Lipases as efficient catalysts in the synthesis of monomers and polymers with biomedical applications

Current Organic Chemistry

Volumn 17, Issue 7, 2013, Pages 719-743

  Liñares, Guadalupe García ^a   Baldessari, Alicia ^a  

^a UNIVERSIDAD DE BUENOS AIRES   (Argentina)

Author keywords

Biomedical applications; Lipase catalyzed polymerization; Monomers

Indexed keywords

CATALYSIS; FUNCTIONAL POLYMERS; LIPASES; MEDICAL APPLICATIONS; POLYMERIZATION;

BIOMEDICAL APPLICATIONS; CATALYZED POLYMERIZATION; EFFICIENT CATALYSTS; ENZYMATIC POLYMERIZATION; HAZARDS REDUCTIONS; HUMAN CONSUMPTION; LIPASE-CATALYZED; LIPASE-CATALYZED POLYMERIZATION; POLYMER CHEMISTRY; WASTE MINIMIZATION;

MONOMERS;

EID: 84876718139     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/1385272811317070007     Document Type: Review

References (323)

1. Williams, D.F. On the nature of biomaterials. Biomaterials, 2009, 30, 5897-5909.
2. Burg, K.L.; Porter, S.; Kellam J.F. Biomaterial developments for bone tissue engineering. Biomaterials, 2000, 21, 2347-2359.
3. de Groot, K. Bioceramics of Calcium-Phosphate; CRC Press: Boca Raton, 2010.
4. Yao, J.; Radin, S.; Leboy, P.S.; Ducheyne, P. The effect of bioactive glass content on synthesis and bioactivity of composite poly(lactic-co-glycolic acid)/bioactive glass substrate for tissue engineering. Biomaterials, 2005, 26, 1935-1943.
5. Peppas, N.A.; Langer, R. New challenges in biomaterials. Science, 1994, 263, 1715-1720.
6. Williams, D.F. To engineer is to create: the link between engineering and regeneration. Trends Biotechnol., 2006, 24, 4-8.
7. Nicolson, P.C.; Vogt, J. Soft contact lens polymers: an evolution. Biomaterials, 2001, 22, 3273-3283.
8. Ronco, C.; Brendolan, A.; Everard, P.; Irone, M.; Ballestri, M.; Cappelli, G.; Inquaggiatto P.; Bellomo R. Cellulose triacetate: another membrane for continuous renal replacement therapy. J. Nephrol., 1999, 12, 241-247.
9. Puppi, D.; Chiellini, F.; Piras, A.M.; Chiellini, E. Polymeric materials for bone and cartilage repair. Prog. Polym. Sci., 2010, 35, 403-440.
10. Schaffert, D.; Wagner E. Gene therapy progress and prospects: synthetic polymer-based systems. Gene Ther., 2008, 15, 1131-1138.
11. Amsden, B. Curable biodegradable elastomers: emerging biomaterials for drug delivery and tissue engineering. Soft Matter, 2007, 3, 1335-1348.
12. Patel D.; Vandromme, S.E.; Reid, M.E.; Taite, L.J. Synergistic activity of alfa-v-beta 3 integrins and the elastin binding protein enhance cell-matrix interactions on bioactive hydrogel surfaces. Biomacromolecules, 2012, 13, 1420-1428.
13. Tymianski, M. Emerging mechanisms of disrupted celular signaling in brain ischemia. Nature Neurosc., 2011,14, 1369-1373.
14. Arnaout, R.; Stainer, D.Y.R. Developmental Biology: Physics adds a twist to gut looping. Curr. Biol., 2011, 21, R854-R857.
15. U.S. Environmental Protection Agency. Green Chemistry. http://www.epa.gov/greenchemistry
16. Lancaster, M. Green Chemistry: An Introductory Text; Royal Society of Chemistry: London, 2010.
17. Sheldon, R.A.; Arends I.; Hanefeld U. Green Chemistry and Catalysis; Wiley-VCH: Weinheim, 2007.
18. Tao, J.; Kazlauskas, R. Biocatalysis for Green Chemistry and Chemical Process Development; John Wiley & Sons, Inc.: New Jersey, 2011.
19. Bommarius A.S.; Riebel B.R. Biocatalysis, Fundamentals and Applications, Wiley-VCH: Weinheim, 2004.
20. Faber, K. Biotransformations in Organic Chemistry: A textbook, 6th ed.; Springer-Verlag: Berlin, 2011.
21. Gotor V.; Alfonso I.; García Urdiales, E. Asymmetric Organic Synthesis with Enzymes, Wiley-VCH: Weinheim, 2008.
