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Przemysłowe zastosowania lipaz w syntezie związków o wysokiej wartości dodanej – 85 lat katalizy enzymatycznej lipazami. Część 2

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EN
Industrial applications of lipases in the synthesis of high added-value chemicals – 85 years of lipase-based enzymatic catalysis. Part 2
Języki publikacji
PL
Abstrakty
EN
Biotransformations are processes, in which chemical reactions are catalyzed by isolated enzymes or whole cells containing them. Among the biocatalysts, lipases are the most commonly used chiral selectors that exhibit high chemo-, regio-, and stereo-selectivity toward wide spectrum of organic compounds of xenobiothic nature. Moreover, lipases are very stable and active in organic solvents, as well as in neat solvents or in supercritical fluids in the absence of added water. Biotransformations by using lipases can be carried out at high substrate concentrations, at ambient temperature and neutral pH, without need for addition of cofactors, application of high pressures, extremely harsh reaction conditions or complex chemical apparatus. In addition, processes based on efficient biocatalytic technologies has proven to be beneficial for the chemical industry, as the lipases are able to catalyze reactions, which are not easily conducted by classical methods or in other cases allow reactions, which can replace several chemical steps. The above mentioned features of lipase-based biotransformations often cause significant improvement in energy efficiency (savings), and lead to a reduction in waste generation thereby making manufacturing processes even more economically attractive and environmentally acceptable. Since the mid-1980s the use of biotransformations with lipases in industry for the production of high added-value compounds, including pharmaceuticals, vitamins, cosmetics, fragrances and flavors, diagnostic preparations and therapeutics, high-tonnage preparation of agrochemicals, modified foods, nutraceuticals, detergents, polymers, advanced materials and biofuels has steadily increased. In this part of the review article on industrial applications of lipases, next group of popularly utilized enzymes relevant for the production of high added-value chemicals are described. It was also shown on several examples that enzymatic catalysis can significantly simplify manufacturing processes of complex structures being green and economical alternative for conventional chemical-based processes. Keywords:
Rocznik
Strony
431--463
Opis fizyczny
Bibliogr. 171, rys., schem.
Twórcy
  • Politechnika Warszawska, Wydział Chemiczny, Instytut Biotechnologii, ul. Noakowskiego 3, 00-664 Warszawa
Bibliografia
  • [1] R. Gupta, A. Kumari, P. Syal, Y. Singh, Prog. Lipid Res., 2015, 57, 40.
  • [2] A. Salihu, Alam, M.Z. Process Biochem., 2015, 50, 86.
  • [3] K. Faber, Biotransformations in Organic Chemistry: a Textbook, 6th ed., SpringerVerlag, New York, NY, 2011.
  • [4] E. Su, D. Wei, J. Agric. Food Chem., 2014, 62, 6375.
  • [5] X.L. Qin, B. Yang, H.H. Huang, Y.H. Wang, J. Agric. Food Chem., 2012, 60, 2377.
  • [6] S.A. Teichert, C.C. Akoh, J. Agric. Food Chem., 2011, 59, 9588.
  • [7] I. Karabulut, G. Durmaz, A.A. Hayaloglu, J. Agric. Food Chem., 2009, 57, 10466.
  • [8] K. Sabally, S. Karboune, R. St-Louis, S. Kermasha, Biocatal. Biotransfor., 2007, 25, 211.
  • [9] H.J. Hsieh, G.R. Nair, W.T. Wu, J. Agric. Food Chem., 2006, 54, 5777.
  • [10] Handbook of Functional Lipids, C.C. Akoh, (Red.), CRC Press (Taylor and Francis Co), Boca Raton, FL, 2005.
  • [11] Lipid Biotechnology, T.M. Kuo, H.W. Gardner, (Red.), Marcel Dekker, New York, 2002.
  • [12] Enzymes in Lipid Modification, U.T. Bornscheuer (Red.), Wiley-VCH, Weinheim, 2000.
