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RETRACTED ARTICLE: Enzyme performance in ionic liquids

  • Invited Review Paper
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This article was retracted on 01 January 2013

Abstract

Ionic liquids (ILs) having unique properties such as no measurable vapor pressure, nonflammability and a wide temperature range of liquid phase have been recognized as potential green solvents. As a result, ILs have been extensively explored as reaction media for various biocatalytic reactions over a decade. Enzyme activities in ILs are generally comparable with or higher than those observed in conventional organic solvents. Furthermore, enhanced thermal and operational stabilities and regio- or enantioselectivities have been observed in many cases. Thus, ILs offer new possibilities for the application of solvent engineering to biocatalytic reactions. This review discusses the effect of physicochemical properties of ILs on biocatalysis with respect to enzyme activity, stability and selectivity by systematizing literature data on enzyme-catalyzed reaction in ILs.

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References

  1. T. Welton, Chem. Rev., 99, 2071 (1999).

    Article  CAS  Google Scholar 

  2. M. Deetlefs and K. R. Seddon, Chim. Oggi, 24, 16 (2006).

    CAS  Google Scholar 

  3. M. J. Earle, J. M. S. S. Esperancüa, M. A. Gilea, J. N. Canongia Lopes, L. P. N. Rebelo, J.W. Magee, K. R. Seddon and J. A. Widegren, Nature, 439, 831 (2006).

