DOI QR코드

DOI QR Code

Enzyme-catalyzed reactions in ionic liquids (Review)

  • 구윤모 (인하대학교) ;
  • 이상목 (인하대학교) ;
  • 하성호 (인하대학교) ;
  • 문윤희 (인하대학교)
  • Ku, Yun-Mo ;
  • Lee, Sang-Mok ;
  • Ha, Sung-Ho ;
  • Moon, Yun-Hee
  • 발행 : 20060000

초록

liquids have been suggested as potential “green solvents” due to their unique properties such as non-volatility, nonflamability, and a wide temperature range for liquid phase. This review describes recent advances ofbiocatalyst reactions in ionic liquids. Enzyme-catalyzed reactions in ionic liquids-transesterification, synthesis, conver-folding/refolding and the toxicity of ionic liquids are also discussed.

키워드

참고문헌

  1. Armstrong, N., Lencastre, A. D. and Gouaux, E., 'A new protein folding screen: application to the ligand binding domains ofa glutamate and kainate receptor and to lysozyme and carbonic anhydrase;' Protein Sci., 8,1475(1999) https://doi.org/10.1110/ps.8.7.1475
  2. Baudequin, C, Baudoux, J., Levillain, J., Cahard, D., Gaumont, A. C. and Plaquevent, J. C, 'Ionic liquids and chirality: opportunities and challenges;' Tetrahedron: Asymmetry, 14, 3081 (2003) https://doi.org/10.1016/S0957-4166(03)00596-2
  3. Blanchard, L. A. and Brennecke, J. F., 'High-pressure phase behavior ofionic liquid/$CO_{2}$system;' J. Phys. Chem. B., 105(12),2437 (2001) https://doi.org/10.1021/jp003309d
  4. Belafi-Bako, K., Dormo, N., Ulbert, O. and Gubicza, L., 'Application of pervaporation for removal of water produced during enzymatic esterification in ionic liquids;' Desalination, 149,267 (2002) https://doi.org/10.1016/S0011-9164(02)00781-6
  5. Chiappe, C, Leandri, E., Lucchesi, S. and Pieraccini, D., 'Biocatalysis in ionic liquids: the stereoconvergent hydrolysis of trans-,$\beta$-methylstyrene oxide catalyzed by soluble epoxide hydrolase;' J Mol. Catal. B: Enzym., 27, 243 (2004) https://doi.org/10.1016/j.molcatb.2003.12.008
  6. Cull, S. G, Holbrey, J. D., Vargas-Mora, V., Seddon, K. R. and Lye, G J., 'Room-temperature ionic liquids as replacements for organic solvents in multiphase bioprocess operations;' Biotechnol. Bioeng., 69(2),227 (2000) https://doi.org/10.1002/(SICI)1097-0290(20000720)69:2<227::AID-BIT12>3.0.CO;2-0
  7. de Diego, T., Lozano, P., Vaultier, M. and Iborra, J. L., 'Understanding structure-stability relationships of Candida antarctica lipase B in ionic liquids;' Biomacromolecules, 6, 1457 (2005) https://doi.org/10.1021/bm049259q
  8. Eckstein, M., Sesing, M., Kragl, U. and Adlercreutz, P., 'At low water activity $\alpha$-chymotrypsin is more active in an ionic liquid than in nonionic organic solvents;' Biotechnol. Lett., 24, 867 (2002) https://doi.org/10.1023/A:1015564608261
  9. Eckstein, M., Wasserseheid, P. and Kragl, U., 'Enhanced enantioselectivity oflipase from Pseudomonas sp. at high temperatures and fixed water activity in the ionic liquid 1-butyl-3-methylimidazolium bis[(tritluoromethyl) sulfony1] amide;' Biotechnol. Lett., 24, 763 (2002) https://doi.org/10.1023/A:1015563801977
  10. Erbeldinger, M., Mesiano, A. J. and Russel, A. J., 'Enzymatic catalysis of formation of Z-aspartame in ionic liquid- an alternative to enzymatic catalysis in organic solvents;' Biotechnol. Prog., 16(6), 1129 (2000) https://doi.org/10.1021/bp000094g
