Lipase‐catalyzed synthesis of fatty acid sugar ester using extremely supersaturated sugar solution in ionic liquids
- 14 June 2007
- journal article
- research article
- Published by Wiley in Biotechnology & Bioengineering
- Vol. 99 (1), 1-8
- https://doi.org/10.1002/bit.21534
Abstract
The low solubility of sugars has hampered the lipase-catalyzed synthesis of fatty acid sugar esters in organic solvents and ionic liquids (ILs), because several solvents that are able to effectively dissolve sugars are detrimental to enzymes. In this work, in order to prepare a high concentration of sugars in ILs, we have developed a new procedure that entails mixing an aqueous sugar solution into ILs followed by removal of the water from the solution. The glucose concentrations in the supersaturated [Emim][TfO] and [Bmim][TfO] were 19 and 10 times higher, respectively, than the solubilities (6.1 and 4.8 g/L) of glucose in the ILs at 25°C. Furthermore, the supersaturated glucose solutions in ILs were maintained over a long period of time without any significant loss of glucose. In ILs that were extremely supersaturated with glucose, lipase-catalyzed esterifications of glucose with vinyl laurate, and lauric acid were successfully carried out. The conversion increased from 8% to 96% at 1 day of reaction by using supersaturated solution in [Bmim][TfO] which had dissolved glucose concentration of 400% higher than its solubility, compared with the reaction using saturated glucose solution. By making the glucose concentration in ILs much higher than the solubility through our novel and simple method, the initial rate and conversion of the lipase-catalyzed reaction were significantly improved. Biotechnol. Bioeng. 2008;99: 1–8.Keywords
This publication has 23 references indexed in Scilit:
- Optimization of lipase-catalyzed glucose fatty acid ester synthesis in a two-phase system containing ionic liquids and t-BuOHJournal of Molecular Catalysis B: Enzymatic, 2005
- Lipase-Catalyzed Glucose Fatty Acid Ester Synthesis in Ionic LiquidsOrganic Letters, 2005
- Dissolution kinetics of crystalline α-glucose in 2-methyl 2-butanolBiochemical Engineering Journal, 2005
- Solubilities in the Ternary System Alkali Metal Halide–Glucose–WaterJournal of Solution Chemistry, 2004
- Enzyme catalysis in ionic liquidsCurrent Opinion in Biotechnology, 2002
- Characterizing Ionic Liquids On the Basis of Multiple Solvation InteractionsJournal of the American Chemical Society, 2002
- Lipase-Catalyzed Enantioselective Acylation in the Ionic Liquid Solvent System: Reaction of Enzyme Anchored to the SolventChemistry Letters, 2001
- Lipase-catalysed synthesis of glucose fatty acid esters in tert-butanolBiotechnology Letters, 1999
- DESIGNER SOLVENTSChemical & Engineering News, 1998
- Enzyme Catalysed Preparation of 6-O-AcylglucopyranosidesSynthesis, 1990