[en] tKinetic resolution of d,l-ethyl lactate (d,l-LA-Et) and d,l-butyl lactate (d,l-LA-Bu) was accomplished inthe presence of lipases. Transesterification of the lactate esters with alcohols was shown to be poorlyenantioselective, with a very low preference toward the l enantiomer. However, esterification of the freehydroxyl function of the lactate esters was much more enantioselective, with an opposite preferencetoward the d form. Among the 200 combinations screened (substrates and lipases), only two reactionsfulfilled the required criteria for an efficient resolution (fast reaction, enantioselectivity ratio higherthan 100). The best resolution was obtained by esterification of d,l-LA-Bu with butyric anhydride inthe presence of lipase B from Candida antarctica (CAL-B) in heptane (at 30◦C): LA-Bu was resolved in6 h with an initial esterification rate of d-LA-BU of 1.5 g L−1h−1g−1EZ, an enantioselectivity ratio higherthan 100, a l substrate consumption lower than 1%, and a final substrate enantiomeric excess superiorto 99%. After having demonstrated that neither LA-Bu nor BuAn were inhibitors of CAL-B, the reactionwas further improved by carrying it out in a solvent free system, at an elevated temperature (60◦C), andat a higher lipase concentration. LA-Bu was resolved in 6 h with an initial rate of 7.6 g L−1h−1g−1EZ, anenantioselectivity ratio higher than 100, and a final substrate enantiomeric excess of 95%.
Disciplines :
Food science
Author, co-author :
Richard, Gaetan ; Université de Liège - ULiège > Chimie et bio-industries > Analyse, qual. et risques - Labo. de Chimie analytique
Nott, Katherine ; Université de Liège - ULiège > Chimie et bio-industries > Chimie biologique industrielle
Nicks, François
Paquot, Michel ; Université de Liège - ULiège > Chimie et bio-industries > Chimie biologique industrielle
Blecker, Christophe ; Université de Liège - ULiège > Chimie et bio-industries > Science des alim. et formul.
Fauconnier, Marie-Laure ; Université de Liège - ULiège > Chimie et bio-industries > Chimie générale et organique
Language :
English
Title :
Use of lipases for the kinetic resolution of lactic acid esters in heptane or in a solvent free system
K. Ishimoto, M. Arimoto, H. Ohara, S. Kobayashi, M. Ishii, K. Morita, H. Yamashita, and N. Yabuuchi Biomacromolecules 10 2009 2719 2723
B. Gupta, N. Revagade, and J. Hilborn Progress in Polymer Science 32 2007 455 482
R. Auras, B. Harte, and S. Selke Macromolecular Bioscience 4 2004 835 864
O. Dechy-Cabaret, B. Martin-Vaca, and D. Bourissou Chemical Reviews 104 2004 6147 6176
G. Perego, and G.D. Cella R. Auras, L.-T. Lim, S. E. M. Selke, H. Tsuji, Mechanical Properties, in Poly(Lactic Acid): Synthesis, Structures, Properties, Processing, and Applications 2010 John Wiley & Sons, Inc. Hoboken, NJ, USA 10.1002/9780470649848.ch11
T. Miyazawa, E. Kaito, T. Yukawa, T. Murashima, and T. Yamada Journal of Molecular Catalysis B: Enzymatic 37 2005 63 67
Y. Wang, R. Wang, Q. Li, Z. Zhang, and Y. Feng Journal of Molecular Catalysis B: Enzymatic 56 2009 142 145
N. Bouzemi, H. Debbeche, L. Aribi-Zouioueche, and J.-C. Fiaud Tetrahedron Letters 45 2004 627 630
V. Gotor-Fernández, R. Brieva, and V. Gotor Journal of Molecular Catalysis B: Enzymatic 40 2006 111 120
H. Ismail, R.M. Lau, F. van Rantwijk, and R.A. Sheldon Advanced Synthesis and Catalysis 350 2008 1511 1516
C. Inaba, K. Maekawa, H. Morisaka, K. Kuroda, and M. Ueda Applied Microbiology and Biotechnology 83 2009 859 864
P. Hadik, L. Kotsis, M. Eniszné-Bódogh, and L.-P.E Szabó Nagy Separation and Purification Technology 41 2005 299 304
S. Hasegawa, M. Azuma, and K. Takahashi Journal of Chemical Technology and Biotechnology 83 2008 1503 1510
D. Pirozzi, and G. Greco Jr. Enzyme and Microbial Technology 34 2004 94 100
D. Pirozzi, and G. Greco Jr. Biotechnology Progress 22 2006 444 448
S. Hasegawa, M. Azuma, and K. Takahashi Enzyme and Microbial Technology 43 2008 309 316
H. Ohara, A. Onogi, M. Yamamoto, and S. Kobayashi Biomacromolecules 11 2010 2008 2015
A.J.J. Straathof, and J.A. Jonhejan Enzyme and Microbial Technology 21 1997 559 571
K.J. Patile, M.Z. Chopda, and R.T. Mahajan Indian Journal of Science and Technology 4 2011 971 982
I.A. Shuklov, N.V. Dubrovina, J. Schulze, W. Tietz, K. Kühlein, and A. Börner Tetrahedron letters 53 2012 6326 6328
N.N. Gandhi Journal of the American Oil Chemists' Society 74 1997 621 634
A.M. Gumel, M.S.M. Annuar, T. Heidelberg, and Y. Chisti Process Biochemistry 46 2011 2079 2090
M. From, P. Adlercreutz, and B. Mattiasson Biotechnology Letters 19 1997 315 318
T. Ema, S. Maeno, Y. Takaya, T. Sakai, and M. Utaka Tetrahedron: Asymmetry 7 1996 625 628
C. Torres, and C. Otero Enzyme and Microbial Technology 29 2001 3 12
A. Córdova, T. Iversen, and K. Hult Macromolecules 31 1998 1040 1045
J.-H. Sun, R.-J. Dai, W.-W. Meng, and Y.-l. Deng Catalysis Communications 11 2010 987 991
R.J. Kazlauskas, A.N.E. Weissfloch, A.T. Rappaport, and L.A. Cuccia Journal of Organic Chemistry 56 1991 2656 2665
K. Miyazawa, N. Yoshida, 1991, US 5248610.
B.K. Pchelka, A. Loupy, J. Plenkiewicz, and L. Blanco Tetrahedron: Asymmetry 11 2000 2719 2732
D. Guieysse, C. Salagnad, P. Monsan, and M. Remaud-Simeon Tetrahedron: Asymmetry 12 2001 2473 2480