  11. Gaisberger, R. P., Fechter, M. H. and Griengl, H., 'The first hydroxynitrile lyase catalyze cyanohydrin formation in ionic liquids;' Tetrahedron: Asymmetry, 15,2959 (2004) https://doi.org/10.1016/j.tetasy.2004.06.028
  12. Ganske, F. and Bomscheuer, U. T., 'Lipase-catalyzed glucose fatty acid ester synthesis in ionic liquids;' Org. Lett., 0(0), A-B (2005)
  13. Gordon, C. M., 'New developments in catalysis using ionic liquids;' Appl. Catal., 222,101 (2001) https://doi.org/10.1016/S0926-860X(01)00834-1
  14. Howardh, J., James, P. and Dai, J., 'Immobilized Baker's yeast reduction ofketones in an ionic liquid, [BMIM][$PF_{6}$] and water mix;' Tetrahedron Lett., 42, 7517 (2001) https://doi.org/10.1016/S0040-4039(01)01601-X
  15. Irimescu, R. and Kato, K., 'Investigation ofionic liquids as reaction media for enzymatic enantioselective acylation of amines;' J. Mol. Catal. B: Enzym., 30, 189 (2004) https://doi.org/10.1016/j.molcatb.2004.05.003
  16. Irimescu, R and Kato, K, 'Lipase-catalyzed enantioselective reaction ofamines with carboxylic acids under reduced pressure in non-solvent system and in ionic liquids;' Tetrahedron Lett., 45, 523 (2004) https://doi.org/10.1016/j.tetlet.2003.10.210
  17. Itoh, T., Akasaki, E, Kudo, K and Nishimura, Y., 'Efficient lipase-catalyzed enantioselective acylation under reduced pressure conditions in an ionic liquid solvent system;' Chem. Lett., 31(2),154 (2002) https://doi.org/10.1246/cl.2002.154
  18. Itoh, T., Akasaki, E, Kudo, K and Shirakami, S., 'Lipase-catalyzed enantioselective acylation in the ionic liquid solvent system: reaction of enzyme anchored to the solvent;' Chem. Lett., 30(3), 262 (2001) https://doi.org/10.1246/cl.2001.262
  19. Itoh, T., Nishimura, Y., Kashiwagi, M., Onaka, M., In Rogers, R. D. and Seddon, K R, Ionic Liquids as Green Solvents: Progress and Prospects, ACS Symposium Series, American Chemical Society, Oxford University Press, Oxford, Chapter 21 (2003)
  20. Itoh, T., Nishimura, Y., Ouchi, N. and Hayase, S., '1-Buty1-2,3 dimethylimidazolium tetrafluoroborate: the most desirable ionic liquid solvent for recycling use ofenzyme in lipase-catalyzed transesterification using vinyl acetate as acyl donor,' J. Mol. Catal. B: Enzym., 26, 41 (2003) https://doi.org/10.1016/S1381-1177(03)00147-4
  21. Jain, N., Kumar, A., Chauhan, S. and Chauhan, S. M. S., 'Chemical and biochemical transformations in ionic liquids;' Tetrahedron, 61(5), 1015 (2004)
  22. Jastorff, B., Stamnann, R., Ranke, l, Molter, K., Stock, F, Oberheitmann, B., Hoffinann, W, Hoffinann, l, Nilchter, M., Ondruschka, B. and Filser, J., 'How hazardous are ionic liquids- Structure-activity relationships and biological testing as important elements for sustainability evaluation;' Green Chem., 5, 136 (2003) https://doi.org/10.1039/b211971d
  23. Kaar, J L., Jesionowski, A M., Berberich, J. A, Moilto, R. and Russell, A. L., 'Impact ofionic liquid physical properties on lipase activity and stability;' J. Am. Chem. Soc., 125(14),4125 (2003) https://doi.org/10.1021/ja028557x
  24. Kaftzik, N., Kroutil, W., Faber, K. and Kragl, U., 'Mandelate racemase activity in ionic liquids: scopes and limitations;' J. Mol. Catal. A: Chem., 214, 107 (2004) https://doi.org/10.1016/j.molcata.2003.11.034
  25. Kaftzik, N., Wasserscheid, P and Kragl, U., 'Use ofionic liquids to increase the yield and enzyme stability in the ,$\beta$-galactosidase catalyzed synthesis ofN-acetyllactosamine;' Organ. Proc. Res. Dev., 6(4), 553 (2002)
