, co-author :
Galonde, Nadine ; Université de Liège - ULiège > Chimie et bio-industries > Chimie générale et organique
Nott, Katherine ; Université de Liège - ULiège > Chimie et bio-industries > Chimie biologique industrielle
Richard, Gaetan ; Université de Liège - ULiège > Chimie et bio-industries > Chimie biologique industrielle
Debuigne, Antoine ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie des macromolécules et des matériaux organiques
Nicks, Francois ; Université de Liège - ULiège > Chimie et bio-industries > Chimie biologique industrielle
Jérôme, Christine ; Université de Liège - ULiège > Département de chimie (sciences) > Centre d'études et de rech. sur les macromolécules (CERM)
Fauconnier, Marie-Laure ; Université de Liège - ULiège > Chimie et bio-industries > Chimie générale et organique
Language :
English
Title :
Study of the Influence of Pure Ionic Liquids on the Lipase-catalyzed (Trans)esterification of Mannose Based on their Anion and Cation Nature
Publication date :
April 2013
Journal title :
Current Organic Chemistry
ISSN :
1385-2728
Publisher :
Bentham Science Publishers Ltd., Sharjah, United Arab Emirates
Coulon, D.; Girardin, M.; Engasser, JM.; Ghoul, M. Investigation of keys parameters of fructose oleate enzymatic synthesis catalyzed by an immobilized lipase. Industrial Crops and Products, 1997, 6(3-4), 375-381.
Kennedy, J.F.; Kumar, H.; Panesar, P.S.; Marwaha, S.S.; Goyal, R.; Parmar, A.; Kaur, S. Enzyme-catalyzed regioselective synthesis of sugar esters and related compounds. Journal of Chemical Technology & Biotechnology, 2006, 81(6), 866-876.
Shi, Y-G.; Li, J-R.; Chu, Y-H. Enzyme-catalyzed regioselective synthesis of sucrose-based esters. Journal of Chemical Technology & Biotechnology, 2011, 86(12), 1457-1468.
Chen, S-T.; Sookkheo, B.; Phutrahul, S.; Wang, K-T. Enzymes in Nonaqueous Solvents Applications in Carbohydrate and Peptide Preparation. Methods in Biotechnology, 2001, 15, 373-400.
Degn, P.; Zimmermann, W. Optimization of carbohydrate fatty acid ester synthesis in organic media by a lipase from Candida antarctica. Biotechnology and Bioengineering, 2001, 74(6), 483-491.
Flores, M.V.; Halling, P.J. Full model for reversible kinetics of lipasecatalyzed sugar-ester synthesis in 2-methyl-2-butanol. Biotechnology and Bioengineering, 2002, 78(7), 795-801.
Sheldon, R.A.; Lau, R.M.; Sorgedrager, M.J.; van Rantwijk, F.; Seddon, K.R. Biocatalysis in ionic liquids. Green Chemistry, 2002, 4(2), 147-151.
Liu, Q.B.; Janssen, M.H.A.; van Rantwijk, F.; Sheldon, R.A. Roomtemperature ionic liquids that dissolve carbohydrates in high concentrations. Green Chemistry, 2005, 7(1), 39-42.
Galonde, N.; Nott, K.; Debuigne, A.; Deleu, M.; Jerôme, C.; Paquot, M.; Wathelet, J-P. Use of ionic liquids for biocatalytic synthesis of sugar derivatives. Journal of Chemical Technology & Biotechnology, 2012, 87(4), 451-471.
Park, S.; Kazlauskas, R.J. Improved Preparation and Use of Room- Temperature Ionic Liquids in Lipase-Catalyzed Enantio- and Regioselective Acylations. The Journal of Organic Chemistry, 2001, 66(25), 8395-8401.
Kim, M.J.; Choi, M.Y.; Lee, J.K.; Ahn, Y. Enzymatic selective acylation of glycosides in ionic liquids: significantly enhanced reactivity and regioselectivity. Journal of Molecular Catalysis B: Enzymatic, 2003, 26(3-6), 115-118.
Ganske, F.; Bornscheuer, U.T. Optimization of lipase-catalyzed glucose fatty acid ester synthesis in a two-phase system containing ionic liquids and t- BuOH. Journal of Molecular Catalysis B: Enzymatic, 2005, 36(1-6), 40-42.
Ha S.; Hiep, N.; Koo, Y-M. Enhanced production of fructose palmitate by lipase-catalyzed esterification in ionic liquids. Biotechnology and Bioprocess Engineering, 2010, 15(1), 126-130.
Lee, S.H.; Ha, S.H.; Hiep, N.M.; Chang, W-J.; Koo, Y-M. Lipase-catalyzed synthesis of glucose fatty acid ester using ionic liquids mixtures. Journal of Biotechnology, 2008, 133(4), 486-489.
Lee, SH.; Dang, D.T.; Ha, S.H.; Chang, W-J.; Koo, Y-M. Lipase-catalyzed synthesis of fatty acid sugar ester using extremely supersaturated sugar solution in ionic liquids. Biotechnology and Bioengineering, 2008, 99(1), 1-8.
