The design and development of greener processes that are safe and friendly is an irreversible trend that is driven by sustainable and economic issues. The use of Biocatalysis as part of a manufacturing process fits well in this trend as enzymes are themselves biodegradable, require mild conditions to work and are highly specific and well suited to carry out complex reactions in a simple way. The growth of computational capabilities in the last decades has allowed Biocatalysis to develop sophisticated tools to understand better enzymatic phenomena and to have the power to control not only process conditions but also the enzyme’s own nature. Nowadays, Biocatalysis is behind some important products in the pharmaceutical, cosmetic, food and bulk chemicals industry. In this review we want to present some of the most representative examples of industrial chemicals produced in vitro through enzymatic catalysis.
References
[1]
Council of European Union. En Route to the Knowledge-Based Bio-Economy; German Presidency of the Council of European Union: Cologne, Germany, 2007.
[2]
Sandoval, G.; Plou, F.G. Obtención enzimática de compuestos bioactivos a partir de recursos naturales iberoamericanos; Consejo Superior de Instigaciones Cientificas (CSIC): Madrid, Spain, 2012; pp. 1–336.
[3]
Jahnz, U.; Schubert, M.; Baars, H.; Klaus, V. Process for producing the potential food ingredient DFA III from inulin-screening, genetic engineering, fermentation and immobilisation of inulase II. Int. J. Pharm. 2003, 256, 199–206, doi:10.1016/S0378-5173(03)00078-4.
[4]
Uchiyama, T.; Niwa, S.; Tanaka, K. Purification and properties of Arthrobacter ureafaciens inulase II. Biochim. Biophys. Acta 1973, 315, 412–420, doi:10.1016/0005-2744(73)90271-4.
[5]
Kim, G.E.; Lee, S. Efficient production of DFA III (di-d-fructofuranose-dianhydride) from chicory root. In Abstracts of the World Congress on Biotechnology; DECHEMA: Berlin, Germany, 2000; Volume 272.
[6]
Yokota, A.; Hirayama, S.; Enomoto, K.; Miura, Y.; Takao, S.; Tomita, F. Production of inulin fructotransferase (depolymerizing) by Arthrobacter sp. H65–7 and preparation of DFA III from inulin by the enzyme. J. Ferm. Bioeng 1991, 72, 258–261, doi:10.1016/0922-338X(91)90159-E.
[7]
Kawamura, M.; Takahashi, S.; Uchiyama, T. Purification and some properties of inulin fructotransferase (depolymerizing) from Arthrobacter ilicis. Agric. Biol. Chem. 1988, 52, 3209–3210.
Rastall, R.A.; Gibson, G.R.; Gill, H.S.; Guarner, F.; Klaenhammer, T.R.; Pot, B.; Reid, G.; Rowland, I.R.; Sanders, M.E. Modulation of the microbial ecology of the human colon by probiotics, prebiotics and synbiotics to enhance human health: An overview of enabling science and potential applications. FEMS Microbiol. Ecol. 2005, 52, 145–152, doi:10.1016/j.femsec.2005.01.003.
[10]
Sanz, J.I. Production of Glactooligo-Sacchariddes from Lactose by Immobilized β-Galactosidase and Posterioir Chromatographic Spearation. Ph.D. Thesis, Ohio State University, Columbus, OH, USA, 2009.
Neri, D.F.M.; Balca？o, V.M.; Costa, R.S.; Rocha, I.C.A.P.; Ferreira, E.M.F.C.; Torres, D.P.M.; Rodrigues, L.R.M.; Carvalho, L.B., Jr.; Teixeira, J.A. Galacto-oligosaccharides production during lactose hydrolysis by free Aspergillus oryzae β-galactosidase and immobilized on magnetic polysiloxane-polyvinyl alcohol. Food Chem. 2009, 115, 92–99, doi:10.1016/j.foodchem.2008.11.068.
[13]
Barreteau, H.; Delattre, C.; Michaud, P. Production of oligosaccharides as promising new food additive generation. Food Technol. Biotechnol. 2006, 44, 323–333.
Whisner, C.M.; Weaver, C.M. Galacto-oligosaccharides: Prebiotic effects on calcium absorption and bone health. In Nutritional Influences on Bone Health; Burckhardt, P., Dawson-Hughes, B., Weaver, C.M., Eds.; Springer: London, UK, 2013; pp. 315–323.
[16]
Perugino, G.; Trincone, A.; Rossi, M.; Moracci, M. Oligosaccharide synthesis by glycosynthases. Trends Biotech. 2004, 22, 31–37, doi:10.1016/j.tibtech.2003.10.008.
Rodríguez, B.; Poveda, A.; Jiménez, J.; Ballesteros, A.O.; Plou, F.J. Galacto-oligosaccharide synthesis from lactose solution or skim milk using the β-galactosidase from Bacillus circulans. J. Agric. Food Chem. 2012, 60, 6391–6398.
[19]
Torres, D.; Gon？alves, M.D.P.F.; Teixeira, J.A.; Rodrigues, L. Galacto-oligosaccharides: Production, properties, applications, and significance as prebiotics. Compr. Rev. Food Sci. F. 2010, 9, 438–454, doi:10.1111/j.1541-4337.2010.00119.x.
[20]
Tzortzis, G.; Vulevic, J. Galacto-oligosaccharide prebiotics. In Prebiotics and Probiotics Science and Technology; Charalampopoulos, D., Rastall, R.A., Eds.; Springer: New York, NY, USA, 2009; pp. 207–244.
[21]
Park, H.Y.; Kim, H.J.; Lee, J.K.; Kim, D.; Oh, D.K. Galactooligosaccharide production by a thermostable β-galactosidase from Sulfolobus solfataricus. World J. Microb. Biot. 2008, 24, 1553–1558, doi:10.1007/s11274-007-9642-x.
[22]
Rodriguez, B.; de Abreu, M.A.; Fernandez, L.; de Beer, R.; Poveda, A.; Jimenez, J.; Haltrich, D.; Ballesteros, A.O.; Fernandez, M.; Plou, F.J. Production of galacto-oligosaccharides by the β-galactosidase from Kluyveromyces lactis: Comparative analysis of permeabilized cells versus soluble enzyme. J. Agric. Food Chem. 2011, 59, 10477–10484, doi:10.1021/jf2022012.
[23]
Hsu, C.A.; Lee, S.L.; Chou, C.C. Enzymatic production of galactooligosaccharides by β-galactosidase from Bifidobacterium longum BCRC 15708. J. Agric. Food Chem. 2007, 55, 2225–2230, doi:10.1021/jf063126+.
[24]
Hansson, T.; Adlercreutz, P. Optimization of galactooligosaccharide production from lactose using β-glycosidases from hyperthermophiles. Food Biotechnol. 2001, 15, 79–97.
[25]
UBIC Europe Marketing Consulting. In The World GOS Market; UBIC Europe Press: Sierre, Switzerland, 2010.
[26]
Padalino, M.; Perez-Conesa, D.; Lo？pez-Nicola？s, R.; Frontela-Saseta, C.; Berruezo, G. Effect of fructooligosaccharides and galactooligosaccharides on the folate production of some folate-producing bacteria in media cultures or milk. Int. Dairy J. 2012, 27, 27–33, doi:10.1016/j.idairyj.2012.06.006.
[27]
Fanaro, S.; Boehm, G.; Garssen, J.; Knol, J.; Mosca, F.; Stahl, B.; Vigi, V. Galacto-oligosaccharides and long-chain fructo-oligosaccharides as prebiotics in infant formulas: A review. Acta Paediatr. Suppl. 2005, 94, 22–26, doi:10.1080/08035320510043538.