  • [13] K.D. Mukherjee, Prog. Lipid Res., 1994, 33, 165.
  • [14] M. Cao, L.M. Fonseca, T.C. Schoenfuss, S.A. Rankin, J. Agric. Food Chem., 2014, 62, 5726.
  • [15] C.H. Okino-Delgado, L.F. Fleuri, Food Chem., 2014, 163, 103.
  • [16] F. Valero, S. Ferreira-Dias, G. Sandoval, F. Plou, Electronic J. Biotechnol., 2013, 16.
  • [17] K.-M. Park, D.E. Lee, H. Sung, J. Lee, P.-S. Chang, Food Chem., 2011, 129, 59.
  • [18] A. Rajendran, A. Palanisamy, V. Thangavelu, Braz. Arch. Biol. Technol., 2009, 52, 207.
  • [19] M. Lubary, J.H. ter Horst, G.W. Hofland, P.J. Jansens, J. Agric. Food. Chem., 2009, 57, 116.
  • [20] R. Aravindan, P. Anbumathi, T. Viruthagiri, Indian J. Biotechnol., 2007, 6, 141.
  • [21] A. Pometto, K. Shetty, G. Paliyath, R.E. Levin, Food Biotechnology, 2th ed. CRC Press (Taylor and Francis Co), Boca Raton, FL, 2005.
  • [22] V.M. Balcao, F.X. Malcata, Biotechnol. Adv., 1998, 16, 309.
  • [23] J. Wang, S. Wang, Z. Li, S. Gu, X. Wu, F. Wu, J. Mol. Catal. B: Enzym., 2015, 111, 21.
  • [24] M.-M. Zheng, L. Wang, F.-H. Huang, P.-M. Guo, F. Wei, Q.-C. Deng, C. Zheng, C.-Y. Wan, J. Mol. Catal. B: Enzym., 2013, 95, 82.
  • [25] N. Sorour, S. Karboune, R. Saint-Louis, S. Kermasha, J. Biotechnol., 2012, 158, 128.
  • [26] P. Torres, A. Poveda, J. Jimenez-Barbero, A. Ballesteros, F.J. Plou, J Agric. Food Chem., 2010, 58, 807.
  • [27] S. Karboune, R. St-Louis, S. Kermasha, J. Mol. Catal. B: Enzym., 2008, 52-53, 96.
  • [28] M. Ardhaoui, A. Falcimaigne, J.-M. Engasser, P. Moussou, G. Pauly, M. Ghoul, J. Mol. Catal. B: Enzym., 2004, 29, 63.
  • [29] V. Skouridou, E.D. Chrysina, H. Stamatis, N.G. Oikonomakos, F.N. Kolisis, J. Mol. Catal. B: Enzym., 2004, 29, 9.
  • [30] E. Enaud, C. Humeau, B. Piffaut, M. Girardin, J. Mol. Catal. B: Enzym., 2004, 27, 1.
  • [31] A. Kontogianni, V. Skouridou, V. Sereti, H. Stamatis, F.N. Kolisis, J. Mol. Catal. B: Enzym., 2003, 21, 59.
  • [32] D. Lambusta, G. Nicolosi, A. Patti, C. Sanfilippo, J. Mol. Catal. B: Enzym., 2003, 22, 271.
  • [33] H. Stamatis, V. Sereti, F.N. Kolisis, J. Mol. Catal. B: Enzym., 2001, 11, 323.
  • [34] C. Wei, X.-F. Fu, Z. Wang, X.-J. Yu, Y.-J. Zhang, J.-Y. Zheng, J. Mol. Catal. B: Enzym., 2014, 106, 90.
  • [35] P. Torres, A. Kunamneni, A. Ballesteros, F.J. Plou, The Open Food Sci. J., 2008, 2, 1.
  • [36] P. Torres, D. Reyes-Duarte, N. Lopez-Cortes, M. Ferrer, A. Ballesteros, F.J. Plou, Process Biochem., 2008, 43, 145.
