Lipase-Catalyzed Synthesis and Characterization of 6-O-(11-Dodecenoic)-Glucose Ester in Ionic Liquids
Affiliation(s)
State Key Laboratory for Conservation and Utilization of Subtropical Agro-Bioresources, Nanning, China. School of Chemistry and Chemical Engineering, Guangxi University, Nanning, China.
State Key Laboratory for Conservation and Utilization of Subtropical Agro-Bioresources, Nanning, China. School of Chemistry and Chemical Engineering, Guangxi University, Nanning, China.
ABSTRACT
Novozym-435 Lipase-catalyzed transesterification of glucose with 11-dodecenoic ethyl ester in ionic liquids was investigated. The effect of substrate ratio, lipase content, and temperature on the activity and stability of lipase was also studied. The highest yield of sugar ester was obtained in 1-buty-3-methyl imidazolium tetrafluoroborate [Bmim][BF4] under such conditions as the reaction temperature of 55℃, the enzyme concentration of 20 mg/mL, the mole ratio of glucose/11-dodecenoic ethyl ester of 1:2, the water content of the system of 2%, Lipase Novozym-435 can use repeatedly 7 times. The structure of production was characterized by FTIR, HPLC, MS and NMR. The results show that the production is 6-O-(11-dodecenoic)-glucose ester.
Novozym-435 Lipase-catalyzed transesterification of glucose with 11-dodecenoic ethyl ester in ionic liquids was investigated. The effect of substrate ratio, lipase content, and temperature on the activity and stability of lipase was also studied. The highest yield of sugar ester was obtained in 1-buty-3-methyl imidazolium tetrafluoroborate [Bmim][BF4] under such conditions as the reaction temperature of 55℃, the enzyme concentration of 20 mg/mL, the mole ratio of glucose/11-dodecenoic ethyl ester of 1:2, the water content of the system of 2%, Lipase Novozym-435 can use repeatedly 7 times. The structure of production was characterized by FTIR, HPLC, MS and NMR. The results show that the production is 6-O-(11-dodecenoic)-glucose ester.
KEYWORDS
Ionic Liquids(ILs); 6-O-(11-Dodecenoic)-Glucose Ester; Lipase; 11-Dodecenoic Ethyl Ester; Glucose
Ionic Liquids(ILs); 6-O-(11-Dodecenoic)-Glucose Ester; Lipase; 11-Dodecenoic Ethyl Ester; Glucose
Cite this paper
Yao, P. , Huang, G. , Yan, W. , Zhang, X. , Li, Q. and Wei, Y. (2012) Lipase-Catalyzed Synthesis and Characterization of 6-O-(11-Dodecenoic)-Glucose Ester in Ionic Liquids. Advances in Chemical Engineering and Science, 2, 204-211. doi: 10.4236/aces.2012.22025.
Yao, P. , Huang, G. , Yan, W. , Zhang, X. , Li, Q. and Wei, Y. (2012) Lipase-Catalyzed Synthesis and Characterization of 6-O-(11-Dodecenoic)-Glucose Ester in Ionic Liquids. Advances in Chemical Engineering and Science, 2, 204-211. doi: 10.4236/aces.2012.22025.