    Article  CAS  Google Scholar 

  4. M. Kosmulski, J. Gustafsson and J. B. Rosenholm, Thermochim. Acta, 412, 47 (2004).

    Article  CAS  Google Scholar 

  5. P. Wasserscheid and T. Welton, Eds., Ionic liquids in synthesis, Wiley-VCH, Weinheim (2003).

    Google Scholar 

  6. A. M. Klibanov, Nature, 409, 241 (2001).

    Article  CAS  Google Scholar 

  7. M. N. Gupta, Eur. J. Biochem., 203, 25 (1992).

    Article  CAS  Google Scholar 

  8. M. N. Gupta and I. Roy, Eur. J. Biochem., 271, 2575 (2004).

    Article  CAS  Google Scholar 

  9. A.V. Levashov and N. L. Klyachko, Izv. Akad. Nauk, Ser.: Khim., 1638 (2001).

  10. K. Martinek, A.V. Levashov, N.L. Klyachko and I.V. Berezin, Dokl. Akad. Nauk SSSR, 236, 920 (1977).

    CAS  Google Scholar 

  11. S.G. Cull, J. D. Holbrey, V. Vargas-Mora, K. R. Seddon and G. J. Lye, Biotechnol. Bioeng., 69, 227 (2000).

    Article  CAS  Google Scholar 

  12. D. K. Magnuson, J.W. Bodley and D. F. Evans, J. Solution Chem., 13, 583 (1984).

    Article  CAS  Google Scholar 

  13. Y.-H. Moon, S.M. Lee, S. H. Ha and Y.-M. Koo, Korean J. Chem. Eng., 23, 247 (2006).

    Article  CAS  Google Scholar 

  14. U. Kragl, M. Eckstein and N. Kaftzik, Curr. Opin. Biotechnol., 13, 565 (2002).

    Article  CAS  Google Scholar 

  15. S. Park and R. J. Kazlauskas, Curr. Opin. Biotechnol., 14, 432 (2003).

    Article  CAS  Google Scholar 

  16. Z. Yang and W. Pan, Enzyme Microb. Technol., 37, 19 (2005).

    Article  CAS  Google Scholar 

  17. F. van Rantwijk and R. A. Sheldon, Chem. Rev., 107, 2757 (2007).

    Article  Google Scholar 

  18. S. H. Schofer, N. Kaftzik, P. Wasserscheid and U. Kragl, Chem. Commun., 425 (2001).

  19. P. Lozano, T. De Diego, J. P. Guegan, M. Vaultier and J. L. Iborra, Biotechnol. Bioeng., 75, 563 (2001).

    Article  CAS  Google Scholar 

  20. T. Maruyama, H. Yamamura, T. Kotani, N. Kamiya and M. Goto, Org. Biomol. Chem., 2, 1239 (2004).

    Article  CAS  Google Scholar 

  21. K. Nakashima, T. Maruyama, N. Kamiya and M. Goto, Chem. Commun., 4297 (2005).

  22. K. Martinek, A.M. Klibanov, G. P. Samokhin, A. N. Semenov and I. V. Berezin, Bioorg. Khim., 3, 696 (1977).

    CAS  Google Scholar 

  23. S.V. Muginova, A. Z. Galimova, A. E. Polyakov and T.N. Shekhovtsova, J. Anal. Chem., 65, 331 (2010).

    Article  CAS  Google Scholar 

  24. A. K. Gladilin and A. V. Levashov, Biokhimiya, 63, 408 (1998).

    Google Scholar 

  25. M. E. Diaz-Garcia and M. J. Valencia-Gonzalez, Talanta, 42, 1763 (1995).

    Article  CAS  Google Scholar 

  26. A.V. Levashov and N. L. Klyachko, Izv. Akad. Nauk, Ser.: Khim., 1638 (2001).

  27. A. Zaks and A.M. Klibanov, Proc. Natl. Acad. Sci. U.S.A., 82, 3192 (1985).

    Article  CAS  Google Scholar 

  28. A. M. Klibanov, Chemtech., 16, 354 (1986).

    CAS  Google Scholar 

  29. S. Park and R. J. Kazlauskas, J. Org. Chem., 66, 8395 (2001).

    Article  CAS  Google Scholar 

  30. P. Wasserscheid and T. Welton, Eds., Ionic liquids in synthesis, Wiley-VCH, Weinheim (2003).

    Google Scholar 

  31. H. Ohno, Ed., Electrochemical aspects of ionic liquids, Hoboken, Wiley (2005).

    Google Scholar 

  32. H. Olivier-Bourbigou and L. Magna, J. Mol. Catal. A: Chem., 182–183, 419 (2002).

    Article  Google Scholar 

  33. J. L. Anderson, J. Ding, T. Welton and D.W. Armstrong, J. Am. Chem. Soc., 124, 14247 (2002).

    Article  CAS  Google Scholar 

  34. T. L. Greaves and C. J. Drummond, Chem. Rev., 108, 206 (2008).

    Article  CAS  Google Scholar 

  35. N. Kimizuka and T. Nakashima, Langmuir, 17, 6759 (2001).

    Article  CAS  Google Scholar 

  36. R. P. Swatloski, S. K. Spear, J. D. Holbrey and R. D. Rogers, J. Am. Chem. Soc., 124, 4974 (2002).

    Article  CAS  Google Scholar 

  37. Y. Fukaya, K. Hayashi, M. Wada and H. Ohno, Green Chem., 10, 44 (2008).

    Article  CAS  Google Scholar 

  38. M. Eckstein, M. Sesing, U. Kragl and P. Adlercreutz, Biotechnol. Lett., 24, 867 (2002).

    Article  CAS  Google Scholar 

  39. M. Erbeldinger, A. J. Mesiano and A. J. Russel, Biotechnol. Prog., 16, 1129 (2000).

    Article  CAS  Google Scholar 

  40. D.M. Anderson, Patent WO000057-A1 (2003).

  41. P. T. Spicer, W. B. Small and M. L. Lynch, Patent WO066014-A2 (2002).

  42. J. L. Kaar, A. M. Jesionowski, J. A. Berberich, R. Moulton and A. J. Russell, J. Am. Chem. Soc., 125, 4125 (2003).

    Article  CAS  Google Scholar 

  43. P. Lozano, T. De Diego, D. Carrie, M. Vaultier and J. L. Iborra, Biotechnol. Lett., 23, 1529 (2001).

    Article  CAS  Google Scholar 

  44. R. Hagiwara and Y. Ito, J. Fluorine Chem., 105, 221 (2000).

    Article  CAS  Google Scholar 

  45. J.G. Huddleston, A. E. Visser, W. M. Reichert, H.D. Willauer, G. A. Broker and R. D. Rogers, Green Chem., 3, 156 (2001).

