Influence of ionic liquids under controlled water activity and low halide content on lipase activity

Sang Hyun Lee; Yoon-Mo Koo; Sung Ho Ha

Korean Journal of Chemical Engineering, Vol.25, No.6, 1456-1462, November, 2008

DOI10.1007/s11814-008-0239-3 Export Citation

Influence of ionic liquids under controlled water activity and low halide content on lipase activity

Sang Hyun Lee¹, Yoon-Mo Koo^{1, 2}, and Sung Ho Ha^{1, †}

¹ERC for Advanced Bioseparation Technology, Inha University, Incheon 402-751, Korea
²Department of Biological Engineering, Inha University, 402-751, Korea

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Room-temperature ionic liquids (ILs) can be used as reaction media for nonaqueous biocatalysis. However, the purity of ILs should be considered to understand the influence of ILs on enzyme activity. The major impurities in ILs are water and halide. In the transesterification of benzyl alcohol with vinyl acetate, the optimal water activities for lipases in [Omim][Tf2N] were similar to those in organic solvents. The chloride impurity in [Omim][Tf2N] seriously influenced the activity of lipase. In this work, the effect of ILs on lipase activity was investigated under controlled initial water activity and low halide content. The activity of lipase was highly dependent upon the anion structure of ILs. The initial reaction rate of lipases followed the order [Tf2N]- >[PF6]- >[TfO]- >[SbF6]- ≒[BF4]-. All tested lipases showed the highest activities in ILs containing [Tf2N] anion. Particularly, [AAIM][Tf2N] was shown as a suitable reaction medium for biocatalysis. Lipozyme IM showed the highest activity in this IL among tested ILs. Thermal stability of lipase was also investigated. The higher thermal stability of Novozym 435 was obtained in hydrophobic and water-immiscible ILs such as [Bmim][Tf2N], [Edmim][Tf2N], and [Bmim][PF6].

Keywords:Ionic Liquid;Lipase;Transesterification;Halide;Water Activity

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[2] Sheldon RA, Lau RM, Sorgedrager MJ, van Rantwijk F, Green Chem., 4, 147 (2002)

[3] Freemantle M, Chem. Eng. News, 76(13), 32 (1998)

[4] Erbeldinger M, Mesiano AJ, Russell AJ, Biotechnol. Prog., 16(6), 1129 (2000)

[5] Park S, Kazlauskas RJ, Curr. Opin. Biotechnol., 14, 432 (2003)

[6] Schofer SH, Kaftzik NW, Wasserscheid P, Kragl U, Chem. Commun., 425 (2001)

[7] Kim KW, Song B, Choi MY, Kim MJ, Org. Lett., 3, 1507 (2001)

[8] Itoh T, Akasaki E, Kudo K, Shirakami S, Chem. Lett., 262 (2001)

[9] Won K, Lee SB, Biotechnol. Bioprocess. Eng., 7, 76 (2002)

[10] Berberich JA, Kaar JL, Russell AJ, Biotechnol. Prog., 19(3), 1029 (2003)

[11] Lee SH, Ha SH, Lee SB, Koo YM, Biotechnol. Lett., 28(17), 1335 (2006)

[12] Valivety RH, Halling PJ, Peilow AD, Macrae AR, Biochim. Biophys. Acta, 1122, 143 (1992)

[13] Chowdary GV, Prapulla SG, Process Biochem., 38, 393 (2002)

[14] Ulbert O, Belafi-Bako K, Tonova K, Gubicza L, Biocatal. Biotransform., 23, 177 (2005)

[15] Halling PJ, Enzyme Microb. Technol., 16(3), 178 (1994)

[16] Pepin P, Lortie R, Biotechnol. Bioeng., 63(4), 502 (1999)

[17] Pepin P, Lortie R, Biotechnol. Bioeng., 75(5), 559 (2001)

[18] Lue BM, Karboune S, Yeboah FK, Kermasha S, J. Chem. Technol. Biotechnol., 80(4), 462 (2005)

[19] Li XF, Lou WY, Smith TJ, Zong MH, Wu H, Wang JF, Green Chem., 8, 538 (2006)

[20] Barahona D, Pfromm PH, Rezac ME, Biotechol. Bioeng., 93, 318 (2005)

[21] Lou WY, Zong MH, Chirality, 18, 814 (2006)

[22] Halling PJ, Biotechnol. Bioeng., 35, 691 (1990)

[23] Turner MB, Spear SK, Huddleston JG, Holbrey JD, Rogers RD, Green Chem., 5, 443 (2005)

[24] Huddleston JG, Broker GA, Willauer HD, Rogers RD, Ionic Liquids ACS Symp. Ser., 818, 270 (2002)

[25] Anderson JL, Ding J, Welton T, Armstrong DW, J. Am. Chem. Soc., 124, 14245 (2002)

[26] Poole CF, J. Chromatogr. A., 1037, 49 (2004)

[27] Reichardt C, Green Chem., 7, 339 (2005)

[28] Lee SH, Biocatalysis in ionic liquids: Influence of physicochemical properties of ionic liquids on enzyme activity and enantioselectivity, PhD thesis, POSTECH (2005)

[29] Ulbert O, Frater T, Belafi-Bako K, Gubicza L, J. Mol. Catal. B: Enzym., 31, 39 (2004)

[30] Park S, Kazlauskas RJ, J. Org. Chem., 66, 8395 (2001)

[31] Kaar JL, Jesionowski AM, Berberich JA, Moulton R, Russell AJ, J. Am. Chem. Soc., 125(14), 4125 (2003)

[32] Zhao H, J. Mol. Catal. B: Enzym., 37, 16 (2005)

[33] Nurok D, Kleyle RM, Muhoberac BB, Frost MC, Hajdu P, Robertson DH, Kamat SV, Russel AJ, J. Mol. Catal. B: Enzym., 7, 273 (1999)

[34] Welton T, Chem. Rev., 99(8), 2071 (1999)

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

[36] Berger B, Faber K, J. Chem. Soc. Chem. Commun., 1198 (1991)

[37] Mizumo T, Marwanta E, Matsumi N, Ohno H, Chem. Lett., 1360 (2004)

[38] Zaks A, Klibanov AM, J. Biol. Chem., 236, 3194 (1988)

[39] Lee SH, Doan TTN, Ha SH, Koo YM, J. Mol. Catal. B: Enzym., 45, 57 (2007)