Effect of water activity on the lipase catalyzed esterification of geraniol in ionic liquid [bmim]PF6

Biotechnology and Bioengineering

Volumn 93, Issue 2, 2006, Pages 318-324

  Barahona, Donifan ^a   Pfromm, Peter H ^a   Rezac, Mary E ^a  

^a Sunflower Networking Group   (United States)

Author keywords

bmim PF6; Esterification; Ionic liquids; Lipase; Water

Indexed keywords

BYPRODUCTS; ENZYME KINETICS; ESTERIFICATION; IONIC CONDUCTION; ORGANIC SOLVENTS; RATE CONSTANTS;

[BMIM]PF6; IONIC LIQUIDS; LIPASE; WATER ACTIVITY;

WATER;

GERANIOL; SOLVENT; TRIACYLGLYCEROL LIPASE; VOLATILE ORGANIC COMPOUND; WATER;

AQUEOUS SOLUTION; ARTICLE; CANDIDA ANTARCTICA; CATALYSIS; ENZYME ACTIVATION; ENZYME MECHANISM; ENZYME STABILITY; ENZYME SUBSTRATE; EQUILIBRIUM CONSTANT; ESTERIFICATION; REACTION ANALYSIS; THERMODYNAMICS; VAPOR PRESSURE;

CATALYSIS; ESTERIFICATION; IMIDAZOLES; LIPASE; TERPENES; WATER;

CANDIDA ANTARCTICA;

EID: 33645638804     PISSN: 00063592     EISSN: 10970290     Source Type: Journal    
DOI: 10.1002/bit.20723     Document Type: Article

References (38)