[28]
Watzl, B.; Girrbach, S.; Roller, M. Inulin, oligofructose and immunomodulation. Br. J. Nutr. 2005, 93, S49–S55, doi:10.1079/BJN20041357.
[29]
Bornet, F.R.; Brouns, F.; Tashiro, Y.; Duvillier, V. Nutritional aspects of short-chain fructooligosaccharides: Natural occurrence, chemistry, physiology and health implications. Dig. Liver Dis. 2002, 34, S111–S120, doi:10.1016/S1590-8658(02)80177-3.
Arrizon, J.; Urias-Silvas, J.E.; Sandoval, G.; Mancilla-Margalli, N.A.; Gschaedler, A.C.; Morel, S.; Monsan, P. Production and bioactivity of fructan-type oligosaccharides. In Food Oligosaccharides: Production, Analysis and Bioactivity; Moreno, F.J., Sanz, M.L., Eds.; Wiley-Blackwell: Hoboken, NJ, USA, 2013. in press.
[32]
Beine, R.; Morarua, R.; Nimtz, M.; Na’amniehc, S.; Pawlowskic, A.; Buchholz, K.; Seibel, J. Synthesis of novel fructooligosaccharides by substrate and enzyme engineering. J. Biotechnol. 2008, 138, 33–41, doi:10.1016/j.jbiotec.2008.07.1998.
[33]
Castillo, E.; Lo？pez-Munguía, A. Synthesis of levan in water-miscible organic solvents. J. Biotechnol. 2004, 114, 209–217, doi:10.1016/j.jbiotec.2004.06.003.
[34]
Vega, R.J.; Zu？niga, M.E. Potential application of commercial enzyme preparations for industrial production of short-chain fructooligosaccharides. J. Mol. Catal. B Enzym. 2012, 76, 44–51, doi:10.1016/j.molcatb.2011.12.007.
[35]
Singh, R.S.; Singh, R.P. Production of fructooligosaccharides from inulin by endoinulinases and their prebiotic potential. Food Technol. Biotech. 2010, 48, 435–450.
[36]
Tanriseven, A.; Aslan, Y. Immobilization of Pectinex Ultra SP-L to produce fructooligosaccharides. Enzyme Microb. Technol. 2005, 36, 550–554, doi:10.1016/j.enzmictec.2004.12.001.
Jala, R.C.R.; Hu, P.; Yang, T.; Jiang, Y.; Zheng, Y; Xu, X. Lipases as biocatalysts for the synthesis of structured lipids. In Lipases and Phospholipases. Methods in Molecular Biology; Sandoval, G., Ed.; Springer-Humana Press: New York, USA, 2012; Volume 861. Chapter 23.
[39]
Xu, X.; Akoh, C.C. Enzymatic production of Betapol and other specialty fats. In Lipid Biotechnology; Marcel Dekker: New York, NY, USA, 2002; pp. 461–478.
[40]
Odle, J. New insights into the utilization of medium-chain triglycerides by the neonate: Observations from a piglet model. J. Nutr. 1997, 127, 1061–1067.
[41]
Bugaut, M. Occurrence, absorption and metabolism of short chain fatty acids in the digestive tract of mammals. Comp. Biochem. Physiol. B Biochem. Mol. Biol. 1987, 86, 439–472.
[42]
Osborn, H.T.; Akoh, C. Structured lipids: Novel fats with medical, nutraceutical, and food applications. Compr. Rev. Food Sci. F. 2002, 1, 110–120, doi:10.1111/j.1541-4337.2002.tb00010.x.
[43]
Xu, X.; Hoy, C.E.; Balchen, S.; Adler-Nissen, J. Specific-Structured Lipid: Nutritional Perspectives and Production Potentials. In Proceedings of International Symposium on the Approach to Functional Cereals and Oils, CCOA, Beijing, China, 9–14 November 1997.
[44]
Trivedi, R.; Singh, R.P. Modification of oils and fats to produce structured lipids. J. Oleo Sci. 2005, 54, 423–430, doi:10.5650/jos.54.423.
[45]
Hellner, G.; T？ke, E.R.; Nagy, V.; Szaka？cs, G.; Poppe, L. Integrated enzymatic production of specific structured lipid and phytosterol ester compositions. Process Biochem. 2010, 45, 1245–1250, doi:10.1016/j.procbio.2010.04.008.
[46]
Lee, K.T.; Akoh, C.C. Characterization of enzymatically synthesized structured lipids containing eicosapentaenoic, docosahexaenoic, and caprylic acids. J. Am. Oil Chem. Soc. 1998, 75, 495–499, doi:10.1007/s11746-998-0253-y.
[47]
Akoh, C.C. Structured lipids. In Food Lipids Chemistry, Nutrition, and Biotechnology; Akoh, C.C., Min, D.B., Eds.; Marcel Dekker: New York, NY, USA, 1998; pp. 699–727.
[48]
Iwasaki, Y.; Yamane, T. Enzymatic synthesis of structured lipids. J. Mol. Catal. B Enzym. 2000, 10, 129–140, doi:10.1016/S1381-1177(00)00120-X.
[49]
Khodadadi, M.; Aziz, S.; St-Louis, R.; Kermash, S. Lipase-catalyzed synthesis and characterization of flaxseed oil-based structured lipids. J. Funct. Foods 2013, 5, 424–433, doi:10.1016/j.jff.2012.11.015.
[50]
Casas-Godoy, L.; Marty, A.; Sandoval, G.; Ferreira-Dias, S. Optimization of medium chain length fatty acid incorporation into olive oil catalyzed by immobilized Lip2 from Yarrowia lipolytica. Biochem. Eng. J. 2013, 77, 20–27, doi:10.1016/j.bej.2013.05.001.
[51]
Villeneuve, P.; Barouh, N.; Baréa, B.; Piombo, G.; Figueroa-Espinoza, M.C.; Turon, M.C.; Pina, M.; Lago, R. Chemoenzymatic synthesis of structured triacylglycerols with conjugated linoleic acids (CLA) in central position. Food Chem. 2007, 100, 1443–1452, doi:10.1016/j.foodchem.2005.12.018.
[52]
Nagachinta, S.; Akoh, C.C. Enrichment of palm olein with long chain polyunsaturated fatty acids by enzymatic acidolysis. LWT Food Sci. Technol. 2012, 46, 29–35, doi:10.1016/j.lwt.2011.10.027.
[53]
Tecel？o, C.; Rivera, I.; Sandoval, G.; Ferreira-Dias, S. Carica papaya latex: A low-cost biocatalyst for human milk fat substitutes production. Eur. J. Lipid Sci. Technol. 2012, 114, 266–276, doi:10.1002/ejlt.201100226.
[54]
Nagao, T.; Watanabe, Y.; Maruyama, M.; Momokawa, Y.; Kishimoto, N.; Shimada, Y. One-pot enzymatic synthesis of docosahexaenoic acid-rich triacylglycerols at the sn-1(3) position using by-product from selective hydrolysis of tuna oil. New Biotechnol. 2011, 28, 7–13.
[55]
Buchholtz, K.; Volker, K.; Borscheuer, U.T. Biocatalysts and Enzyme Technology; Wiley-VCH: Berlin, Germany, 2005; pp. 1–465.
[56]
Bornscheuer, U.T.; Kazlauskas, R.J. Hydrolases in Organic Synthesis—Regio- and Stereoselective Biotransformations; Wiley-VCH: Berlin, Germany, 1999; pp. 1–355.