22. Dunn, P.J. The importance of Green Chemistry in process research and development. Chem. Soc. Rev., 2012, 41, 1452-1461.
23. Sheldon, R.A. Fundamentals of green chemistry: efficiency in reaction design. Chem. Soc. Rev. 2012, 41, 1437-1451.
24. Savile C.K.; Janey, J.M.; Mundorff, E.C.; Moore, J.C.; Tam, S.; Jarvis, W.R.; Colbeck, J.C.; Krebber, A.; Fleitz, F.J.; Brands, J.; Devine, P.N.; Huisman, G.W.; Hughes, G.J. Biocatalytic asymmetric synthesis of chiral amines from ketones applied to sitagliptin manufacture. Science, 2010, 329 (5989), 305-309.
25. García-Junceda E. Multi-step Enzyme Catalysis: Biotransformations and Chemoenzymatic synthesis; Wiley-VCH: Weinheim, 2008, pp.124-125.
26. Sheldon, R. Characteristic features and biotechnological applications of cross-linked enzyme aggregates (CLEAs). Appl. Microbiol. Biotechnol., 2011, 92, 467-477.
27. Baldessari, A. Lipases as catalysts in synthesis of fine chemicals. In: Lipases and phospholipases: Methods and Protocols; Springer: New York, 2012; pp. 445-456.
28. Monsalve, L.N.; Rosselli, S.; Bruno, M.; Baldessari, A. Enzyme-catalysed transformations of ent-kaurane diterpenoids. Eur. J. Org. Chem., 2005, 2106-2115.
29. Baldessari, A.; Mangone, C.P. Enzyme-catalysed preparation of novel fatty acid derivatives of pyridoxine with surfactant activity. Biocatal. Biotransform., 2002, 20, 275-279.
30. Mat Radzi, S.; Mustafa, W.A.F.; Othman, S.S.; Noor, H.M. Green synthesis of butyl acetate, a pineapple flavor via lipase-catalyzed reaction. Engin. Technol., 2011, 59, 677-680.
31. Baldessari, A.; Iglesias, L. E. Lipases in Green Chemistry: Acylation and Alcoholysis on Steroids and Nucleosides. In: Lipases and phospholipases: Methods and Protocols; Springer: New York, 2012; pp. 457-470.
32. Gotor-Fernández, V.; Busto, E.; Gotor, V. Candida antarctica lipase B: An ideal biocatalyst for the preparation of nitrogenated organic compounds. Adv. Synth. Catal., 2006, 348 (7-8), 797-812.
33. Kobayashi, S., Ritter, H. and Kaplan, D. Enzyme-catalyzed synthesis of polymers. Adv. Polym. Sci. Special issue: Vol. 194, Springer, Berlin, 2006.
34. Kobayashi, S.; Uyama, H.; Kimura, S. Enzymatic polymerization. Chem. Rev., 2001, 101, 3793-3818.
35. Gross, R.A.; Cheng, H.N. Biocatalysis in Polymer Science. American Chemical Society: Washington, 2002.
36. Kobayashi, S.; Makino, A. Enzymatic polymer synthesis: an opportunity for green polymer chemistry. Chem. Rev. 2009, 109, 5288-5353.
37. Palmans, A.R.A.; Heise, A. Enzymatic Polymerisation. Springer: Berlin, 2010.
38. Reihmann, M.; Ritter, J. Synthesis of phenol polymers using peroxidases. In: Enzymed-catalyzed synthesis of polymers; Kobayashi, S.; Ritter, H.; Kaplan, D, Eds.; Springer Verlag: Berlin, 2006, pp. 1-49.
39. Ravichandran, S.; Nagarajan, S.; Ku, B.C.; Coughlin, B.; Emrick, T.; Kumar, J.; Nagarajan, R. Halogen-free ultra-high flame retardant polymers through enzyme catalysis. Green Chemistry, 2012, 14, 819-824.
40. Xu, P.; Singh, A.; Kaplan D.L. Enzymatic catalysis in the synthesis of polyanilines and derivatives of polyanilines. In: Enzymed-catalyzed synthesis of polymers; Kobayashi, S.; Ritter, H.; Kaplan, D, Eds.; Springer Verlag: Berlin, 2006, pp. 69-94.
41. Streltsov, A.V.; Morozova, O.V.; Arkharova, N.A.; Klechkovskaya, V.V.; Staroverova, I.N.; Shumakovich, G.P.; Yaropolov, A.I. Synthesis and characterization of conducting polyaniline prepared by laccase-catalyzed method in sodium dodecylbenzenesulfonate micellar solutions. J. Appl. Pol. Sci., 2009, 114, 928-934.