    Article  CAS  Google Scholar 

  46. Z.B. Zhou, H. Matsumoto and K. Tatsumi, Chem. Eur. J., 11, 752 (2005).

    Article  CAS  Google Scholar 

  47. P. Lozano, T. De Diego, D. Carrie, M. Vaultier and J. L. Iborra, Chem. Commun., 692 (2002).

  48. M. T. Reetz, W. Wiesenhofer, G. Francio and W. Leitner, Chem. Commun., 992 (2002).

  49. T. Itoh, E. Akasaki, K. Kudo and S. Shirakami, Chem. Lett., 30, 262 (2001).

    Article  Google Scholar 

  50. T. Itoh, Y. Nishimura, N. Ouchi and S. Hayase, J. Mol. Catal. B: Enzym., 26, 41 (2003).

    Article  CAS  Google Scholar 

  51. T. Itoh, E. Akasaki and Y. Nishimura, Chem. Lett., 31, 154 (2002).

    Article  Google Scholar 

  52. J. Howarth, P. James and J. Dai, Tetrahedron Lett., 42, 7517 (2001).

    Article  CAS  Google Scholar 

  53. A. J. Carmichael and K.R. Seddon, J. Phys. Org. Chem., 13, 591 (2000).

    Article  CAS  Google Scholar 

  54. S. N.V. K. Aki, J. F. Brennecke and A. Samanta, Chem. Commun., 413 (2001).

  55. C. Reichardt, Chem. Rev., 94, 2319 (1994).

    Article  CAS  Google Scholar 

  56. J. Mutschler, T. Rausis, J.-M. Bourgeois, C. Bastian, D. Zufferey, I. V. Mohrenz and F. Fischer, Green Chem., 11, 1793 (2009).

    Article  CAS  Google Scholar 

  57. H. Zhao, O. Olubajo, Z. Song, A. L. Sims, T. E. Person, R. A. Lawal and L. A. Holley, Bioorg. Chem., 34, 15 (2006).

    Article  CAS  Google Scholar 

  58. S. Zhu, Y. Wu, Q. Chen, Z. Yu, C. Wang, S. Jin, Y. Ding and G. Wu, Green Chem., 8, 325 (2006).

    Article  CAS  Google Scholar 

  59. R. C. Remsing, R. P. Swatloski, R. D. Rogers and G. Moyna, Chem. Commun., 1271 (2006).

  60. M.B. Turner, S. K. Spear, J.G. Huddleston, J. D. Holbrey and R. D. Rogers, Green Chem., 5, 443 (2003).

    Article  CAS  Google Scholar 

  61. S. H. Lee, S. H. Ha, S. B. Lee and Y.-M. Koo, Biotechnol. Lett., 28, 1335 (2006).

    Article  CAS  Google Scholar 

  62. D.W. Armstrong, L. He and Y. S. Liu, Anal. Chem., 71, 3873 (1999).

    Article  CAS  Google Scholar 

  63. W.-Y. Lou, M.-H. Zong, H. Wu, R. Xu and J.-F. Wang, Green Chem., 7, 500 (2005).

    Article  CAS  Google Scholar 

  64. R. M. Lau, M. J. Sorgedrager, G. Carrea, F. van Rantwijk, F. Secundo and R. A. Sheldon, Green Chem., 6, 483 (2004).

    Article  Google Scholar 

  65. Q. Liu, M. H. A. Janssen, F. van Rantwijk and R.A. Sheldon, Green Chem., 7, 39 (2005).

    Article  CAS  Google Scholar 

  66. S.A. Forsyth, D.R. MacFarlane, R. J. Thomson and M. von Itzstein, Chem. Commun., 714 (2002).

  67. H. Zhao, G. A. Baker, Z. Song, O. Olubajo, T. Crittle and D. Peters, Green Chem., 10, 696 (2008).

    Article  CAS  Google Scholar 

  68. A. R. Toral, A. P. de los Rios, F. J. Hernandez, M. H. A. Janssen, R. Schoevaart, F. van Rantwijk and R. A. Sheldon, Enzyme Microb. Technol., 40, 1095 (2007).

    Article  CAS  Google Scholar 

  69. H. Zhao, G. A. Baker, Z. Song, O. Olubajo, L. Zanders and S. M. Campbell, J. Mol. Catal. B: Enzyme, 57, 149 (2009).

    Article  CAS  Google Scholar 

  70. H. Zhao, C. L. Jones and J. V. Cowins, Green Chem., 11, 1128 (2009).

    Article  CAS  Google Scholar 

  71. F. J. Hernandez-Fernandez, A. P. de los Rios, F. Tomas-Alonso, D. Gomez and G. Villora, Can. J. Chem. Eng., 87, 910 (2009).

