Abstract
The resolution of (R,S)-2-octanol catalyzed by magnetite-immobilized Yarrowia lipolytica lipase in ionic liquids was investigated. The optimal activity and enantioselectivity of the lipase were obtained in a mixture of [EMIM]BF4 and [OMIM]BF4 (v/v = 5:5). Excellent reusability of the enzyme-ionic liquid system was observed in consecutive batch reactions.
Graphical Abstract
Similar content being viewed by others
References
Patel RN (2001) Curr Opin Biotechnol 12:587
Dai DZ, Xia LM (2006) Appl Biochem Biotechnol 134:39
Brennecke JF, Maginn EJ (2001) AIChE J 47:2384
Van Rantwijk F, Sheldon RA (2007) Chem Rev 107:2757
Earle MJ, Esperanca JMSS, Gilea MA, Lopes JNC, Rebelo LPN, Magee JW, Seddon KR, Widegren JA (2006) Nature 439:831
Dhake KP, Qureshi ZS, Singhal RS, Bhanage BM (2009) Tetrahedron Lett 50:2811
Erbeldinger M, Mesiano AJ, Russell AJ (2000) Biotecnol Prog 16:1129
Eckstein M, Filho MV, Liesec A, Kragl U (2004) Chem Commun 1084
Hinckley G, Mozhaev VV, Budde C, Khmelnitsky YL (2002) Biotechnol Lett 24:2083
Lau RM, Van Rantwijk F, Seddon KR, Sheldon RA (2000) Org Lett 2:4189
Schofer SH, Kaftzik N, Wasserscheid P, Kragl U (2001) Chem Commun 425
Itoh T, Akasaki E, Kudo K, Shirakami S (2001) Chem Lett 3:262
Itoh T, Nishimura Y, Ouchi N, Hayase S (2003) J Mol Catal B 26:41
Kaar JL, Jesionowski AM, Berberich JA, Moulton R, Russell AJ (2003) J Am Chem Soc 125:4125
Lau RM, Sorgedrager MJ, Carrea G, Van Rantwijk F, Secundo F, Sheldon RA (2004) Green Chem 6:483
Lee SH, Dang DT, Ha SH, Chang WJ, Koo YM (2008) Biotechnol Bioeng 99:1
De Diego T, Lozano P, Abad MA, Steffensky K, Vaultier M, Iborra JL (2009) J Biotechnol 140:234
Vidya P, Chadha A (2009) J Mol Catal B 57:145
Ottosson J, Fransson L, King JW, Hult K (2002) Biochim Biophys Acta 1594:325
Lozano P, De Diego T, Gmouh S, Vaultier M, Iborra JL (2005) Biocatal Biotransform 23:169
Park S, Kazlauskas RJ (2001) J Org Chem 66:8395
Liu Y, Guo C, Sun XT, Liu CZ (2013) Bioresour Technol 142:415
Liu Y, Guo C, Liu CZ (2014) J Mol Catal B 101:23
Chen CS, Fujimoto Y, Girdaukas G, Sih CJ (1982) J Am Chem Soc 104:7294
Sheldon RA, Madeira LR, Sorgedrager MJ, Van Rantwijk F, Seddon KR (2002) Green Chem 4:147
Gorke JT, Okrasa K, Louwagie A, Kazlauskas RJ, Srienc F (2007) J Biotechnol 132:306
Irimescu R, Kato K (2004) Tetrahedron Lett 45:523
Quiroga E, Cami G, Marchese J, Barberis S (2007) Biochem Eng J 35:198–202
Anderson JL, Ding J, Welton T, Armstrong DW (2002) J Am Chem Soc 124:14247
Jiang YY, Guo C, Gao HS, Xia HS, Mahmood I, Liu CZ, Liu HZ (2012) AIChE J 58:1203
Lozano P, De Diego T, Sauer T, Vaultier M, Gmouh S, Iborra JL (2007) J Supercrit Fluids 40:93
Luetz S, Giver L, Lalonde J (2008) Biotechnol Bioeng 101:647
Lee SH, Ha SH, Hiep NM, Chang WJ, Koo YM (2008) J Biotechnol 133:486
Acknowledgments
The work was financially supported by the National Basic Research Program of China (No. 2013CB733600), the National Natural Science Foundation of China (No. 21176241) and the Key Deployment Program of Chinese Academy of Sciences (KSZD-EW-Z-015). We thank Dr. Amanda Stiles (the Chinese Academy of Sciences Fellowships for Young International Scientists, No. 2011Y1GA01) for helping to edit this manuscript.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Liu, Y., Guo, C. & Liu, CZ. Efficient Kinetic Resolution of (R,S)-2-Octanol Catalyzed by Magnetite-Immobilized Yarrowia lipolytica Lipase in Mixed Ionic Liquids. Catal Lett 144, 1552–1556 (2014). https://doi.org/10.1007/s10562-014-1303-8
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10562-014-1303-8