  26. Kielbasinski, P, Albrycht, M., Luczak, l and Mikolajczyk, M., 'Enzymatic reactions in ionic liquids: lipase-catalyzed kinetic resolution ofracemic, P-chiral hydroxymethanephosphinates and hydroxymethylphosphine oxides;' Tetrahedron: Asymmetry, 13, 735 (2002) https://doi.org/10.1016/S0957-4166(02)00167-2
  27. Kim, K. W., Song, B., Choi, M. Y. and Kim, M. J., 'Biocatalysis in ionic liquids: markedly enhanced enantioselectivity of lipase;' Org. Lett., 3( 10), 1507 (2001) https://doi.org/10.1021/ol015824f
  28. Kim, M. J., Choi, M. Y., Lee, J. K. and Ahn, Y. J., 'Enzymatic selective acylation ofglycosides in ionic liquids: significantly enhanced reactivity and regioselectivity;' J. Mol. Catal. B: Enzyrn., 26, 115 (2003) https://doi.org/10.1016/j.molcatb.2003.04.001
  29. Kragl, U., Eckstein, M. and Kaftzik, N., 'Enzyme catalysis in ionic liquids;' Curr. Opin. Biotechnol., 13, 565 (2002) https://doi.org/10.1016/S0958-1669(02)00353-1
  30. Kragl, U., Kaftzik, N., Schofer, S. H., Eckstein, M., Wasserscheid, P and Hilgers, C., 'Enzyme catalysis in the presence of ionic liquids;' Chem. Today, 19,22 (2001)
  31. Laszlo, J. A. and Compton, D. L., '$\alpha$-Chymotrypsin catalysis in imidazolium- based ionic liquids;' Biotechnol. Bioeng., 75(2),181 (2001) https://doi.org/10.1002/bit.1177
  32. Laszlo, J. A. and Compton, D. L., 'Comparison ofperoxidase activities ofhemin, cytochrome C and microperoxidase-ll in molecular solvents and imidazolium- based ionic liquids;' J. Mol. Catal. B: Enzym., 18, 109 (2002) https://doi.org/10.1016/S1381-1177(02)00074-7
  33. Lau, R. M., Rantwijk, F. V., Seddon, K. R. and Sheldon, R. A., 'Lipasecatalyzed reactions in ionic liquids;' Org. Lett., 2(26), 4189 (2000) https://doi.org/10.1021/ol006732d
  34. Lee, S.-M., Chang, W.-J., Choi, A.-R. and Koo, Y.-M., 'Influence of ionic liquids on the growth of Escherichin colt:' Korean J. Chem. Eng., 22, 687 (2005) https://doi.org/10.1007/BF02705783
  35. Lozano, P., de Diego, T., Carrie, D., Vaultier, M. and Ibarra, J. L., 'Enzymatic ester synthesis in ionic liquids;' J. Mol. Catal. B: Enzym., 21,9(2003) https://doi.org/10.1016/S1381-1177(02)00128-5
  36. Lozano, P, de Diego, T., Carrie, D., Vaultier, M. and lborra, J. L., 'Overstabilization of Candida antarctica lipase B by ionic liquids in ester synthesis;' Biotechnol. Lett., 23, 1529 (2001) https://doi.org/10.1023/A:1011697609756
  37. Lozano, P., de Diego, T., Carrie, D., Vaultier, M. and Ibarra, J. L., 'Synthesis ofglycidyl esters catalyzed by lipases in ionic liquids and supercritical carbon dioxide;' J. Mol. Catal. A: Chern., 214, 113 (2004) https://doi.org/10.1016/j.molcata.2003.09.034
  38. Lozano, P, de Diego, T., Guegan, J. P, Vaultier, M. and Ibarra, J. L., 'Stabilization of a-ehymotrypsin by ionic liquids in transesterification reactions;' Biotechnol. Bioeng., 75(5), 563 (2001) https://doi.org/10.1002/bit.10089
  39. Marsh, K. N., Boxall, J. A. and Lichtenthaler, R, 'Room temperature ionic liquids and their mixtures- a revieW,' Fluid Phase Equilib., 219, 93 (2004) https://doi.org/10.1016/j.fluid.2004.02.003
  40. Marsh, K N., Deev, A, Wu, A C-T., Tran, E and Klamt, A, 'Room temperature ionic liquids as replacements for conventional solvents - a review;' Korean J. Chem. Eng., 19, 357 (2002) https://doi.org/10.1007/BF02697140