    Article  CAS  Google Scholar 

  72. R. Irimescu and K. Kato, J. Mol. Catal. B: Enzym., 30, 189 (2004).

    Article  CAS  Google Scholar 

  73. S. H. Lee, Y.-M. Koo and S.H. Ha, Korean J. Chem. Eng., 25, 1456 (2008).

    Article  CAS  Google Scholar 

  74. H. Zhao, J. Mol. Catal. B: Enzyme, 37, 16 (2005).

    Article  CAS  Google Scholar 

  75. H. Zhao, S. Campbell, L. Jackson, Z. Song and O. Olubajo, Tetrahedron Asym., 17, 377 (2006).

    Article  CAS  Google Scholar 

  76. H. Zhao, J. Chem. Technol. Biotechnol., 81, 877 (2006).

    Article  CAS  Google Scholar 

  77. K. Fujita, D.R. MacFarlane, M. Forsyth, M. Yoshizawa-Fujita, K. Murata, N. Nakamura and H. Ohno, Biomacromolecules, 8, 2080 (2007).

    Article  CAS  Google Scholar 

  78. D. Constantinescu, H. Weingartner and C. Herrmann, Angew. Chem. Int. Ed., 46, 8887 (2007).

    Article  CAS  Google Scholar 

  79. N. Kaftzik, P. Wasserscheid and U. Kragl, Org. Process Res. Dev., 6, 553 (2002).

    Article  CAS  Google Scholar 

  80. M. Lang, T. Kamrat and B. Nidetzky, Biotechnol. Bioeng., 95, 1093 (2006).

    Article  CAS  Google Scholar 

  81. Z. Yang, J. Biotechnol., 144, 12 (2009).

    Article  CAS  Google Scholar 

  82. Z. Yang, Y.-J. Yue, W.-C. Huang, X.-M. Zhuang, Z.-T. Chen and M. Xing, J. Biochem., 145, 355 (2009).

    Article  CAS  Google Scholar 

  83. F. van Rantwijk, R.M. Lau and R. A. Sheldon, Trends Biotechnol., 21, 131 (2003).

    Article  Google Scholar 

  84. C. Laane, S. Boeren and K. Vos, Trends Biotechnol., 3, 251 (1985).

    Article  CAS  Google Scholar 

  85. C Laane, S. Boeren, K. Vos and C. Veeger, Biotechnol. Bioeng., 30, 81 (1987).

    Article  CAS  Google Scholar 

  86. S. J. Nara, J. R. Harjani and M. M. Salunkhe, Tetrahedron Lett., 43, 2979 (2002).

    Article  CAS  Google Scholar 

  87. K. Nakashima, J. Okada, T. Maruyama, N. Kamiya and M. Goto, Sci. Technol. Adv. Mat., 7, 692 (2006).

    Article  CAS  Google Scholar 

  88. K. Nakashima, T. Maruyama, N. Kamiya and M. Goto, Org. Biomol. Chem., 4, 3462 (2006).

    Article  CAS  Google Scholar 

  89. W.-G. Zhang, D.-Z. Wei, X.-P. Yang and Q.-X. Song, Bioprocess Biosyst. Eng., 29, 379 (2006).

    Article  CAS  Google Scholar 

  90. W.-Y. Lou and M.-H. Zong, Chirality, 18, 814 (2006).

    Article  CAS  Google Scholar 

  91. M. Paljevac, M. Habulin and Z. Knez, Chem. Ind. Chem. Eng. Q., 12, 181 (2006).

    Article  CAS  Google Scholar 

  92. A. P. de los Rios, F. J. Hernandez-Fernandez, M. Rubio, D. Gomez and G. Villora, J. Chem. Technol. Biotechnol., 82, 190 (2007).

    Article  Google Scholar 

  93. A. P. de los Rios, F. J. Hernandez-Fernandez, F. A. Martinez, M. Rubio and G. Villora, Biocatal. Biotransform., 25, 151 (2007).

    Article  Google Scholar 

  94. S. H. Ha, S. H. Lee, D. T. Dang, M. S. Kwon, W.-J. Chang, Y. J. Yu, I. S. Byun and Y.-M. Koo, Korean J. Chem. Eng., 25, 291 (2008).

