Double Immobilized Lipase For The Kinetic Resolution Of Secondary Alcohols
Sol-gel immobilization of enzymes, which can improve considerably their properties, is now one of the most used techniques. By deposition of the entrapped lipase on a solid support, a new and improved biocatalyst was obtained, which can be used with excellent results in acylation reactions. In this...
| Main Authors: | , , , , |
|---|---|
| Format: | Text |
| Language: | English |
| Published: |
Zenodo
2011
|
| Subjects: | |
| Online Access: | https://dx.doi.org/10.5281/zenodo.1077344 https://zenodo.org/record/1077344 |
| Summary: | Sol-gel immobilization of enzymes, which can improve considerably their properties, is now one of the most used techniques. By deposition of the entrapped lipase on a solid support, a new and improved biocatalyst was obtained, which can be used with excellent results in acylation reactions. In this paper, lipase B from Candida antarctica was double immobilized on different adsorbents. These biocatalysts were employed in the kinetic resolution of several aliphatic secondary alcohols in organic medium. High total recovery yields of enzymatic activity, up to 560%, were obtained. For all the studied alcohols the enantiomeric ratios E were over 200. The influence of the reaction medium was studied for the kinetic resolution of 2-pentanol. : {"references": ["T. Raghavendra, D. Sayania, and D. Madamwar, \"Synthesis of the\n\"green apple ester\" ethyl valerate in organic solvents by Candida rugosa\nlipase immobilized in MBGs in organic solvents: Effects of\nimmobilization and reaction parameters\", Journal of Molecular\nCatalysis B: Enzymatic, vol. 63, 2010, pp. 31-38.", "Y. Mine, L. Zhang, K. Fukunaga, and Y. Sugimura, \"Enhancement of\nenzyme activity and enantioselectivity by cyclopentyl methyl ether in the\ntransesterification catalyzed by Pseudomonas cepacia lipase colyophilized\nwith cyclodextrins\", Biotechnology Letters, vol. 27, 2005,\npp. 383-388.", "A. G. Cunha, A. T. da Silva, A. J. R. da Silva, L. W. Tinoco, R. V.\nAlmeida, R. B. de Alencastro, A. B. C. Simas, and D. M. G. Freire,\n\"Efficient kinetic resolution of (\u252c\u2592)-1,2-O-benzyl-myo-inositol with the\nlipase B of Candida antarctica\", Tetrahedron: Asymmetry, vol. 21,\n2010, pp. 2899-2903.", "J. H. Lee, K. Han, M.-J. Kim, and J. Park, \"Chemoenzymatic Kinetic\nResolution of Alcohols and Amines\", European Journal of Organic\nChemistry, 2010, pp. 999-1015.", "V. Gotor-Fernandez, R. Brieva, and V.Gotor, \"Useful biocatalysts for\nthe preparation of pharmaceuticals\", Journal of Molecular Catalysis B:\nEnzymatic, vol. 40, 2006, pp. 111-120.", "H.-M. Chen, P.-Y. Wang, and S.-W. Tsai, \"Carica papaya lipasecatalyzed\ntransesterification resolution of secandary alcohols in organic\nsolvents\", Journal of the Taiwan Institute of Chemical Engineers, vol.\n40, 2009, pp. 594-554.", "A. Tomin, D. Weiser, G. Hellner, Z. Bata, L. Cor\u251c\u00abci, F. P\u00e9ter, B. Koczka,\nand L. Poppe, \"Fine-tuning the second generation sol-gel lipase\nimmobilization with ternary alkoxysilane precursor systems\", Process\nBiochemistry, vol. 46, 2011, pp. 52-58.", "N. Kharrat, Y. B. Ali, S. Marzouk, Y.-T. Gargouri, and M. Karra-\nChaabouni, \"immobilization of Rhizopus oryzae Lipase on silica\naerogels by adsorption: Comparison with free enzyme\", Process\nBiochemistry, 2011, doi:10.1016/j.procbio.2011.01.029.", "F. Peter, L. Poppe, C. Kiss, E. Szocs-Biro, G. Preda, C. Zarcula, and A.\nOlteanu, \u00d4\u00c7\u00d7Influence of precursors and additives on microbial lipases\nstabilized by sol-gel entrapment\", Biocat. Biotrans., vol. 23, nr. 3/4,\n2005, pp. 251-260.\n[10] C. Zarcula, L. Cor\u251c\u00abci, R. Croitoru, A. Ursoiu, and F. P\u00e9ter, \"Preparation\nand properties of xerogels obtained by ionic liquid incorporation during\nthe immobilization of lipase by the sol-gel method\", Journal of\nMolecular Catalysis B: Enzymatic, vol. 65, 2010, pp. 79-86.\n[11] A. Uyanik, N. Sen, and M. Yilmaz, \"Improvement of catalytic activity of\nlipase from Candida rugosa via sol-gel encapsulation in the presence of\ncalix(aza)crown\", Bioresource Technology, 2011, doi:\n10.1016/j.biortech.2010.12.105.\n[12] F. P\u00e9ter, C. Paul, and A. Ursoiu, \"Application of ionic liquids to increase\nthe efficiency of lipase biocatalysis\", in \"Ionic Liquids: Applications and\nPerspectives\", edited by Alexander Kokorin, 2011, ISBN: 978-953-307-\n248-7, under publishing.\n[13] C. Mateo, J. M. Palomo, G. Fernandez-Lorente, J. M. Guisan, and R.\nFernandez-Lafuente, \"Improvement of enzyme activity, stability and\nselectivity via immobilization techniques\", Enzyme and Microbial\nTechnology, vol. 40, 2007, pp. 1451-1463.\n[14] H. P. Heldt-Hansen, M. Ishii, S. A. Patkar, T. T. Hansen, and P. Eigtved,\n\"A new immobilized positional nonspecific lipase for fat modification\nand ester synthesis\", ACS Symposium Series, vol. 389, 1989, pp. 158-\n172.\n[15] L. Brady, A. M. Brzozowski, Z. S. Derewenda, E. Dodson, G. Dodson,\nS. Tolley, J.P. Turkenburg, L. Christiansen, B. Huge-Jensen, L.\nNorskov, L. Thim, and U. Menge, \"A serine protease triad forms the\ncatalytic centre of a triacylglycerol lipase\", Nature, vol. 343, 1990, pp.\n767-770.\n[16] C.-S. Chen, Y. Fujimoto, G. Girdauskas, and C. J. Sih, \"Quantitative\nanalyses of biochemical kinetic resolutions of enantiomers\", Journal of\nthe American Chemical Society, vol. 104, 1982, pp. 7294-7299.\n[17] D. Zelaszczyk, and K. Kiec-Konowicz, \"Biocatalytic Approaches to\nOptically Active \u03b2-Blockers\", Current Medicinal Chemistry, vol. 14,\n2007, pp. 53-65\n[18] A. Ursoiu, C. Paul, C. Marcu, T. P\u00e9ter, and F. P\u00e9ter, \"Binary and\nternanry silane precursor systems for immobilization of lipases\", Annals\nof West University of Timisoara, vol. 16, no. 2, 2010, pp. 17-22.\n[19] C. Reichardt, \"Solvatochromic Dyes as Solvent Polarity Indicators\",\nChem. Rev., vol. 94, 1994, pp. 2319-2358."]} |
|---|