Ha, S.; Hiep, N.; Lee, S.; Koo, Y-M. Optimization of lipase-catalyzed glucose ester synthesis in ionic liquids. Bioprocess and Biosystems Engineering, 2010, 33(1), 63-70.
Mutschler, J.; Rausis, T.; Bourgeois, J-M.; Bastian, C.; Zufferey, D.; Mohrenz, I.V.; Fischer, F. Ionic liquid-coated immobilized lipase for the synthesis of methylglucose fatty acid esters. Green Chemistry, 2009, 11(11), 1793-1800.
Galletti, P.; Moretti, F.; Samori, C.; Tagliavini, E. Enzymatic acylation of levoglucosan in acetonitrile and ionic liquids. Green Chemistry, 2007, 9(9), 987-991.
Nara, S.J.; Mohile, S.S.; Harjani, J.R.; Naik, P.U.; Salunkhe, M.M. Influence of ionic liquids on the rates and regioselectivity of lipase-mediated biotransformations on 3,4,6-tri-O-acetyl-D-glucal. Journal of Molecular Catalysis B: Enzymatic, 2004, 28(1), 39-43.
Chen, Z-G.; Zong, M-H.; Li, G-J. Lipase-catalyzed acylation of konjac glucomannan in ionic liquids. Journal of Chemical Technology & Biotechnology, 2006, 81(7), 1225-1231.
Nott, K.; Brognaux, A.; Richard, G.; Laurent, P.; Favrelle, A.; Jérôme, C.; Blecker, C.; Wathelet, J-P.; Paquot, M.; Deleu, M. (Trans)esterification of mannose catalyzed by lipase from Candida antarctica in an improved reaction medium using co-solvents and molecular sieve. Preparative Biochemistry and Biotechnology, 2012, 42(4), 348-363.
Favrelle, A.; Boyère, C.; Laurent, P.; Broze, G.; Blecker, C.; Paquot, M.; Jérôme, C.; Debuigne, A. Enzymatic synthesis and surface active properties of novel hemifluorinated mannose esters. Carbohydrate Research, 2011, 346(9), 1161-1164.
Prakash, J.; Beljaars, L.; Harapanahalli, AK.; Zeinstra-Smith, M.; de Jager-Krikken, A.; Hessing, M.; Steen, H.; Poelstra, K. Tumor-targeted intracellular delivery of anticancer drugs through the mannose-6- phosphate/insulin-like growth factor II receptor. International Journal of Cancer, 2010, 126(8), 1966-1981.
Lee, S.H.; Nguyen, H.M.; Koo, Y.M.; Ha, S.H. Ultrasound-enhanced lipase activity in the synthesis of sugar ester using ionic liquids. Process Biochemistry, 2008, 43(9), 1009-1012.
Lee, S.; Koo, Y-M.; Ha, S. Influence of ionic liquids under controlled water activity and low halide content on lipase activity. Korean Journal of Chemical Engineering, 2008, 25(6), 1456-1462.
Ha, S.; Lee, S.; Dang, D.; Kwon, M.; Chang, W-J.; Yu, Y.; Byun, I.; Koo, YM. Enhanced stability of Candida antarctica lipase B in ionic liquids. Korean Journal of Chemical Engineering, 2008, 25, 291-294.
Van Rantwijk, F.; Secundo, F.; Sheldon, R.A. Structure and activity of Candida antarctica lipase B in ionic liquids. Green Chemistry, 2006, 8, 282-286.
Murugesan, S.; Linhardt, R.J. Ionic Liquids in Carbohydrate Chemistry - Current Trends and Future Directions. Current Organic Synthesis, 2005, 2(4), 437-451.
Klahn, M.; Lim, G.S.; Seduraman, A.; Wu, P. On the different roles of anions and cations in the solvation of enzymes in ionic liquids. Physical Chemistry Chemical Physics, 2011, 13(4), 1649-1662.
van Rantwijk, F.; Sheldon, R.A. Biocatalysis in Ionic Liquids. Chemical Reviews, 2007, 107(6), 2757-2785.
Gorke, J.; Srienc, F.; Kazlauskas, R. Toward advanced ionic liquids. Polar, enzyme-friendly solvents for biocatalysis. Biotechnology and Bioprocess Engineering, 2010, 15(1), 40-53.
Schofer, S.H.; Kaftzik, N.; Wasserscheid, P.; Kragl, U. Enzyme catalysis in ionic liquids: lipase catalysed kinetic resolution of 1-phenylethanol with improved enantioselectivity. Chemical Communications, 2001, 5, 425-426.
Kaar, J.L.; Jesionowski, A.M.; Berberich, J.A.; Moulton, R.; Russell, A.J. Impact of Ionic Liquid Physical Properties on Lipase Activity and Stability. Journal of the American Chemical Society, 2003, 125(14), 4125-4131.
Dupont, J. On the solid, liquid and solution structural organization of imidazolium ionic liquids. Journal of the Brazilian Chemical Society, 2004, 15(3), 341-350.
Zhuo, K.; Chen, Y.; Chen, J.; Bai, G.; Wang, J. Interactions of 1-butyl-3- methylimidazolium carboxylate ionic liquids with glucose in water: a study of volumetric properties, viscosity, conductivity and NMR. Physical Chemistry Chemical Physics, 2011, 13(32), 14542-14549.