    Article  CAS  Google Scholar 

  95. Z.-L. Shen, W. J. Zhou, Y.-T. Liu, S.-J. Ji and T.-P. Loh, Green Chem., 10, 283 (2008).

    Article  CAS  Google Scholar 

  96. K. Ryu and J. S. Dordick, Biochemistry, 31, 2588 (1992).

    Article  CAS  Google Scholar 

  97. R.M. Lau, F. van Rantwijk, K.R. Seddon and R.A. Sheldon, Org. Lett., 2, 4189 (2000).

    Article  CAS  Google Scholar 

  98. T. Itoh, Y. Nishimura, M. Kashiwagi and M. Onaka, in Ionic liquids as green solvents: Progress and prospects, R. D. Rogers and K. R. Seddon Eds., American Chemical Society, Washington DC (2003).

    Google Scholar 

  99. N. Kaftzik, S. Neumann, M.-R. Kula and U. Kragl, in Ionic liquids as green solvents: Progress and prospects, R. D. Rogers and K. R. Seddon Eds., American Chemical Society, Washington DC (2003).

    Google Scholar 

  100. P. Lozano, T. de Diego, D. Carrie, M. Vaultier and J. L. Iborra, in Ionic liquids as green solvents: Progress and prospects, R. D. Rogers and K.R. Seddon Eds., American Chemical Society, Washington DC (2003).

    Google Scholar 

  101. M. Eckstein, P. Wasserscheid and U. Kragl, Biotechnol. Lett., 24, 763 (2002).

    Article  CAS  Google Scholar 

  102. A. Basso, S. Cantone, P. Linda and C. Ebert, Green Chem., 7, 671 (2005).

    Article  CAS  Google Scholar 

  103. U. Schroder, J.D. Wadhawan, R.G. Compton, F. Marken, P.A. Z. Suarez, C. S. Consorti, R. F. de Souza and J. Dupont, News J. Chem., 24, 1009 (2000).

    Article  CAS  Google Scholar 

  104. J. Dupont, J. Brazil Chem. Soc., 15, 341 (2004).

    Article  CAS  Google Scholar 

  105. T. L. Greaves and C. J. Drummond, Chem. Soc. Rev., 37, 1709 (2008).

    Article  CAS  Google Scholar 

  106. Z. Qiu and J. Texter, Curr. Opin. Colloid Interface Sci., 13, 252 (2008).

    Article  CAS  Google Scholar 

  107. G. Savelli, N. Spreti and P. Di Profio, Curr. Opin. Colloid Interface Sci., 5, 111 (2000).

    Article  CAS  Google Scholar 

  108. N. Spreti, A. Bartoletti, P. Di Profio, R. Germani and G. Savelli, Biotechnol. Prog., 11, 107 (1995).

    Article  CAS  Google Scholar 

  109. Z. Yang, J. Deng and L.-F. Chen, J. Mol. Catal. B: Enzyme, 47, 79 (2007).

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemical Engineering and Nano-Bio Technology, Hannam University, Daejeon, 305-811, Korea

    Sung Ho Ha

  2. Department of Biological Engineering, Inha University, Incheon, 402-751, Korea

    Yoon-Mo Koo

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  1. Sung Ho Ha
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Correspondence to Yoon-Mo Koo.

Additional information

This article has been retracted. The corresponding author failed to check raw materials collected by his students. Therefore, a large portion of this review paper is a direct copy of a previously published other review paper. The corresponding author deeply regrets the uncareful checking and publication.

Yoon-Mo Koo is a Professor in the Department of Chemical and Biological Engineering at Inha University, Korea. He received B.S. degree (Seoul National University, Korea), M.S. degree (KAIST, Korea), and Ph.D. degree (Purdue University) all in Chemical Engineering. He served as the Dean of College of Engineering, Inha University, the President of the Korean Society of Biotechnology and Bioengineering, and is currently a Member of the National Academy of Engineering, Korea. His research interests include biological separation and purification, microbial mixed culture, and ionic liquids.

An erratum to this article is available at http://dx.doi.org/10.1007/s11814-013-0016-9.

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Ha, S.H., Koo, YM. RETRACTED ARTICLE: Enzyme performance in ionic liquids. Korean J. Chem. Eng. 28, 2095–2101 (2011). https://doi.org/10.1007/s11814-011-0268-1

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