[57]
Cao, L. Carrier-Bound Immobilized Enzymes; Wiley-VCH: Berlin, Germany, 2005; pp. 1–578.
[58]
Gog, A.; Roman, M.; To？a, M.; Paizs, C.; Irimie, F.D. Biodiesel production using enzymatic transesterification—Current state and perspectives. Renew. Energ. 2012, 39, 10–16, doi:10.1016/j.renene.2011.08.007.
[59]
Ve？ras, I.C.; Silva, F.A.; Ferra？o-Gonzales, A.D.; Moreau, V.H. One-step enzymatic production of fatty acid ethyl ester from high-acidity waste feedstocks in solvent-free media. Bioresour. Technol. 2011, 102, 9653–9658, doi:10.1016/j.biortech.2011.08.012.
[60]
Fan, X.; Niehus, X.; Sandoval, G. Lipases as biocatalyst for biodiesel production. In Lipases and Phospholipases. Methods in Molecular Biology; Sandoval, G., Ed.; Springer-Humana Press: New York, NY, USA, 2012; Volume 861. Chapter 27.
[61]
Fukuda, H.; Kondo, A.; Noda, H. Biodiesel fuel production by transesterification of oils. J. Biosci. Bioeng. 2001, 92, 405–416.
[62]
Maleki, E.; Aroua, M.K.; Sulaiman, N.M.N. Improved yield of solvent free enzymatic methanolysis of palm and jatropha oils blended with castor oil. Appl. Energ. 2013, 104, 905–909, doi:10.1016/j.apenergy.2012.12.009.
[63]
Hama, S.; Kondo, A. Enzymatic biodiesel production: An overview of potential feedstocks and process development. Bioresour. Technol. 2013, 135, 386–395, doi:10.1016/j.biortech.2012.08.014.
[64]
Al-Zuhair, S.; Hasan, M.; Ramachandran, K.B. Kinetics of the enzymatic hydrolysis of palm oil by lipase. Process Biochem. 2003, 38, 1155–1163.
[65]
Salis, A.; Pinna, M.; Monduzzi, M.; Solinas, V. Biodiesel production from triolein and short chain alcohols through biocatalysis. J. Biotechnol. 2005, 119, 291–299.
[66]
Shimada, Y.; Watanabe, Y.; Samukawa, T.; Sugihara, A.; Noda, H.; Fukuda, H.; Tominaga, Y. Conversion of vegetable oil to biodiesel using immobilized Candida antarctica lipase. J. Am. Oil Chem. Soc. 1999, 76, 789–793.
[67]
Li, Q.; Xu, J.; Du, W.; Li, Y.; Liu, D. Ethanol as the acyl acceptor for biodiesel production. Renew. Sust. Energ. Rev. 2013, 25, 742–748.
[68]
Modi, M.K.; Reddy, J.R.; Rao, B.V.; Prasad, R.B. Lipase mediated conversion of vegetable oils into biodiesel using ethyl acetate as acyl acceptor. Bioresour. Technol. 2007, 98, 1260–1264.
[69]
Rivera, I.; Villanueva, G.; Sandoval, G. Biodiesel production from animal grease wastes by enzymatic catalysis. Grasas Aceites 2009, 60, 468–474.
[70]
Royon, D.; Daz, M.; Ellenrieder, G.; Locatelli, S. Enzymatic production of biodiesel from cotton seed oil using t-butanol as a solvent. Bioresour. Technol. 2007, 98, 648–653.
[71]
Abigor, R.D.; Uadia, P.O.; Foglia, T.A.; Haas, M.J.; Jones, K.C.; Okpefa, E.; Obibuzor, J.U.; Bafor, M.E. Lipase-catalysed production of biodiesel fuel from some Nigerian lauric oils. Biochem. Soc. Trans. 2000, 28, 979–981.
[72]
Nelson, L.; Foglia, T.; Marmer, W.N. Lipase-catalyzed production of biodiesel. J. Am. Oil Chem. Soc. 1996, 73, 1191–1195, doi:10.1007/BF02523383.
[73]
Linko, Y.Y.; Lams？, M.; Huhtala, A.; Rantanen, O. Lipase biocatalysis in the production of esters. J. Am. Oil Chem. Soc. 1995, 72, 1293–1299.
[74]
Du, W.; Xu, Y.; Liu, D.; Zeng, J. Comparative study on lipase-catalyzed transformation of soybean oil for biodiesel production with different acyl acceptors. J. Mol. Catal. B Enzym. 2004, 30, 125–129, doi:10.1016/j.molcatb.2004.04.004.
[75]
Watanabe, Y.; Shimada, Y.; Sugihara, A.; Noda, H.; Fukuda, H.; Tominaga, Y. Continuous production of biodiesel fuel from vegetable oil using immobilized Candida antarctica lipase. J.Am. Oil Chem. Soc. 2000, 77, 355–360.
[76]
Zhang, B.; Weng, Y.; Xu, H.; Mao, Z. Enzyme immobilization for biodiesel production. Appl. Microbiol. Biotechnol. 2012, 93, 61–70, doi:10.1007/s00253-011-3672-x.
[77]
Soumanou, M.M.; Bornscheuer, U.T. Lipase-catalyzed alcoholysis of vegetable oils. Eur. J. Lipid Sci. Technol. 2003, 105, 656–660.
[78]
Zhu, X.; Zhou, T.; Wu, X.; Cai, Y.; Yao, D.; Xie, C.; Liu, D. Covalent immobilization of enzymes within micro-aqueous organic media. J. Mol. Catal. B Enzym 2011, 3–4, 145–149.
[79]
Zaks, A.; Klibanov, A.M. Enzyme-catalyzed processes in organic solvents. Proc. Natl. Acad. Sci. USA 1985, 82, 3192–3196, doi:10.1073/pnas.82.10.3192.
[80]
Iso, M.; Chen, B.; Eguchi, M.; Kudo, T.; Shrestha, S. Production of biodiesel fuel from triglycerides and alcohol using immobilized lipase. J. Mol. Catal. B Enzym. 2001, 16, 53–58, doi:10.1016/S1381-1177(01)00045-5.
[81]
Chen, J.W.; Wu, W.T. Regeneration of immobilized Candida antarctica lipase for transesterification. J. Biosci. Bioeng. 2003, 95, 466–469.
[82]
Nie, K.; Xie, F.; Wang, F.; Tan, T. Lipase catalyzed methanolysis to produce biodiesel: optimization of the biodiesel production. J. Mol. Catal. B Enzym. 2006, 43, 142–147, doi:10.1016/j.molcatb.2006.07.016.
[83]
Ciftci, O.N.; Temelli, F. Enzymatic conversion of corn oil into biodiesel in a batch supercritical carbon dioxide reactor and kinetic modeling. J. Supercrit. Fluids. 2013, 75, 172–180, doi:10.1016/j.supflu.2012.12.029.
[84]
Lin, Y.C.; Yang, P.M.; Chen, S.C.; Lin, J.F. Improving biodiesel yields from waste cooking oil using ionic liquids as catalysts with a microwave heating system. Fuel Process. Technol. 2013, 115, 57–62, doi:10.1016/j.fuproc.2013.04.004.
[85]
Earle, M.J.; Plechkova, N.V.; Seddon, K.R. Green synthesis of biodiesel using ionic liquids. Pure Appl. Chem. 2009, 81, 2045–2057.
[86]
Ha, S.H.; Lan, M.N.; Lee, S.H.; Hwang, S.M.; Koo, Y.M. Lipase-catalyzed biodiesel production from soybean oil in ionic liquids. Enzyme Microb. Technol. 2007, 41, 480–483.