  • [37] T. Maugard, B. Rejasse, M.D. Legoy, Biotechnol. Prog., 2002, 18, 424.
  • [38] T. Maugard, J. Tudella, M.D.Legoy, Biotechnol. Prog., 2000, 16, 358.
  • [39] Y. Yan, U.T. Bornscheuer, R.D. Schmid, Biotechnology Lett., 1999, 21, 1051.
  • [40] T.d.S. Fonseca, M.R.D. Silva, M.d.C.F. de Oliveira, T.L.G.d. Lemos, R.d.A. de Marques, M.C. Mattos, Appl. Catal. A: Gen., 2015, 492, 76.
  • [41] S. Sayin, E. Akoz, M. Yilmaz, Org. Biomol. Chem., 2014, 12, 6634.
  • [42] P. Borowiecki, D. Paprocki, M. Dranka, Beilstein J. Org. Chem., 2014, 10, 3038.
  • [43] J. Gonzalez-Sabin, N. Rios-Lombardia, V. Gotor, F. Moris, Tetrahedron: Asymmetry, 2013, 24, 1421.
  • [44] G.W. Huisman, S.J. Collier, Curr. Opin. Chem. Biol., 2013, 17, 284.
  • [45] T. Siodmiak, M. Ziegler-Borowska, M.P. Marszałł, J. Mol. Catal. B: Enzym., 2013, 94, 7.
  • [46] E. Busto, L. Martinez-Montero, V. Gotor, V. Gotor-Fernandez, Eur. J. Org. Chem., 2013, 2013, 4057.
  • [47] E. Busto, V. Gotor-Fernandez, V. Gotor, J. Org. Chem., 2012, 77, 4842.
  • [48] Biocatalysis in the Fine Chemical and Pharmaceutical Industries, J. Whittal, P.W. Sutton (Red.), 1st ed. John Willey & Sons, Ltd., 2012.
  • [49] J. Mangas-Sanchez, E. Busto, V. Gotor-Fernandez, F. Malpartida, V. Gotor, J. Org. Chem., 2011, 76, 2115.
  • [50] E.V. Johnston, K. Bogar, J.E. Backvall, J. Org. Chem., 2010, 75, 4596.
  • [51] K. Arunkumar, M.A. Reddy, T.S. Kumar, B.V. Kumar, K.B. Chandrasekhar, P.R. Kumar, M. Pal, Beilstein J. Org. Chem., 2010, 6, 1174.
  • [52] M. Rodriguez-Mata, E. Garcia-Urdiales, V. Gotor-Fernandez, V. Gotor, Adv. Synth. Catal., 2010, 352, 395.
  • [53] A. Ghanem, M.N. Aboul-Enein, A. El-Azzouny, M.F. El-Behairy, J. Chromatogr. A, 2010, 1217, 1063.
  • [54] J. Mangas-Sanchez, M. Rodriguez-Mata, E. Busto, V. Gotor-Fernandez, V. Gotor, J. Org. Chem., 2009, 74, 5304.
  • [55] R.N. Patel, Coordin. Chem. Rev., 2008, 252, 659.
  • [56] Biocatalysis in the Pharmaceutical and Biotechnology Industries, R.N. Patel (Red.), CRC Press Boca Raton, 2007.
  • [57] V. Gotor-Fernandez, R. Brieva, V. Gotor, J. Mol. Catal. B: Enzym., 2006, 40, 111.
  • [58] R.N. Patel, Enzyme Microb. Technol., 2002, 31, 804–826;
  • [59] R. Zhou, J.-H. Xu, Biochem. Eng. J., 2005, 23, 11.
  • [60] Y.-C. Cheng, S.-W. Tsai, Tetrahedron: Asymmetry, 2004, 15, 2917.
  • [61] K. Tanaka, K. Yoshida, C. Sasaki, Y.T. Osano, J. Org. Chem., 2002, 67, 3131.