References
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[1] M. V. Flores, K. Naraghi, J. M. Engasser and P. J. Halling, “Influence of Glucose Solubility and Dissolution Rate on the Kinetics of Lipase Catalyzed Synthesis of Glucose Laurate in 2-Methyl 2-Butanol,” Biotechnology and Bioengineering, Vol. 78, No. 7, 2002, pp.814-820. doi:10.1002/bit.10263 [2] J. F. Kennedy, H. Kumar, P. S. Panesar, S. S. Marwaha, R. Goyal, A. Parmar and S. Kaur, “Enzyme-Catalyzed Regioselective Synthesis of Sugar Esters and Related Compounds,” Journal of Chemical Technology & Biotechnology, Vol. 81, No. 6, 2006, pp. 866-876. doi:10.1002/jctb.1473 [3] M. Therisodt and A. M. Klibanov, “Facile Enzymatic Preparation of Monoacylated Sugars in Pyridine,” American Chemical Society, Vol. 108. No. 18, 1986, pp. 5638-5640. [4] F. Ganske and U. T. Bornscheuerv, “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, Vol. 36, No. 1-6, 2005, pp. 40-42. doi:10.1016/j.molcatb.2005.08.004 [5] S. Riva, J. Chopineau, A. P. G. Kieboom and A. M. Klibanov, “Protease-Catalyzed Regioselective Esterification of Sugars and Related Compounds in Anhydrous Dimethylformamide,” Journal of the American Chemical Society, Vol. 110, No. 2, 1988, pp. 584-589. doi:10.1021/ja00210a045 [6] H. S. Soedjak and J. E. Spradlin, “Enzymatic Transesterification of Sugars in Anhydrous Pyridine,” Biocatalysis and Biotransformation, Vol. 11, No. 3, 1994, pp. 241-248. doi:10.3109/10242429408998144 [7] F. J. Plou, M. A. Cruces, M. Bernable, M. Martin-Loma, J. L. Parra and A. Ballesteros, “Enzymatic Synthesis of Partially Acylated Sucrosesa,” Annals of the New York Academy of Sciences, Vol. 750, 1995, pp. 332-337. doi:10.1111/j.1749-6632.1995.tb19976.x [8] J. O. Rich, B. A. Bedell and J. S. Dordick, “Controlling Enzyme-Catalyzed Regioselectivity in Sugar Ester Synthesis,” Biotechnology and Bioengineering, Vol. 45, No. 5, 1995, pp. 426-434. doi:10.1002/bit.260450507 [9] Z. Yang and W. B. Pan, “Ionic Liquids: Green Solvents for Nonaqueous Biocatalysis,” Enzyme and Microbial Technology, Vol. 37, No. 1, 2005, pp. 19-28. doi:10.1016/j.enzmictec.2005.02.014 [10] N. Kimizuka and T. Nakashima, “Spontaneous Self-Assembly of Glycolipid Bilayer Membranes in Sugar-Philic Ionic Liquids and Formation of Ionogels,” Langmuir, Vol. 17, No. 22, 2001, pp. 6759-6761. doi:10.1021/la015523e [11] R. P. Swatloski, S. K. Spear, J. D. Holbrey and R. D. Rogers, “Dissolution of Cellose with Ionic Liquids,” Journal of the American Chemical Society, Vol. 124, No. 18, 2002, pp. 4974-4975. doi:10.1021/ja025790m [12] D. R. MacFarlane, J. Golding, S. Forsyth, M. Forsyth and G. B. Deacon, “Low Viscosity Ionic Liquids Based on Organic Salts of the Dicyanamide Anion,” Chemical Communications, No. 16, 2001, pp. 1430-1431. doi:10.1039/b103064g [13] S. A. Forsyth, D. R. MacFarlane, R. J. Thomson and M. V. Itzstein, “Rapid, Clean, and Mild O-Acetylation of Alcohols and Carbohydrates in an Ionic Liquid,” Chemical Communications, No. 7, 2002, pp. 714-715. doi:10.1039/b200306f [14] S. A. Forsyth and D. R. MacFarlane, “1-Alkyl-3-Methylbenzotriazolium Salts: Ionic Solvents and Electrolytes,” Journal of Materials Chemistry, Vol. 13, No. 10, 2003, pp. 2451-2456. doi:10.1039/b307931g [15] G. J. Huang, T. Wang, P. J. Yao and Y. A. Wei. “Studies on Enzymatic Synthesis of 6-O-Lauroylsucrose in Ionic Liquids,” Journal of Guangxi University: Natural Science Edition, Vol. 35, No. 3, 2010, pp. 455-461. [16] Y. Z. H. Wang , Q. L. Li, W. Yue, P. J. Yao and Y. A. Wei, “6-O-(10-Undecylenoyl)-D-Glucose: Controlled Enzymatic Synthesis and Structure Elucidation by 1H and 13C NMR,” Advanced Materials Research, Vol. 396-398, 2012, pp. 1318-1324. doi:10.4028/www.scientific.net/AMR.396-398.1318