[87]
Koda, R.; Numata, T.; Hama, S.; Tamalampudi, S.; Nakashima, K.; Tanaka, T; Ogino, C.; Fukuda, H.; Kondo, A. Ethanolysis of rapeseed oil to produce biodiesel fuel catalyzed by Fusarium heterosporum lipase-expressing fungus immobilized whole-cell biocatalysts. J. Mol. Catal. B Enzym. 2010, 68, 101–104.
[88]
Adachi, D.; Koha, F.; Hamab, S.; Ogino, C.; Kondo, A. A robust whole-cell biocatalyst that introduces a thermo- and solvent-tolerant lipase into Aspergillus oryzae cells: Characterization and application to enzymatic biodiesel production. Enzyme Microb. Technol. 2013, 52, 331–335, doi:10.1016/j.enzmictec.2013.03.005.
[89]
Fukuda, H.; Hama, S.; Tamalampudi, S.; Noda, H. Whole-cell biocatalysts for biodiesel fuel production. Trends Biotechnol. 2008, 26, 668–673, doi:10.1016/j.tibtech.2008.08.001.
[90]
Atkinson, B.; Black, G.M.; Lewis, P.J.S.; Pinches, A. Biological particles of given size, shape, and density for use in biological reactors. Biotechnol. Bioeng. 1979, 21, 193–200.
[91]
Meng, X.; Yang, J.; Xu, X.; Zhang, L.; Nie, Q.; Xian, M. Biodiesel production from oleaginous microorganisms. Renew. Energ. 2009, 34, 1–5, doi:10.1016/j.renene.2008.04.014.
[92]
Turner, N.J.; Truppo, M.D. Biocatalysis enters a new era. Curr. Opin. Chem. Biol. 2013, 17, 212–214, doi:10.1016/j.cbpa.2013.02.026.
[93]
Woodley, J. New opportunities for biocatalysis: Making pharmaceutical processes greener. Trends Biotechnol. 2008, 26, 321–327, doi:10.1016/j.tibtech.2008.03.004.
[94]
Kittl, R.; Withers, S.G. New approaches to enzymatic glycoside synthesis through directed evolution. Carbohyd. Res. 2010, 345, 1272–1279, doi:10.1016/j.carres.2010.04.002.
[95]
Hay, A.S. Polymerization by oxidative coupling: Discovery and commercialization of PPO？. J. Polym. Sci. Pol. Chem. 1998, 36, 505–517, doi:10.1002/(SICI)1099-0518(199803)36:4<505::AID-POLA1>3.0.CO;2-O.
[96]
He, F.; Li, S.; Garreau, H.; Vert, M.; Zhuo, R. Enzyme-catalyzed polymerization and degradation of copolyesters of ε-caprolactone and γ-butyrolactone. Polymer 2005, 46, 12682–12688, doi:10.1016/j.polymer.2005.10.121.
[97]
Salvachúa, D.; Prieto, A.; Mattinen, M.L.; Tamminen, T.; Liiti？, T.; Lille, M.; Willf？r, S.; Martínez, A.T.; Martínez, M.J.; Faulds, C.B. Versatile peroxidase as a valuable tool for generating new biomolecules by homogeneous and heterogeneous cross-linking. Enzyme Microb. Technol. 2013, 52, 303–311, doi:10.1016/j.enzmictec.2013.03.010.
Mita, N.; Oguchi, T.; Tawaki, S.; Uyama, H.; Kobayashi, S. Control of structure and molecular weight of polyphenols in enzymatic oxidative polymerization. Polymer Prepr. 2000, 41, 223–224.
[102]
Kurioka, H.; Komatsu, I.; Uyama, H.; Kobayashi, S. Enzymatic oxidative polymerization of alkylphenols. Macromol. Rapid Commun. 1994, 15, 507–510, doi:10.1002/marc.1994.030150609.
[103]
Uyama, H.; Kurioka, H.; Kobayashi, S. Preparation of polyphenol particles by dispersion polymerization using enzyme as catalyst. Chem. Lett. 1995, 24, 795–796.
[104]
Uyama, H. Enzymatic polymerization. In Future Directions in Biocatalysis; Matsuda, T., Ed.; Elsevier Science: Cambridge, MA, USA, 2007; pp. 1–2.
[105]
Reihmann, M.; Ritter, H. Synthesis of phenol polymers using peroxidases. Adv. Polym. Sci. 2006, 194, 1–49, doi:10.1007/12_034.
[106]
Kobayashi, S.; Uyama, H.; Ikeda, R. Artificial Urushi. Chem. Eur. J. 2001, 7, 4755–4760.
[107]
Kim, Y.H.; An, E.S.; Song, B.K.; Kim, D.S.; Chelikani, R. Polymerization of cardanol using soybean peroxidase and its potential application as anti-biofilm coating material. Biotechnol. Lett. 2003, 25, 1521–1524, doi:10.1023/A:1025486617312.
Kadota, J.; Fukuoka, T.; Uyama, H.; Hasegawa, K.; Kobayashi, S. New Positive-type photoresists based on enzymatically synthesized polyphenols. Macromol. Rapid Commun. 2004, 25, 441–444, doi:10.1002/marc.200300045.
[110]
Antoniotti, S.; Santhanam, L.; Ahuja, D.; Hogg, M.G.; Dordick, J.S. Structural diversity of peroxidase-catalyzed oxidation products of o-methoxyphenols. Org. Lett. 2004, 6, 1975–1978, doi:10.1021/ol049448l.
[111]
Mita, N.; Tawaki, S.I.; Uyama, H.; Kobayashi, S. Laccase-catalyzed oxidative polymerization of phenols. Macromol. Biosci. 2003, 3, 253–257, doi:10.1002/mabi.200390032.
[112]
Ikeda, R.; Sugihara, J.; Uyama, H.; Kobayashi, S. Poly(2,6-dihydroxy-l,4-oxyphenylene synthesis of a new poly(phenylene oxide) derivative. Polym. Bull. 1997, 38, 273–277, doi:10.1007/s002890050048.
[113]
Ikeda, R.; Sugihara, J.; Uyama, H.; Kobayashi, S. Enzymatic oxidative polymerization of 2,6-dimethylphenol. Macromolecules 1996, 29, 8702–8705, doi:10.1021/ma961055h.
[114]
Uyama, H.; Kurioka, H.; Sugihara, J.; Komatsu, I.; Kobayashi, S. Oxidative polymerization of p-alkylphenols catalyzed by horseradish peroxidase. J. Polym. Sci. Pol. Chem. 1997, 35, 1453–1459, doi:10.1002/(SICI)1099-0518(199706)35:8<1453::AID-POLA14>3.0.CO;2-6.
[115]
Wang, P.; Martin, B.D.; Parida, S.; Rethwisch, D.G.; Dordick, J.S. Multienzymic synthesis of poly(hydroquinone) for use as a redox polymer. J. Am. Chem. Soc. 1995, 117, 12885–12886, doi:10.1021/ja00156a037.
[116]
Akkara, J.A.; Senecal, K.J.; Kaplan, D.L. Synthesis and characterization of polymers produced by horseradish peroxidase in dioxane. J. Polym. Sci. Pol. Chem. 1991, 29, 1561–1574, doi:10.1002/pola.1991.080291105.
[117]
Akita, M.; Tsutsumi, D.; Kobayashi, M.; Kise, H. Structural change and catalytic activity of horseradish peroxidase in oxidative polymerization of phenol. Biosci. Biotech. Bioch. 2001, 65, 1581–1588, doi:10.1271/bbb.65.1581.