  • [62] L.A. Spangler, M. Mikołajczyk, E.L. Burdge, P. Kiełbasiński, H.C. Smith, P. Łyzwa, J.D. Fisher, J. Omelańczuk, J. Agr. Food Chem., 1999, 47, 318.
  • [63] P.-J. Um, D.G. Drueckhammer, J. Am. Chem. Soc., 1998, 120, 5605.
  • [64] M. Inagaki, J. Hiratake, T. Nishioka, J. Oda, J. Org. Chem., 1992, 57, 5643.
  • [65] M. Inagaki, J. Hiratake, T. Nishioka, J. Oda, J. Am. Chem. Soc., 1991, 113, 9360.
  • [66] U. Takeaki, H. Hideo, Biocatalysis in Agricultural Biotechnology, American Chemical Society, str. 371; 1989.
  • [67] M.B. Ansorge-Schumacher, O. Thum, Chem. Soc. Rev., 2013, 42, 6475.
  • [68] A.B. Martins, A.M. da Silva, M.F. Schein, C. Garcia-Galan, M.A. Zachia Ayub, R. Fernandez-Lafuente, R.C. Rodrigues, J. Mol. Catal. B: Enzym., 2014, 105, 18.
  • [69] P. Lozano, J.M. Bernal, A. Navarro, Green Chem., 2012, 14, 3026.
  • [70] E. Brenna, C. Fuganti, F.G. Gatti, S. Serra, Chem. Rev., 2011, 111, 4036.
  • [71] G.A.B. Vieira, T.L.G. Lemos, M.C. de Mattos, M.d.C.F. de Oliveira, V.M.M. Melo, G. de Gonzalo, V. Gotor-Fernandez, V. Gotor, Tetrahedron: Asymmetry, 2009, 20, 214.
  • [72] E. Brenna, C. Fuganti, S. Serra, Chem. Soc. Rev., 2008, 37, 2443.
  • [73] S. Serra, C. Fuganti, E. Brenna, Trends Biotechnol., 2005, 23, 193.
  • [74] M.D. Romero, L. Calvo, C. Alba, A. Daneshfar, H.S. Ghaziaskar, Enzyme Microb. Technol. 2005, 37, 42.
  • [75] S. Serra, E. Brenna, C. Fuganti, F. Maggioni, Tetrahedron: Asymmetry, 2003, 14, 3313.
  • [76] H.O. Duşkunkorur, A. Begue, E. Pollet, V. Phalip, Y. Guvenilir, L. Averous, J. of Mol. Catal. B: Enzym., 2015, 115, 20.
  • [77] Y. Yang, J. Zhang, D. Wu, Z. Xing, Y. Zhou, W. Shi, Q. Li, Biotechnol. Adv., 2014, 32, 642.
  • [78] J. Zhang, H. Shi, D. Wu, Z. Xing, A. Zhang, Y. Yang, Q. Li, Process Biochem., 2014, 49, 797.
  • [79] C. Robert, C.M. Thomas, Chem. Soc. Rev., 2013, 42, 9392.
  • [80] Y. Yu, D. Wu, C. Liu, Z. Zhao, Y. Yang, Q. Li, Process Biochem., 2012, 47, 1027.
  • [81] Y. Yang, Y. Yu, Y. Zhang, C. Liu, W. Shi, Q. Li, Process Biochem., 2011, 46, 1900.
  • [82] S. Kobayashi, A. Makino, Chem. Rev., 2009, 109, 5288.
  • [83] C.K. Williams, Chem. Soc. Rev., 2007, 36, 1573.
  • [84] G. Rokicki, Biotechnologia, 2005, 69, 48.
  • [85] S. Kobayashi, H. Uyama, S. Kimura, Chem. Rev., 2001, 101, 3793.
  • [86] M.K.B. Weerasooriya, A.A.N. Kumarasinghe, Indian J. Chem. Techn., 2012, 19, 244.