  41. Maruyama, T., Yamamura, H., Kotani, T., Kamiya, N. and Goto, M., 'Poly(ethylene glycol)-lipase complexes that are highly active and enantioselective in ionic liquids;' Org. Biomol. Chem., 2(8), 1239 (2004) https://doi.org/10.1039/b401012d
  42. Matsumoto, M., Mochiduki, K, Fukunishi, K. and Kondo, K, 'Extraction oforganic acids using imidazolium-based ionic liquids and their toxicity to Lactobacillus rhamnosus;' Sep. Purif Technol., 40, 97 (2004) https://doi.org/10.1016/j.seppur.2004.01.009
  43. Mohile, S. S., Potdar, M. K., HaJjani, J. R., Nara, S. J. and Salunkhe, M. M., 'Ionic liquids: efficient additives for Candida rugosa lipasecatalyzed enantioselective hydrolysis ofbuty1 2-(4-chlorophenoxy) propionate;' J. Mol. Catal. B: Enzym., 30, 185 (2004) https://doi.org/10.1016/j.molcatb.2004.05.002
  44. Nara, S. J., HaJjani, J. R. and Salunkhe, M. M., 'Lipase-catalyzed transesterification in ionic liquids and organic solvents: a comprehensive studY,' Tetrahedron Lett., 43, 2979 (2002) https://doi.org/10.1016/S0040-4039(02)00420-3
  45. Nara, S. J., HaJjani, J. R., Salunkhe, M. M., Mane, A. T. and Wadgaonkar, P. P., 'Lipase-catalyzed polyester synthesis in 1-buty1-3methylimidazolium hexafluorophosphate ionic liquid;' Tetrahedron Lett., 44, 1371 (2003) https://doi.org/10.1016/S0040-4039(02)02889-7
  46. Nara, S. J., Mohile, S. S., Hmjani, J. R., Jitendra R., Naik, P. U. and Salunkhe, M. M., 'Influence of ionic liquids on the rates and regi. oselectivity of lipase-mediated biotransformations on 3,4,6-tri-O acety1-D-glucal;' J. Mol. Catal. B: Enzym., 28, 39 (2004) https://doi.org/10.1016/j.molcatb.2004.01.010
  47. Okrasa, K, Guibe-Jampel, E. and Therisod, M., 'Ionic liquids as a new reaction medium for oxidase-peroxidase-catalyzed sulfoxidation;' Tetrahedron Asymmetry, 14,2487 (2003) https://doi.org/10.1016/S0957-4166(03)00578-0
  48. Olivier-Bourbigou, H. and Magna, L., 'Ionic liquids: perspectives for organic and catalytic reactions;' J. Mol. Catal. A: Chem., 182-183. 419(2002) https://doi.org/10.1016/S1381-1169(01)00465-4
  49. Panke, S. and Wubbolts, M. G, 'Enzyme technology and bioprocess engineering;' Curro Opin. Biotechnol., 13, 111 (2002) https://doi.org/10.1016/S0958-1669(02)00302-6
  50. Park, S. S. and Kazlauskas, R. J., 'Biocatalysis in ionic liquids-advantages beyond green technology,' Curr. Opin. Biotechnol., 14, 432 (2003) https://doi.org/10.1016/S0958-1669(03)00100-9
  51. Park, S. S. and Kazlauskas, R. J., 'Improved preparation and use ofroom temperature ionic liquids in lipase-catalyzed enantio- and regioselective acylations;' J. Org. Chem., 66(25), 8395 (2001) https://doi.org/10.1021/jo015761e
  52. Persson, M. and Bomscheuer, U. T., 'Increased stability of an esterase from Bacillus Stearothermophilus in ionic liquids as compared to organic solvents;' J. Mol. Catal. B: Enzym., 22, 21 (2003) https://doi.org/10.1016/S1381-1177(02)00294-1
  53. Poole, C. F., 'Chromatographic and spectroscopic methods for the determination of solvent properties ofroom temperature ionic liquids;' J. of Chromatogr. A, 1037,49 (2004) https://doi.org/10.1016/j.chroma.2003.10.127
  54. Ranke, J., Molter, K., Stock, F., Bottin-Weber, U., Poczobutt, J., Hoffmann, J., Ondruschka, B., Filser, J. and Jastorff, B., 'Biological effects of imidazolium ionic liquids with varying chain lengths in acute Vibrio fischeri and WST-1 cell viability assays;' Ecotoxicol. Environ. Saf, 58, 396 (2004) https://doi.org/10.1016/S0147-6513(03)00105-2