[118]
Angerer, P.S.; Studer, A.; Witholt, B.; Li, Z. Oxidative polymerization of a substituted phenol with ion-paired horseradish peroxidase in an organic solvent. Macromolecules 2005, 38, 6248–6250, doi:10.1021/ma050082h.
[119]
Eker, B.; Zagorevski, D.; Zhu, G.; Linhardt, R.J.; Dordick, J.S. Enzymatic polymerization of phenols in room-temperature ionic liquids. J. Mol. Catal. B Enzym. 2009, 59, 177–184, doi:10.1016/j.molcatb.2009.02.018.
[120]
Mita, N.; Tawaki, S.; Uyama, H.; Kobayashi, S. Enzymatic oxidative polymerization of phenol in an aqueous solution in the presence of a catalytic amount of cyclodextrin. Macromol. Biosci. 2002, 3, 127–130.
[121]
Kim, Y.J.; Uyama, H.; Kobayashi, S. Regioselective synthesis of poly(phenylene) as a complex with poly(ethylene glycol) by template polymerization of phenol in water. Macromolecules 2003, 36, 5058–5060, doi:10.1021/ma0342022.
[122]
Kommareddi, N.S.; Tata, M.; Karayigitoglu, C.; John, V.T.; McPherson, G.L.; Herman, M.F.; Oconnor, C.J.; Lee, Y.S.; Akkara, J.A.; Kaplan, D.L. Enzymatic polymerizations using surfactant microstructures and the preparation of polymer-ferrite composites. Appl. Biochem. Biotechnol. 1995, 51–52, 241–252, doi:10.1007/BF02933427.
[123]
Ghan, R.; Shutava, T.; Patel, A.; John, V.T.; Lvov, Y. Enzyme-catalyzed polymerization of phenols within polyelectrolyte microcapsules. Macromolecules 2004, 37, 4519–4524.
[124]
Marín, F.R.; Frutos, M.J.; Pérez-Alvarez, J.A.; Martinez-Sánchez, F.; del Río, J.A. Flavonoids as nutraceuticals: Structural related antioxidant properties and their role on ascorbic acid preservation. Stud. Nat. Prod. Chem. 2002, 26, 741–778, doi:10.1016/S1572-5995(02)80018-7.
[125]
Di Carlo, G.; Mascolo, N.; Izzo, A.A.; Capasso, F. Flavonoids: Old and new aspects of a class of natural therapeutic drugs. Life Sci. 1999, 65, 337–353, doi:10.1016/S0024-3205(99)00120-4.
[126]
Rice-Evans, C.A.; Miller, N.J.; Paganga, G. Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radic. Biol. Med. 1996, 20, 933–956, doi:10.1016/0891-5849(95)02227-9.
[127]
Flavonoids in Biology and Medicine III—Current Issues in Flavonoids Research; Das, N.P., Cheeseman, K.H., Eds.; Informa Healthcare: London, UK, 1991; Volume 14, pp. 77–78.
[128]
Mejias, L.; Reihmann, M.H.; Sepulveda-Boza, S.; Ritter, H. New polymers from natural phenols using horseradish or soybean peroxidase. Macromol. Biosci. 2002, 2, 24–32, doi:10.1002/1616-5195(20020101)2:1<24::AID-MABI24>3.0.CO;2-6.
[129]
Kurisawa, M.; Chung, J.E.; Uyama, H.; Kobayashi, S. Laccase-catalyzed synthesis and antioxidant property of poly(catechin). Macromol. Biosci. 2003, 3, 758–764, doi:10.1002/mabi.200300038.
[130]
Kurisawa, M.; Chung, J.E.; Uyama, H.; Kobayashi, S. Oxidative coupling of epigallocatechin gallate amplifies antioxidant activity and inhibits xanthine oxidase activity. Chem. Commun. 2004, doi:10.1039/B312311A.
[131]
Kurisawa, M.; Chung, J.E.; Kim, Y.J.; Uyama, H.; Kobayashi, S. Amplification of antioxidant activity and xanthine oxidase inhibition of catechin by enzymatic polymerization. Biomacromolecules 2003, 4, 469–471, doi:10.1021/bm034012z.
[132]
Gon？alves, I.; Matamá, T.; Cavaco-Paulo, A.; Silva, C. Laccase coating of catheters with poly(catechin) for biofilm reduction. Biocatal. Biotransform 2013. in press.
[133]
Kurisawa, M.; Chung, J.E.; Uyama, H.; Kobayashi, S. Enzymatic synthesis and antioxidant properties of poly(rutin). Biomacromolecules 2003, 4, 1394–1399, doi:10.1021/bm034136b.
[134]
Bo？i？, M.; Gorgieva, S.; Kokol, V. Laccase-mediated functionalization of chitosan by caffeic and gallic acids for modulating antioxidant and antimicrobial properties. Carbohyd. Polym. 2012, 87, 2388–2398, doi:10.1016/j.carbpol.2011.11.006.
[135]
Brzonova, I.; Steiner, W.; Zankel, A.; Nyanhongo, G.S. Enzymatic synthesis of catechol and hydroxyl-carboxic acid functionalized chitosan microspheres for iron overload therapy. Eur. J. Pharm. Biopharm. 2011, 79, 294–303, doi:10.1016/j.ejpb.2011.04.018.
[136]
Fras-Zemlji？, L.; Kokol, V.; ？akara, D. Antimicrobial and antioxidant properties of chitosan-based viscose fibres enzymatically functionalized with flavonoids. Text. Res. J. 2011, 81, 1532–1540, doi:10.1177/0040517511404600.
[137]
Sousa, F.; Guebitz, G.M.; Kokol, V. Antimicrobial and antioxidant properties of chitosan enzymatically functionalized with flavonoids. Process Biochem. 2009, 44, 749–756, doi:10.1016/j.procbio.2009.03.009.
[138]
Pina-Luis, G.; Rosquete-Pina, G.; Valdés, A.C.; Ochoa, A.; Rivero, I.; Díaz-García, M.E. Morin functionalized Merrifield’s resin: A new material for enrichment and sensing heavy metals. React. Funct. Polym. 2012, 72, 61–68, doi:10.1016/j.reactfunctpolym.2011.10.003.
[139]
Donato, L.; Chiappetta, G.; Drioli, E. Naringin-imprinted polymer layer using photo polymerization method. Sep. Sci. Technol. 2011, 46, 1555–1562, doi:10.1080/01496395.2011.575429.
[140]
Spizzirri, U.G.; Parisi, O.I.; Iemma, F.; Cirillo, G.; Puoci, F.; Curcio, M.; Picci, N. Antioxidant-polysaccharide conjugates for food application by eco-friendly grafting procedure. Carbohyd. Polym. 2010, 79, 333–334, doi:10.1016/j.carbpol.2009.08.010.
[141]
Jaeger, K.E.; Eggert, T. Lipases for biotechnology. Curr. Opin. Biotechnol. 2002, 13, 390–397.
[142]
Sharma, R.; Chisti, Y.; Banerjee, U.C. Production, purification, characterization and applications of lipases. Biotechnol. Adv. 2001, 19, 627–662, doi:10.1016/S0734-9750(01)00086-6.
[143]
Yu, Y.; Wu, D.; Liu, C.; Zhao, Z.; Yang, Y.; Li, Q. Lipase/esterase-catalyzed synthesis of aliphatic polyesters via polycondensation: A review. Process Biochem. 2012, 47, 1027–1036, doi:10.1016/j.procbio.2012.04.006.