  • [87] J.H. Jeon, J.T. Kim, Y.J. Kim, H.K. Kim, H.S. Lee, S.G. Kang, S.J. Kim, J.H. Lee, Appl. Microbiol. Biotechnol., 2009, 81, 865.
  • [88] D. Bajpai, V.K. Tyagi, J. Oleo. Sci., 2007, 56, 327.
  • [89] W.-W. Zhang, X.-L. Yang, J.-Q. Jia, N. Wang, C.-L. Hu, X.-Q. Yu, J. Mol. Catal. B: Enzym., 2015, 115, 83.
  • [90] J.K. Poppe, R. Fernandez-Lafuente, R.C. Rodrigues, M.A. Ayub, Biotechnol. Adv., 2015, In Press.
  • [91] S. Liu, K. Nie, X. Zhang, M. Wang, L. Deng, X. Ye, F. Wang, T. Tan, J. Mol. Catal. B: Enzym., 2014, 99, 43.
  • [92] A.T. Pedersen, M. Nordblad, P.M. Nielsen, J.M. Woodley, J. Mol. Catal. B: Enzym. 2014, 105, 89.
  • [93] Zhao, T. No, D.S. Kim, Y. Kim, Y.S. Kim, I.-H. J. Mol. Catal. B: Enzym., 2014, 107, 17.
  • [94] P. Yin, W. Chen, W. Liu, H. Chen, R. Qu, X. Liu, Q. Tang, Q. Xu, Bioresour. Technol., 2013, 140, 146.
  • [95] S. Yucel, P. Terzioğlu, D. Ozcimen, Lipase Applications in Biodiesel Production, Biodiesel – Feedstocks, Production and Applications, Z. Fang (Red.), InTech, 2012. DOI: 10.5772/52662.
  • [96] A.A. Mendes, R.C. Giordano, R.d.L.C. Giordano, H.F. de Castro, J. Mol. Catal. B: Enzym., 2011, 68, 109.
  • [97] D.Y.C. Leung, X. Wu, M.K.H. Leung, Appl. Energy, 2010, 87, 1083.
  • [98] T. Tan, J. Lu, K. Nie, L. Deng, F. Wang, Biotechnol. Adv., 2010, 28, 628.
  • [99] A. Bajaj, P. Lohan, P.N. Jha, R. Mehrotra, J. Mol. Catal. B: Enzym., 2010, 62, 9.
  • [100] W. Du, L. Wang, D. Liu, Green Chem. 2007, 9, 173.
  • [101] A. Salis, M. Monduzzi, V. Solinas, Industrial Enzymes, J. Polaina, A. MacCabe (Red.), Springer Netherlands, 2007, str. 317.
  • [102] H. Fukuda, A. Kondo, H. Noda, J. Biosci. Bioeng., 2001, 92, 405.
  • [103] C. Aouf, J. Lecomte, P. Villeneuve, E. Dubreucq, H. Fulcrand, Green Chem., 2012, 14, 2328.
  • [104] Z. Jiang, Biomacromolecules, 2011, 12, 1912.
  • [105] H.R. Masoumi, A. Kassim, M. Basri, D.K. Abdullah, Molecules, 2011, 16, 4672.
  • [106] S.R. Jadhav, P.K. Vemula, R. Kumar, S.R. Raghavan, G. John, Angew. Chem. Int. Ed. Engl., 2010, 49, 7695.
  • [107] G. Li, D. Yao, M. Zong, Eur. Polym. J., 2008, 44, 1123.
  • [108] M.C. Franssen, P. Steunenberg, E.L. Scott, H. Zuilhof, J.P. Sanders, Chem. Soc. Rev., 2013, 42, 6491.
  • [109] P. Bajpai, Biotechnol. Progr., 1999, 15, 147.
  • [110] S. Fukuda, S. Hayashi, H. Ochiai, T. Iiizumi, K. Nakamura, Improvers for deinking of wastepaper, 1990, JP 2229290.