1. Adam D. 2000. Clean and green. . .but are they mean? Nature 407:938-940.
2. Akoh CC, Claon PA. 1994. Enzymatic synthesis of geranyl acetate in n-hexane with Candida antarctica lipases. J Am Chem Soc 71(6):575-578.
3. Anthony JL, Maginn EJ, Brennecke JF. 2001. Solution thermodynamics of imidazolium-based ionic liquids and water. J Phys Chem B 105:10942-10949.
4. Bailey JE, Ollis DF. 1986. Biochemical engineering fundamentals. Washington DC: McGraw Hill.
5. Barahona D. 2005. Enzymatic reactions in ionic liquids. MS thesis, Kansas State University. 123 p.
6. Bartling K, Thompson JU, Pfromm PH, Czermak P, Rezac ME. 2001. Lipase-catalyzed synthesis of geranyl acetate in n-hexane with membrane-mediated water removal. Biotechnol Bioeng 75(6):676-681.
7. Berberich JA, Kaar JL, Russell AJ. 2003. Use of salt hydrate pairs to control water activity for enzyme catalysis in ionic liquids. Biotechnol Prog 19(3):1029-1032.
8. Chulalaknanukul W, Condoret J, Combes D. 1992. Kinetics of geranyl acetate synthesis by lipase-catalyzed transesterification in n-hexane. Enzyme Microb Technol 14:293-298.
9. Elderbinger M, Mesiano AJ, Russell AJ. 2000. Enzymatic catalysis of formation of Z-aspartame in ionic liquids-An alternative to enzymatic catalysis in organic solvents. Biotechnol Prog 16:1129-1131.
10. FDA. 2004. Title 21 (6). Subchapter E, subpart B: Animal drugs, feeds, and related products.
11. Gandhi NN, Patil NS, Sawant SB, Joshi JB. 2000. Lipase-catalyzed esterification. Catal Rev-Sci Eng 42(4):439-480.
12. Grob S, Hasse H. 2005. Thermodynamics of phase and chemical equilibrium in a strongly nonideal esterification system. J Chem Eng Data 50(1):92-101.
13. Gubicza L, Nemestothy N, Prater T, Belafi-Bako K. 2003. Enzymatic esterification in ionic liquids integrated with pervaporation for water removal. Green Chem 3:236-239.
14. Halling PJ. 1990. Solvent selection for biocatalysis in mainly organic systems: Predictions of effects on equilibrium position. Biotechnol Bioeng 35:691-701.
15. Halling PJ. 1994. Thermodynamic predictions for biocatalysis in nonconventional media: Theory, tests, and recommendations for experimental design and analysis. Enzyme Microb Technol 16:178-206.
16. Huang S, Chang H. 1999. Kinetic study on the esterification of geraniol and acetic acid in organic solvents using surfactant-coated lipase. J Chem Technol Biotechnol 74:183-187.
17. Huddleston JG, Visser AE, Reichert E, Willauer HD, Broker GA, Rogers RD. 2001. Characterization and comparison of hydrophilic and hydrophobic room temperature ionic liquids incorporating the imidazolium cation. Green Chem 3:156-164.
18. Husum TL, Christel JT, Chirstensen MW, Kirk O. 2001. Enzyme catalyzed synthesis in ambient temperature ionic liquids. Biocatal Biotransform 19:331-338.
19. Itoh T, Akasaki E, Kudo K, Shirakami S. 2001. Lipase-catalyzed enantioselective acylation in the ionic liquids solvent system: Reaction of enzyme anchored to the solvent. Chem Lett 30(3):262-263.
20. Kaar JL, Jesionowski AM, Berberich JA, Moulton R, Russell AJ. 2003. Impact of ionic liquid physical properties on lipase activity and stability. J Am Chem Soc 125:4125-4131.
21. Kaftzik N, Wasserscheid P, Kragl U. 2002. Use of ionic liquids to increase the yield and enzyme stability in the β-galactosidase catalized synthesis of N-acetyllactosamine. Org Process Res Dev 6:553-557.
22. Kang I, Rezac ME, Pfromm PH. 2004. Membrane permeation based sensing for dissolved water in organic micro-aqueous media. J Mem Sci 239(2):213-217.
23. Kang I, Pfromm PH, Rezac ME. 2005. Real time measurement and control of thermodynamic water activities for enzymatic catalysis in hexane. J Biotechnol: Published online.
24. Klibanov AM. 2001. Improving enzymes by using them in organic solvents. Nature 409:241-246.
25. Krishna SH. 2002. Developments and trends in enzyme catalysis in nonconventional media. Biotechol Adv 20:239-267.
26. Lozano P, De Diego T, Carrie D, Vaultier M, Iborra JL. 2001. Overstabilization of Candida antarctica lipase B by ionic liquids in ester synthesis. Biotechnol Lett 23:1529-1533.
27. Model M, Tester JW. 1997. Thermodynamics and its applications. Cambridge, MA, USA: Prentice Hall.
28. Nara SJ, Harjani JR, Salunkhe M. 2002. Lipase catalyzed transesterification in ionic liquids and organic solvents: A comparative study. Tetrahedron Lett 43:2979-2982.
29. Novozyme, Inc. 2003. Technical data sheet 2003-03782-01.
30. Peres C, Gomes Da Silva MD, Barreiros S. 2003. Water activity effects on geranyl acetate synthesis catalyzed by Novozym in supercritical ethane and in supercritical carbon dioxide. J Agric Food Chem 51:1884-1888.
31. Seddon KR, Earle MJ. 2002. Ionic liquids: Green solvents for the future. In: Rogers RD, Seddon KR, editors. Ionic liquids: Industrial applications for green chemistry. ACS symposium series 818. Washington, D.C.: American Chemical Society.
32. Seddon KR, Stark A, Torres M. 2000. Influence of chloride, water and organic solvents on the physical properties of ionic liquids. Pure Appl Chem 72(12):2275-2287.
33. Seddon KR, Stark A, Torres M. 2002. Viscosity and density of 1-alkyl-3-methylimidazolium ionic liquids. In: Seddon KR, Rogers RD, editors. Ionic liquids: Industrial applications for green chemistry. ACS symposyum series 818. Washington D.C., USA: American Chemical Society.
34. Sheldon RA, Lau RM, Sorgedrager MJ, Rantwijk F, Seddon KR. 2002. Biocatalysis in ionic liquids. Green Chem 4:147-151.
35. Swatloski RP, Visser AE, Reichert MW, Broker GA, Farina LM, Holbrey JD, Rogers RD. 2001. Solvation of 1-butyl-3-methylimidazolium hexafluorophosphate in aqueous ethanol-A green solution for dissolving hydrophobic ionic liquids. Chem Commun 20:2070-2071.
36. Valivety RH, Johnston GA, Suckling CJ, Halling PJ. 1991. Solvent effects on biocatalysis in organic systems: Equilibrium position and rates of lipase catalyzed esterification. Biotechnol Bioeng 38:1137-1143.
37. Valivety RH, Halling PJ, Macrae AR. 1992. Reaction rate with suspended lipase catalyst shows similar dependence on water activity in different organic solvents. Biochim Biophys Acta 1118:218-222.
38. Wong DS, Chen JP, Chang JM, Chou CH. 2002. Phase equilibria of water and ionic liquids [emim]PF6 and [bmim]PF6. Fluid Phase Equilib 194-197:1089-1095.