[144]
Yang, Y.; Yu, Y.; Zhang, Y.; Liu, C.; Shi, W.; Li, Q. Lipase/esterase-catalyzed ring-opening polymerization: A green polyester synthesis technique. Process Biochem. 2011, 46, 1900–1908, doi:10.1016/j.procbio.2011.07.016.
[145]
He, F.; Wang, Y.P.; Liu, G.; Jia, H.L.; Feng, J.; Zhuo, R.X. Synthesis, characterization and ring-opening polymerization of a novel six-membered cyclic carbonate bearing pendent allyl ether group. Polymer 2008, 49, 1185–1190, doi:10.1016/j.polymer.2008.01.025.
[146]
Runge, M.; O’Hagan, D.; Haufe, G. Lipase-catalyzed polymerization of fluorinated lactones and fluorinated hydroxycarboxylic acids. J. Polym. Sci. Pol. Chem. 2000, 38, 2004–2012, doi:10.1002/(SICI)1099-0518(20000601)38:11<2004::AID-POLA90>3.0.CO;2-T.
[147]
Zinck, P. One-step synthesis of polyesters specialties for biomedical applications. Rev. Environ. Sci. Biotechnol. 2009, 8, 231–234, doi:10.1007/s11157-009-9168-9.
[148]
Kobayashi, S.; Makino, A. Enzymatic polymer synthesis: An opportunity for green polymer chemistry. Chem. Rev. 2009, 109, 5288–5353, doi:10.1021/cr900165z.
[149]
Uyama, H.; Takamoto, T.; Kobayashi, S. Enzymatic synthesis of polyesters in ionic liquids. Polym. J. 2002, 34, 94–96, doi:10.1295/polymj.34.94.
[150]
Chaudhary, A.K.; Beckman, E.J.; Russell, A.J. Rational control of polymer molecular weight and dispersity during enzyme-catalyzed polyester synthesis in supercritical fluids. J. Am. Chem. Soc. 1995, 117, 3728–3733, doi:10.1021/ja00118a009.
[151]
Okumura, S.; Iwai, M.; Tominaga, T. Synthesis of ester oligomer by Aspergillus niger lipase. Agr. Biol. Chem. (Tokyo) 1984, 48, 2805–2813, doi:10.1271/bbb1961.48.2805.
Linko, Y.Y.; Seppala, J. Producing high molecular weight biodegradable polyesters. Chem. Tech. 1996, 26, 25–31.
[154]
Go？mez-Patin？o, M.B.; Cassani, J.; Jaramillo-Flores, M.E.; Zepeda-Vallejo, L.G.; Sandoval, G.; Jimenez-Estrada, M.; Arrieta-Baez, D. Oligomerization of 10,16-dihydroxyhexadecanoic acid and methyl 10,16-dihydroxyhexadecanoate catalyzed by lipases. Molecules 2013, 18, 9317–9333, doi:10.3390/molecules18089317.
[155]
Kobayashi, S.; Uyama, H.; Suda, S.; Namekawa, S. Dehydration polymerization in aqueous medium catalyzed by lipase. Chem. Lett. 1997, 26, 105–107, doi:10.1246/cl.1997.105.
[156]
Poojari, Y.; Palsule, A.S.; Cai, M.; Clarson, S.J.; Gross, R.A. Synthesis of organosiloxane copolymers using enzymatic polyesterification. Eur. Polym. J. 2008, 44, 4139–4145, doi:10.1016/j.eurpolymj.2008.07.043.
[157]
Yang, Y.; Lu, W.; Cai, J.; Hou, Y.; Ouyang, S.; Xie, W.; Gross, R.A. Poly(oleicdiacid-co-glycerol): Comparison of polymer structure resulting from chemical and lipase catalysis. Macromolecules 2011, 44, 1977–1985, doi:10.1021/ma102939k.
Fehling, E.; Bergander, K.; Klein, E.; Weber, N.; Vosmann, K. Thiol-functionalized copolymeric polyesters by lipase-catalyzed esterification and transesterification of 1,12-dodecanedioic acid and its diethyl ester, respectively, with 1-thioglycerol. Biotechnol. Lett. 2010, 32, 1463–1471, doi:10.1007/s10529-010-0311-z.
Uyama, H.; Kobayashi, S. Enzymatic synthesis of polyesters via polycondensation. Adv. Polym. Sci. 2006, 194, 133–158, doi:10.1007/12_031.
[162]
Brazwell, E.M.; Filos, D.Y.; Morrow, C.J. Biocatalytic synthesis of polymers. III. Formation of a high molecular weight polyester through limitation of hydrolysis by enzyme-bound water and through equilibrium control. J. Polym. Sci. Pol. Chem. 1995, 33, 89–95, doi:10.1002/pola.1995.080330111.
[163]
Kobayashi, S. Recent developments in lipase-catalyzed synthesis of polyesters. Macromol. Rapid Commun. 2009, 30, 237–266, doi:10.1002/marc.200800690.
[164]
Azim, H.; Dekhterman, A.; Jiang, Z.; Gross, R.A. Candida antarctica lipase B-catalyzed synthesis of poly(butylene succinate): Shorter chain building blocks also work. Biomacromolecules 2006, 7, 3093–3097, doi:10.1021/bm060574h.
Uyama, H.; Yaguchi, S.; Kobayashi, S. Lipase-catalyzed polycondensation of dicarboxylic acid-divinyl esters and glycols to aliphatic polyesters. J. Polym. Sci. Pol. Chem. 1999, 37, 2737–2745.
[167]
Yao, D.; Li, G.; Kuila, T.; Li, P.; Kim, N.H.; Kim, S.I.; Lee, J.H. Lipase-catalyzed synthesis and characterization of biodegradable polyester containing l-malic acid unit in solvent system. J. Appl. Polym. Sci. 2011, 120, 1114–1120, doi:10.1002/app.33257.
[168]
Steunenberg, P.; Uiterweerd, M.; Sijm, M.; Scott, E.L.; Zuilhof, H.; Sanders, J.P.M.; Franssen, M.C.R. Enzyme-catalyzed polymerization of β-alanine esters, a sustainable route towards the formation of poly-β-alanine. Curr. Org. Chem. 2013, 17, 682–690.
[169]
Kumar, D.; Bhalla, T.C. Microbial proteases in peptide synthesis: Approaches and applications. Appl. Microbiol. Biotechnol. 2005, 68, 726–736, doi:10.1007/s00253-005-0094-7.
[170]
Kuhn, D.; Durrschmidt, P.; Mansfeld, J.; Ulbrich-Hofmann, R. Boilysin and thermolysin in dipeptide synthesis: A comparative study. Biotechnol. Appl. Biochem. 2002, 36, 71–76, doi:10.1042/BA20020012.
[171]
Bille, V.; Ripak, C.; Assche, I.; Forni, L.; Degelaen, J.; Searso, J. Semi-enzymic synthesis of somatostatin. In Proceedings of 21st European Peptide Symposium, Platja d’Aro, Spain, 2–8 September 1990.
[172]
Gu, Q.M.; Maslanka, W.W.; Cheng, H.N. Enzyme-catalyzed polyamides and their derivatives. In Polymer Biocatalysis and Biomaterials II; Cheng, H.N., Gross, R.A., Eds.; ACS Symposium Series 999; Oxford University Press: Washington, DC, USA, 2008; pp. 309–319.
[173]
Poulhe？s, F.; Mouysset, D.; Gil, G.; Bertrand, M.P.; Gastaldi, S. Speeding-up enzyme-catalyzed synthesis of polyamides using ω-amino-a-alkoxy-acetate as monomer. Polymer 2013, 54, 3467–3471, doi:10.1016/j.polymer.2013.05.011.