  • [111] P. Saranya, K. Ramani, G. Sekaran, RSC Adv., 2014, 4, 10680.
  • [112] R. Margesin, D. Labbe, F. Schinner, C.W. Greer, L.G. Whyte, Appl. Environ. Microbiol., 2003, 69, 3085.
  • [113] R. Margesin, G. Zimmerbauer, F. Schinner, Biotechnol. Tech., 1999, 13, 313.
  • [114] L. Mita, V. Sica, M. Guida, C. Nicolucci, T. Grimaldi, L. Caputo, M. Bianco, S. Rossi, U. Bencivenga, M.S.M. Eldin, M.A. Tufano, D.G. Mita, N. Diano, J. Mol. Catal. B: Enzym., 2010, 62, 133.
  • [115] P.J. Halling, H.L. Holland, Enzymes in Nonaqueous Solvents: Methods and Protocols, E.N. Vulfson (Red.), Humana Press: Totowa, NJ. 2001.
  • [116] Z.-F. Xie, Tetrahedron: Asymmetry, 1991, 2, 733.
  • [117] K.K. Kim, H.K. Song, D.H. Shin, K.Y. Hwang, S. Choe, O.J. Yoo, S.W. Suh, Structure 1997, 5, 1571.
  • [118] http://www.uniprot.org/uniprot/?query=yourlist:M201501202EOV51B2KV&sort=yourlist:M201501202EOV51B2KV&columns=yourlist%28M201501202EOV51B2KV%29,id,entry%20name,reviewed,protein%20names,genes,organism,length
  • [119] http://srs.ebi.ac.uk/
  • [120] C. Angkawidjaja, D.J. You, H. Matsumura, K. Kuwahara, Y. Koga, K. Takano, S. Kanaya, FEBS Lett., 2007, 581, 5060.
  • [121] R.A. MacKeith, R. McCague, H.F. Olivo, S.M. Roberts, S.J.C. Taylor, H. Xiong, Bioorg. Med. Chem., 1994, 2, 387.
  • [122] R.A. MacKeith, R. McCague, H.F. Olivo, C.F. Palmer, S.M. Roberts, J. Chem. Soc., Perkin Trans. 1, 1993, 313.
  • [123] S.J.C. Taylor, R. McCague, Resolution of a versatile hydroxylactone synthon 4-endohydroxy-2-oxabicyclo[3.3.0]oct-7-en-3-one by lipase deesterification, [w:] Chirality In Industry II, A.N. Collins, G.N. Sheldrake, J. Crosby (Red.), John Wiley & Sons, New York 1997, str. 190.
  • [124] J.M. Guisan Seijas, P. Armisen Gil, P. Sabuquillo Castrillo, G. Fernandez-Lorente, R. Fernandez--Lafuente, A. Bastida Codina, J. Huguet Clotet, A. Bosch Rovira, E. de Ramon Amat, Enzymatic process for obtaining enantiomerically pure ethyl (R)-2-hydroxy-4-phenylbutanoate using immobilized-lipase biocatalysts, 2000, Span ES2145702.
  • [125] M. Journet, R.D. Larsen, S.T. Sarraf, A. Shafiee, M.D. Truppo, V. Upadhyay, Enzymatic preparation of chiral indole esters, 2004, WO 2004104205.
  • [126] M.D. Truppo, M. Journet, A. Shafiee, J.C. Moore, Org. Proc. Res. Dev., 2006, 10, 592.
  • [127] P. Dominguez de Maria, J.M. Sanchez-Montero, J.V. Sinisterra, A.R. Alcantara, Biotechnol. Adv., 2006, 24, 180.
  • [128] J.M. Mancheno, M.A. Pernas, M.J. Martinez, B. Ochoa, M.L. Rua, J.A. Hermoso, J. Mol. Biol., 2003, 332, 1059.
  • [129] P. Grochulski, Y. Li, J.D. Schrag, M. Cygler, Protein Sci., 1994, 3, 82.
