LIPASE CATALYZED PARALLEL KINETIC RESOLUTION OF IBUPROFEN
Keywords:
lipase, Ibuprofen, enzymatic kinetic resolution, stereoselectivityAbstract
A series of commercially available lipases in various solvents using several alcohols as nucleophiles were studied for the stereoselective esterification of ibuprofen and alcoholysis of ibuprofen esters respectively. Novel methods were developed for the stereoselective synthesis of both enantiomers of the target compound. The (S)-selective alcoholysis and (R)-selective hydrolysis in a parallel kinetic resolution procedure in presence of lipase from Mucor miehei as catalyst were performed.
References
K.M. Williams, R.O. Day, R.D. Knihinicki, A.M. Duffield, Acta Pharm. Toxicol. 1986, 59, 192.
R.H. Sonawane, N.S. Bellur, J.R. Ahuja, Tetrahedron:Asymmetry 1992, 3, 163.
Y. Maryam; M. Mehdi, H. Zohreh, J. Mol. Catal. B: Enzym. 2014, 104, 87.
F. Roure, A. Ducret, M. Trani, R. Lortie, J. Chem. Tech. Biotechnol. 1997, 69, 266; S.W. Tsai, J.J. Lin, C.S. Chang, J.P. Chen, Biotechnol. Prog. 1997, 13, 82; D. Chavez-Flores, J.M. Salvador, Tetrahedron: Asymmetry 2012, 23, 237.
C. Jose, M.V. Toledo, L.E. Briand, Crit. Rev. Biotechnol. 2016, 36(5), 891; V. Gotor-Fernandez, E. Busto, V. Gotor, Adv. Synth. Catal. 2006, 348, 797; A.K. Prasad, M. Husain, B.K. Singh, R.K. Gupta, V.K. Manchanda, C.E. Olsen, V.S. Parmar, Tetrahedron Lett. 2005, 46, 4511.
R. Morrone, N. D’Antona, D. Lambusta, G. Nicolosi, J. Mol. Catal. B: Enzym. 2010, 65, 49.
A.C. Wu, P.Y. Wang, Y.S. Lin, M.F. Kao, J.R. Chen, J.F. Ciou, S.W. Tsai, J. Mol. Catal. B: Enzym. 2010, 62, 235.
W. Tsuzuki, A. Ue, A. Nagao Biosci. Biotechnol. Biochem. 2003, 67, 1660.
Chen. J.P., Wang, J.B. Enzyme Microb. Technol. 1997, 20, 615; Chulalaksananukul, W., Condoret, J.S., Combes, D. Enzyme Microb. Technol. 1993, 15, 691.
For examples: J. Brem, M. Naghi, M.I. Tosa, Z. Boros, L. Poppe, F.D. Irimie, C. Paizs, Tetrahedron: Asymmetry 2011, 22, 1672; M. Liaquat, J. Mol. Catal. B: Enzym. 2011, 68, 59; T. Miyazawa, E. Kaito, T. Yukawa, T. Murashima, T.; Yamada, J. Mol. Catal. B: Enzym. 2005, 37, 63; E. Santaniello, S. Casati, P. Ciuffreda, G. Meroni, A. Pedretti, G. Vistoli, Tetrahedron: Asymmetry 2009, 20, 1833; K, Kaewprapan, J. Wongkongkatep, W. Panbangred, P. Phinyocheep, E. Marie, A. Durand, P. Inprakhon, J. Biosci. Bioeng. 2011, 112(2), 124.
C. Blecker; S. Danthine; M. Pétré; G. Lognay; B. Moreau; L.V. Elst; M. Paquot; C. Deroanne J. Colloid Interf. Sci. 2008, 321, 154.
C. Torres; C. Otero Enzyme Microb. Technol. 1999, 25, 745.
A. Ghanem, H.Y. Aboul-Enein, Chirality 2005, 17(1),1; R.D. Schmid, R.A. Verger, Angew. Chem. Int. Edit. 1998, 37, 1608; V.B. Gotor Med. Chem. 1999, 7, 2189, U.T. Bornscheuer, R. J. Kazlauskas Hydrolases in Organic Synthesis, Wiley–VCH, 1999
A. Torres-Gavilán, E. Castillo, A. López-Munguía, J. Mol. Catal. B: Enzym. 2006, 41, 136.
R. Gandolfi, R. Gualandris, Ch. Zanchi, F. Molinari, Tetrahedron: Asymmetry, 2001, 12, 501; A. Romano, R. Gandolfi, F. Molinari, A. Converti, M. Zilli, M. Del Borghi, Enzyme Microb. Technol. 2005, 36, 432.
K. Engström, J. Nyhlen, A.G. Sandström, J.E. Backväll, J. Am. Chem. Soc. 2010, 132, 7038; A. G. Sandström, K. Engström; J. Jyhlen; A. Kasrayan; J.E. Bäckvall, Protein Eng., Des. Sel. 2009, 22, 413.
P. Spizzo, A. Basso, C. Ebert, L. Gardossi, V. Ferrario, D. Romano, F. Molinari, Tetrahedron 2007, 63, 11005.
C.-S. Chen, Y. Fujimoto, G. Girdaukas, C.J. Sih, J. Am. Chem. Soc. 1982, 104, 7294.
C.W. Lee, H. Alper, J. Org. Chem. 1995 , 60, 250; S. Koul, J.L. Koul, B. Singh, M. Kapoor, R. Parshad, K.S Manhas, S.C. Taneja, G.N. Qazi, Tetrahedron: Asymmetry 2005, 16, 2575; A.K. Bansal, R.K. Khar, R. Dubey, A.K. Sharma, Pharmazie 1994, 49, 422; M. Kapoor, R. Parshad, K.S. Manhas, S.C. Taneja, G.N. Qazi, Tetrahedron: Asymmetry 2005, 16, 2575, A.K. Bansal, R.K. Khar, R. Dubey, A.K. Sharma, Pharmazie 1994, 49, 422.
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