[174]
Ikeda, R.; Tanaka, H.; Uyama, H.; Kobayashi, S. Laccase-catalyzed polymerization of acrylamide. Macromol. Rapid Commun. 1998, 19, 423–425, doi:10.1002/(SICI)1521-3927(19980801)19:8<423::AID-MARC423>3.0.CO;2-K.
[175]
Hollmann, F.; Gumulya, Y.; T？lle, C.; Liese, A.; Thum, O. Evaluation of the laccase from Myceliophthora thermophila as industrial biocatalyst for polymerization reactions. Macromolecules 2008, 41, 8520–8524, doi:10.1021/ma801763t.
[176]
Emery, O.; Lalot, T.; Brigodiot, M.; Maréchal, E. Free-radical polymerization of acrylamide by horseradish peroxidase-mediated initiation. J. Polym. Sci. Pol. Chem. 1997, 35, 3331–3333, doi:10.1002/(SICI)1099-0518(19971115)35:15<3331::AID-POLA27>3.0.CO;2-B.
[177]
Mucientes, A.E.; Santiago, F.; Carrero, A.M.; Talavera, B. Superabsorbent hydrogels of poly(sodium acrylate) with crude and exfoliated vermiculites. J. Polym. Eng. 2013, 33, 61–69.
[178]
Jones, N.A.; Atkins, E.D.T.; Hill, M.J.; Cooper, S.J.; Franco, L. Chain-folded lamellar crystals of aliphatic polyamides. comparisons between nylons 44, 64, 84, 104, and 124. Macromolecules 1996, 29, 6011–6018, doi:10.1021/ma9603490.
[179]
Ragupathy, L.; Ziener, U.; Dyllick-Brenzinger, R.; von Vacano, B.; Landfester, K. Enzyme-catalyzed polymerizations at higher temperatures: Synthetic methods to produce polyamides and new poly(amide-co-ester)s. J. Mol. Catal. B Enzym. 2012, 76, 94–105, doi:10.1016/j.molcatb.2011.11.019.
Kobayashi, S. Enzymatic polymerization: A new method of polymer synthesis. J. Polym. Sci. Pol. Chem. 1999, 37, 3041–3056, doi:10.1002/(SICI)1099-0518(19990815)37:16<3041::AID-POLA1>3.0.CO;2-V.
[185]
Kobayashi, S.; Uyama, H.; Ohmae, M. Enzymatic polymerization for precision polymer synthesis. Bull. Chem. Soc. Jpn. 2001, 74, 613–635, doi:10.1246/bcsj.74.613.
[186]
Uyama, H.; Kikuchi, H.; Takeya, K.; Kobayashi, S. Lipase-catalyzed ring-opening polymerization and copolymerization of 15-pentadecanolide. Acta Polym. 1996, 47, 357–360, doi:10.1002/actp.1996.010470807.
[187]
Uyama, H.; Takeya, K.; Kobayashi, S. Enzymatic ring-opening polymerization of lactones to polyesters by lipase catalyst: Unusually high reactivity of macrolides. Bull. Chem. Soc. Jpn. 1995, 68, 56–61, doi:10.1246/bcsj.68.56.
[188]
Uyama, H.; Takeya, K.; Hoshi, N.; Kobayashi, S. Lipase-catalyzed ring-opening polymerization of 12-dodecanolide. Macromolecules 1995, 28, 7046–7050, doi:10.1021/ma00125a002.
Hunsen, M.; Azim, A.; Mang, H.; Wallner, S.R.; Ronkvist, A.; Xie, W.C.; Gross, R.A. A cutinase with polyester synthesis activity. Macromolecules 2007, 40, 148–150, doi:10.1021/ma062095g.
[191]
Nishida, H.; Yamashita, M.; Nagashima, M.; Endo, T.; Tokiwa, Y. Synthesis of metal-free poly(1,4-dioxan-2-one) by enzyme-catalyzed ring-opening polymerization. J. Polym. Sci. Pol. Chem. 2000, 38, 1560–1567, doi:10.1002/(SICI)1099-0518(20000501)38:9<1560::AID-POLA20>3.0.CO;2-F.
[192]
Jiang, Z.; Azim, H. Lipase-catalyzed copolymerization of ω-pentadecalactone with p-dioxanone and characterization of copolymer thermal and crystalline properties. Biomacromolecules 2007, 8, 2262–2269, doi:10.1021/bm070138a.
[193]
Fickers, P.; Marty, A.; Nicaud, J.M. The lipases from Yarrowia lipolytica: Genetics, production, regulation, biochemical characterization and biotechnological applications. Biotechnol. Adv. 2011, 29, 632–644, doi:10.1016/j.biotechadv.2011.04.005.
[194]
Uyama, H.; Kikuchi, H.; Takeya, K.; Hoshi, N.; Kobayashi, S. Immobilized lipase showing high catalytic activity toward enzymatic ring-opening polymerization of macrolides. Chem. Lett. 1996, 25, 107–108.
[195]
Kobayashi, S.; Uyama, H. Precision enzymatic polymerization to polyesters with lipase catalysts. Macromol. Symp. 1999, 144, 237–246, doi:10.1002/masy.19991440121.
[196]
Kobayashi, S.; Uyama, H.; Namekawa, S. In vitro biosynthesis of polyesters with isolated enzymes in aqueous systems and organic solvents. Polym. Degrad. Stabil. 1998, 59, 195–201, doi:10.1016/S0141-3910(97)00178-X.
[197]
Kumar, A.; Kalra, B.; Dekhterman, A.; Gross, R.A. Efficient ring-opening polymerization and copolymerization of ε-caprolactone and ω-pentadecalactone catalyzed by Candida antartica lipase B. Macromolecules 2000, 33, 6303–6309, doi:10.1021/ma000344+.
[198]
Kobayashi, S.; Uyama, H.; Namekawa, S.; Hayakawa, H. Enzymatic ring-opening polymerization and copolymerization of 8-octanolide by lipase catalyst. Macromolecules 1998, 31, 5655–5659.
[199]
Namekawa, S.; Uyama, H.; Kobayashi, S. Lipase-catalyzed ring-opening polymerization of 16-hexadecanolide. P. Jpn. Acad. B 1998, 74, 65–68, doi:10.2183/pjab.74.65.
[200]
Ebata, H.; Toshima, K.; Matsumura, S. Lipase-catalyzed transformation of poly(ε-caprolactone) into cyclic dicaprolactone. Biomacromolecules 2000, 1, 511–514, doi:10.1021/bm000059y.
[201]
Sugihara, S.; Toshima, K.; Matsumura, S. New strategy for enzymatic synthesis of high-molecular-weight poly(butylene succinate) via cyclic oligomers. Macromol. Rapid Commun. 2006, 27, 203–207, doi:10.1002/marc.200500723.
[202]
Kikuchi, H.; Uyama, H.; Kobayashi, S. Lipase-catalyzed ring-opening polymerization of substituted lactones. Polym. J. 2002, 34, 835–893, doi:10.1295/polymj.34.835.
[203]
Küllmer, K.; Kikuchi, H.; Uyama, H.; Kobayashi, S. Lipase-catalyzed ring-opening polymerization of α-methyl-δ-valerolactone and α-methyl-ε-caprolacton. Macromol. Rapid. Commun. 1998, 19, 127–130, doi:10.1002/marc.1998.030190210.
[204]
Cordova, A.; Iversen, T.; Martinelle, M. Lipase-catalysed formation of macrocycles by ring-opening polymerisation of ？-caprolactone. Polymer 1998, 39, 6519–6524, doi:10.1016/S0032-3861(98)00068-8.