  • [130] D. Herbst, S. Peper, J.F. Fernandez, W. Ruck, B. Niemeyer, J. Mol. Catal. B: Enzym., 2014, 100, 104.
  • [131] F. Kartal, M.H.A. Janssen, F. Hollmann, R.A. Sheldon, A. Kilinc, J. Mol. Catal. B: Enzym., 2011, 71, 85.
  • [132] G. Ozyilmaz, E. Gezer, J. Mol. Catal. B: Enzym., 2010, 64, 140.
  • [133] T. Raghavendra, D. Sayania, D. Madamwar, J. Mol. Catal. B: Enzym., 2010, 63, 31.
  • [134] A. Padney, S. Benjamin, C.R. Soccol, P. Nigam, N. Krieger, V.T. Soccol, Biotechnol. Appl. Biochem., 1999, 29, 119.
  • [135] C. Tsitsimpikou, H. Daflos, F.N. Kolisis, J. Mol. Catal. B: Enzym., 1997, 3, 189.
  • [136] J. Schmitt, S. Brocca, R.D. Schmid, J. Pleiss, Protein. Eng., 2002, 15, 595.
  • [137] R.A. Sheldon, Chirotechnology, Marcel Dekker Inc., New York, 1993.
  • [138] F.X. McConville, J.L. Lopez, S.A. Wald, Enzymatic resolution of ibuprofen in a multiphase membrane reactor, [w:] Biocatalysis, D.A. Abramowicz (Red.), van Nostrand Reinhold, New York 1990, str. 167.
  • [139] C.J. Sih, Process for preparing (S)-α-methylarylacetic acids, 1987, EP 0227078.
  • [140] J.M. Guisan Seijas, P. Armisen Gil, P. Sabuquillo Castrillo, G. Fernandez Lorente, R. Fernandez--Lafuente, A. Bastida Codina, J. Huguet Clotet, A. Bosch Rovira, E. de Ramon Amat, Immobilized lipase biocatalysts, 1999, PCT Int. Appl., WO9951726.
  • [141] S.r.V. Lehmann, J. Breinholt, P.S. Bury, T.E. Nielsen, Chirality, 2000, 12, 568.
  • [142] S. Santini, J.M Crowet, A. Thomas, M. Paquot, M. Vandenbol, P. Thonart, J. P. Wathelet, C. Blecker, G. Lognay, R. Brasseur, L. Lins, B. Charloteaux, Biophys. J., 2009, 96, 4814.
  • [143] R. Fernandez-Lafuente, J. Mol. Catal. B: Enzym., 2010, 62, 197.
  • [144] W. Bonrath, D. Eisenkratzer, V. Enjolras, R. Karge, T. Netscher, M. Schneider, Process for the manufacture of a vitamin E intermediate, 2002, European patent EP 1239045.
  • [145] W. Bonrath, R. Karge, T. Netscher, J. Mol. Catal. B: Enzym., 2002, 19-20, 67.
  • [146] C.A. Martinez, S. Hu, Y. Dumond, J. Tao, P. Kelleher, L. Tully, Org. Process Res. Dev., 2008, 12, 392.
  • [147] X.Y. Wu, S. Jaaskelainen, Y.-Y. Linko, Appl. Biochem. Biotechnol., 1996, 59, 145.
  • [148] L. Brady, A.M. Brzozowski, Z.S. Derewenda, E. Dodson, G. Dodson, S. Tolley, J.P. Turkenburg, L. Christiansen, B. Huge-Jensen, L. Norskov, L. Thim, U. Menge, Nature, 1990, 343, 767.
  • [149] Z.S. Derewenda, U. Derewenda, G.G. Dodson, J. Mol. Biol., 1992, 227, 818.
  • [150] A.M. Brzozowski, Z.S. Derewenda, E.J. Dodson, G.G. Dodson, J.P. Turkenburg, Acta Crystallogr. B Struct. Sci., 1992, 48, 307.