  55. Rantwijk, F. V., Lau, R. M. and Sheldon, R. A., 'Biocatalytic transformations in ionic liquids;' Trends Biotechnol., 21(3), 131 (2003) https://doi.org/10.1016/S0167-7799(03)00008-8
  56. Rasalkar, M. S., Potdar, M. K. and Salunkhe, M. M., 'Pseudomonas cepacia lipase-catalyzed resolution ofracemic alcohols in ionic liquid using succinic anhydride: role oftriethylamine in enhancement of catalytic activity,' J. Mol. Catal. B: Enzym., 27, 267 (2004) https://doi.org/10.1016/j.molcatb.2003.12.009
  57. Schfer, S. H., Kaftzik, N., Wasserscheid, P. and Kragl, U., 'Enzyme catalysis in ionic liquids: lipase-catalyzed kinetic resolution of I-phenylethanol with improved enantioselectivity,' Chem. Commun., 425 (2001)
  58. Schofer, T., Rodrigues, C. M., Afonso, C. A. M. and Crespo, J. G., 'Selective recovery of solutes from ionic liquids by pervaporation-a novel approach for purification and green processing' Chem. Commun., 1,1622 (2001)
  59. Summers, C. A. and Flowers, R. A., 'Protein renaturation by the liquid organic salt ethylammonium nitrate;' Protein Sci., 9, 2001 (2000) https://doi.org/10.1110/ps.9.10.2001
  60. Swatloski, R. P., Holbrey, J. D. and Rogers, R. D, 'Using Caenorhabditis elegans to probe toxicity of 1-alky1-3-methylimidazolium chloride based ionic liquids;' Chem. Commun., 6, 668 (2004)
  61. Swatloski, R. P., Spear, S. K., Holbrey, J. D. and Rogers, R. D, 'Dissolution of cellulose with ionic liquids;' J. Am. Chem. Soc., 124,4974 (2002) https://doi.org/10.1021/ja025790m
  62. UIbert, O., Frater, T., Belafi-Bako, K. and Gubicza, L., 'Enhanced enantioselectivity of Candida rugosa lipase in ionic liquids as compared to organic solvents;' J. Mol. Catal. B: Enzym., 31, 39 (2004) https://doi.org/10.1016/j.molcatb.2004.07.003
  63. Uyama, H., Takamoto, T. and Kobayashi, S., 'Enzymatic synthesis of polyesters in ionic liquids;' Polym. J., 34, 94 (2002) https://doi.org/10.1295/polymj.34.94
  64. Welton, T., 'Ionic liquids in catalysis;' Chem. Rev., 248, 2459 (2004)
  65. Wilkes, J. S., 'Properties of ionic liquid solvents for catalysis;' J. Mol. Catal. A: Chem., 214, 11 (2004) https://doi.org/10.1016/j.molcata.2003.11.029
  66. Yang, Z. and Pan, W, 'Ionic liquids: green solvents for nonaqueous biocatalysis;' Enzyme and Microbial Technology, 37, 19 (2005) https://doi.org/10.1016/j.enzmictec.2005.02.014
  67. Zhao, D., Wu, M., Kou, Y. and Min, E., 'Ionic liquids: applications in catalysis;' Catal. Today, 74, 157 (2002) https://doi.org/10.1016/S0920-5861(01)00541-7
  68. Zhao, H. and Malhotra, S. V., 'Enzymatic resolution of amino acid esters using ionic liquid N-ethylpyridinium trifluoroacetate;' Biotechnol. Lett., 24, 1257 (2002) https://doi.org/10.1023/A:1016205924504
  69. Zhao, H., Luo, R. G. and Malhotra, S. V., 'Kinetic study on the enzymatic resolution of homophenylalanine ester using ionic liquids;' Biotechnol. Progress, 19(3), 1016 (2003) https://doi.org/10.1021/bp025721b
  70. Zhao, Y. J., Xin, J. Y., Li Z., Xia, C. G. and Li, S.B., 'The lipase-catalyzed stereoselective hydrolysis ofthe racemic naproxen methyl ester in an aqueous organic biphasic system and an aqueous ionic liquid biphasic system;' Fenzi Cuihua, 18(1), (2004)