[205]
Namekawa, S.; Uyama, H.; Kobayashi, S. Lipase-catalyzed ring-opening and copolymerization of β-propiolactione. Polym. J. 1996, 28, 730–731, doi:10.1295/polymj.28.730.
[206]
Suzuki, Y.; Taguchi, S.; Hisano, T.; Toshima, K.; Matsumura, S.; Doi, Y. Correlation between structure of the lactones and substrate specificity in enzyme-catalyzed polymerization for the synthesis of polyesters. Biomacromolecules 2003, 4, 537–543, doi:10.1021/bm025688h.
[207]
Nagasawa, T.; Shimizu, H.; Yamada, H. The superiority of the third-generation catalyst, Rhodococcus rhodochrous J1 nitrile hydratase, for industrial production of acrylamide. Appl. Microbiol. Biotechnol. 1993, 40, 189–195.
[208]
Thomas, S.M.; DiCosimo, R.; Nagarajan, V. Biocatalysis: Applications and potentials for the chemical industry. Trends Biotechnol. 2002, 20, 238–242, doi:10.1016/S0167-7799(02)01935-2.
[209]
Chassin, C. A biotechnological process for the production of nicotinamide. Chim. Oggi. 1996, 14, 9–12.
[210]
Nagasawa, T.; Matthew, C.D.; Mauger, J.; Yamada, H. Nitrile hydratase-catalyzed production of nicotinamide from 3-cyanopyridine in Rhodococcus rhodochrous J1. Appl. Environ. Microbiol. 1988, 54, 1766–1769.
[211]
Robins, K.T.; Nagasawa, T. Process for Preparing Amides. PCT Int. Appl. US 7,666,635 B2, 23 February 2010.
[212]
Heveling, J.; Armbruster, E.; Utiger, L.; Rhoner, M.; Dettwiler, H.R.; Chuck, R.J. Process for Preparing Nicotinamide. US Patent 5,719,045, 17 February 1998.
[213]
Straathof, A.J.J. Transformation of biomass into commodity chemicals using enzymes or cells. Chem. Rev. 2013, doi:10.1021/cr400309c.
[214]
Vuyyuru, K.R.; Strasser, P. Oxidation of biomass derived 5-hydroxymethylfurfural using heterogeneous and electrochemical catalysis. Catal. Today 2012, 195, 144–154, doi:10.1016/j.cattod.2012.05.008.
[215]
Casanova, O.; Iborra, S.; Corma, A. Biomass into chemicals: Aerobic oxidation of 5-hydroxymethyl-2-furfural into 2,5-furandicarboxylic acid with gold nanoparticle catalysts. ChemSusChem 2009, 2, 1138–1144, doi:10.1002/cssc.200900137.
[216]
Koopman, F.; Wierckx, N.; de Winde, J.H.; Ruijssenaars, H.J. Efficient whole-cell biotransformation of 5-(hydroxymethyl)furfural into FDCA, 2,5-furandicarboxylic acid. Bioresour. Technol. 2010, 101, 6291–6296, doi:10.1016/j.biortech.2010.03.050.
[217]
Krystof, M.; Pérez-Sánchez, M.; Domínguez de María, P. Lipase-mediated selective oxidation of furfural and 5-hydroxymethylfurfural. ChemSusChem 2013, 6, 826–830, doi:10.1002/cssc.201200954.
[218]
Van Deurzen, M.P.J.; van Rantwijk, F.; Sheldon, R.A. Chloroperoxidase-catalyzed oxidation of 5-hydroxymethylfurfural. J. Carbohydr. Chem. 1997, 16, 299–309.
[219]
Panke, S.; Wubbolts, M. Advances in biocatalytic synthesis of pharmaceutical intermediates. Curr. Opin. Chem. Biol. 2005, 9, 188–194, doi:10.1016/j.cbpa.2005.02.007.
[220]
Ooshima, H.; Mori, H.; Harano, Y. Synthesis of aspartame precursor by solid thermolysin in organic solvent. Biotechnol. Lett. 1985, 7, 789–792, doi:10.1007/BF01025555.
[221]
Griengl, H.; Klempier, N.; Pochlauer, P.; Schmidt, M.; Shi, N.Y.; Zabelinskaja-Mackova, A.A. Enzyme catalysed formation of (S)-cyanohydrins derived from aldehydes and ketones in a biphasic solvent system. Tetrahedron 1998, 54, 14477–14486.
Fritz, I.B. Action of carnitine on long chain fatty acid oxidation by liver. Am. J. Physiol. 1959, 197, 297–304.
[224]
Meyer, H.P.; Kiener, A.; Imwinkelried, R.; Shaw, N. Biotransformations for fine chemicals production. Chimia 1997, 51, 287–289.
[225]
Bommarius, A.S.; Schwarm, M.; Stingl, K.; Kottenhahn, M.; Huthmacher, K.; Drauz, K. Synthesis and use of enantiomerically pure tert-leucine. Tetrahedron Asymmetry 1995, 6, 2851–2888.
[226]
Menzel, A.; Werner, H.; Altenbuchner, J.; Gro？ger, H. From enzymes to “designer bugs” in reductive amination: A new process for the synthesis of l-tert-leucine using a whole cell-catalyst. Eng. Life Sci. 2004, 4, 573–576, doi:10.1002/elsc.200402162.
[227]
Krix, G.; Bommarius, A.S.; Drauz, K.; Kottenhahn, M.; Schwarm, M.; Kula, M.R. Enzymatic reduction of α-keto acids leading to l-amino acids, d- or l-hydroxy acids. J. Biotechnol. 1997, 53, 29–39, doi:10.1016/S0168-1656(96)01657-4.
[228]
Furuhashi, K. Biological routes to optically active epoxides. In Chirality in Industry; Collins, A.N., Sheldrake, G.N., Crosby, J.C., Eds.; John Wiley & Sons: NJ, USA, 1992; pp. 167–186.
[229]
Li, K.; Frost, J. Synthesis of vanillin from glucose. J. Am. Chem. Soc. 1998, 120, 10545–10546, doi:10.1021/ja9817747.
[230]
Aresta, M.; Quaranta, E.; Liberio, R.; Dileo, C.; Tommasi, I. Enzymatic synthesis of 4-OH-benzoic acid from phenol and CO2: The first example of a biotechnological application of a carboxylase enzyme. Tetrahedron 1998, 54, 8841–8846, doi:10.1016/S0040-4020(98)00475-X.
[231]
Baldessari, A. Lipases as catalysts in synthesis of fine chemicals. In Lipases and Phospholipases. Methods in Molecular Biology; Sandoval, G., Ed.; Springer-Humana Press: New York, NY, USA, 2012; Volume 861, pp. 445–448.
[232]
Pal, S.; Nair, V. Enzymatic synthesis of thymidine using bacterial whole cells and isolated purine nucleoside phosphorylase. Biocatal. Biotransform. 1997, 15, 147–158, doi:10.3109/10242429709003615.
[233]
Liese, A.; Villela-Filho, M. Production of fine chemicals using biocatalysis. Curr. Opin. Biotechnol. 1999, 10, 595–603, doi:10.1016/S0958-1669(99)00040-3.
[234]
Rivera, I.; Mateos, J.C.; Marty, A.; Sandoval, G.; Duquesne, S. Lipase from Carica papaya latex presents high enantioselectivity toward the resolution of prodrug (R,S)-2-bromophenylacetic acid octyl ester. Tetrahedron Lett. 2013, 54, 5523–5526.