  • [151] U. Derewenda, A.M. Brzozowski, D.M. Lawson, Z.S. Derewenda, Biochemistry, 1992, 31, 1532.
  • [152] G.J. Moskowitz, R. Cassaigne, I.R. West, T. Shen, L.I. Feldman, J. Agric. Food Chem., 1977, 25, 1146.
  • [153] R.C. Rodrigues, R. Fernandez-Lafuente, J. Mol. Catal. B: Enzym., 2010, 66, 15.
  • [154] R.C. Rodrigues, R. Fernandez-Lafuente, J. Mol. Catal. B: Enzym., 2010, 64, 1.
  • [155] N. Turner, J. Winterman, R. McCague, A method for preparing tert-leucine and analogues thereof in enantiomeric form, and intermediates therein, 1995, PCT Int Appl WO9512573.
  • [156] J.A. Blacker, D. Schofield, Esters of (R) 2-(2-hydroxybutyl)-3-chlorothiophene and a process for the resolution of (S) 2-(2-hydroxybutyl)-3-chlorothiophene, 1996 Brit UK Pat Appl GB2299332.
  • [157] J.M. Guisan Seijas, G. Fernandez-Lorente, R. Fernandez-Lafuente, C. Mateo Gonzalez, C. Ceinos Rodriguez, P. Dalmases Barjoan, E. de Ramon Amat, Enzymatic hydrolysis for paroxetine synthesis intermediates production consists of enantioselective hydrolysis of a racemic ester based mixture, 2001, Span ES2161167.
  • [158] J.M. Palomo, R.L. Segura, C. Mateo, M. Terreni, J.M. Guisan, R. Fernandez-Lafuente, Tetrahedron: Asymmetry, 2005, 16, 869.
  • [159] V.H.M. Elferink, Progress in the application of biocatalysis in the industrial scale manufacture of chiral molecules, Chiral USA 96, 11th International Spring Innovations Chirality Symposium, 1995, str. 79, Boston.
  • [160] W.E. Ladner, G.M. Whitesides, J. Am. Chem. Soc., 1984, 106, 7250.
  • [161] F. Balkenhohl, K. Ditrich, B. Hauer, W. Ladner, Journal fur Praktische Chemie/Chemiker-Zeitung, 1997, 339, 381.
  • [162] F. Balkenhohl, B. Hauer, W. Ladner, U. Schnell, U. Pressler, H.R. Staudenmaier, Lipase katalysierte Acylierung von Alkoholen mit Diketenen, (1995), BASF AG, DE 4329293 A1.
  • [163] T. Shibatani, K. Omori, H. Akatsuka, E. Kawai, H. Matsumae, J. Mol. Catal. B Enzym., 2000, 10, 141.
  • [164] R.A. Sheldon, J. Chem. Tech. Biotechnol., 1996, 67, 1.
  • [165] T. Remarchuk, F. St-Jean, D. Carrera, S. Savage, H. Yajima, B. Wong, S. Babu, A. Deese, J. Stults, M.W. Dong, D. Askin, J.W. Lane, K.L. Spencer, Org. Proc. Res. Dev., 2014, 18, 1652.
  • [166] R.J. Kazlauskas, A.N.E. Weissfloch, A.T. Rappaport, L.A. Cuccia, J. Org. Chem., 1991, 56, 2656.
  • [167] Z. Guan, L.-Y. Li, Y.-H. He, RSC Adv., 2015, 5, 16801.
  • [168] M. Kapoor, M.N. Gupta, Process Biochem., 2012, 47, 555.
  • [169] M.S. Humble, P. Berglund, Eur. J. Org. Chem., 2011, 2011, 3391.
  • [170] E. Busto, V. Gotor-Fernandez, Gotor, V. Chem. Soc. Rev., 2010, 39, 4504.
  • [171] U.T. Bornscheuer, R.J. Kazlauskas, Angew. Chem. Int. Ed. Engl., 2004, 43, 6032.
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