42. Odian, J. Phenolic polymers. In: Principles of Polymerization, 3rd ed.; John Wiley & Sons: New York, 1991, pp. 125-132.
43. Diao, M.; Quedraogo, N.; Moussa L.B.; Savadogo, P.W.; N'Guessan, A.; Bassole, I.H.M; Dicko, M.H. Biodepollution of wastewater containing phenolic compounds from leather industry by plant peroxidases. Biodegradation, 2011, 22, 389-396.
44. Nestl, B.M.; Nebel, B.A.; Hauer B. Recent progress in industrial biocatalysis. Curr. Op. Chem. Biol., 2011, 15, 187-193.
45. Samuelson, L.A.; Bruno F.; Tripathy, S.K.; Tripathy, S. Nagarajan R.; Kumar, J.; Liu W. Enzymatic polymerization. U.S.Patent 2004/0023346 A1, Feb 4, 2004.
46. Faucher, S. Macro-photoinitiator via enzymatic polymerization. U.S. Patent 2011/0130481 A1, Jun 2, 2011.
47. Zou, J.; Kaplan, D.L.; Wong, P.Y. Method for polymer synthesis using microfluidic enzymatic cascade. U.S. Patent 2009/0298139 A1, Dec 3, 2009.
48. Webb, E.C. Enzyme nomenclature 1992. Reommendations of the nomenclature committee or the International Union of Biocehmistry and Molecular Biology on the nomenclature and classification of enzymes; Academic press: San Diego, 1992, pp. xiii
49. Kobayashi, S.; Ohmae, M. Enzymatic polymerization to polysaccharides. In: Enzymed-catalyzed synthesis of polymers; Kobayashi, S.; Ritter, H.; Kaplan, D. Eds.; Springer Verlag: Berlin, 2006, pp. 159-210.
50. Wu, L.Q.; Bentley, W.E.; Payne, G.F. Biofabrication with biopolymers and enzymes: Potential for constructing scaffolds from soft matter. Int. J. Artif. Organs, 2011, 34, 215-224.
51. Kobayashi, S. Lipase-catalyzed polyester synthesis-A green polymer chemistry. Proc. Jpn. Acad.; Ser. B., 2010, 86, 338-365.
52. Idris, A.; Bukhari, A. Immobilized Candida antarctica lipase B: Hydration, stripping off and application in ring opening polyester synthesis. Biotechnol. Adv., 2012, 30, 550-563.
53. Varma, I.K.; Albertsson, A.C.; Rajkhowa, R.; Srivastava, R.K. Prog. Polym. Sci., 2005, 30, 949-981.
54. Albertsson, A.C.; Srivastava, R.K. Recent developments in enzymecatalyzed ring-opening polymerization. Adv. Drug Delivery Rev., 2008, 60, 1077-1093.
55. Carrea, G.; Riva, S. Organic Synthesis with Enzymes in Non-aqueous Media. Wiley-VCH: Weinheim, 2008.
56. Kapoor, M.; Gupta, M.N. Lipase promiscuity and its biochemical applications. Process Biochemistry, 2012, 47, 555-569.
57. Busto, E.; Gotor-Fernández, V.; Gotor, V. Hydrolases: catalytically promiscuous enzymes for non-conventional reactions in organic synthesis. Chem Soc. Rev., 2010, 39, 4504-4523.
58. Wu, Q.; Liu, B.K.; Lin, X.F. Enzymatic promiscuity for organic synthesis and cascade process. Curr. Org. Chem., 2010, 14, 1966-1988.
59. Humble, M.S.; Berglund, P. Biocatalytic promiscuity. Eur. J. Org. Chem., 2011, 3391-3401.
60. Morrone, R.; Nicolosi, G.; Patti, A.; Piattelli, M. Resolution of racemic flurbiprofen by lipase-mediated esterification in organic solvent. Tetrahedron: Asymm., 1995, 6, 1773-1778.
61. Kralovec, J. A.; Zhang, S.; Zhang, W.; Barrow, C.J. A review of the progress in enzymatic concentration and microencapsulation of omega-3 rich oil from fish and microbial sources. Food Chem., 2012, 131, 639-644.
62. Gog, A.; Roman M.; Tos, M.; Paizs, C.; Irimie, F.D. Biodiesel production using enzymatic transesterification: Current state and perspectives. Renew. Energy, 2012, 39, 10-16.
63. Metzger, J.O.; Bornscheuer, U. Lipids as renewable resources: Current state of chemical and biotechnological conversion and diversification. Appl. Microbiol. Biotechnol. 2006, 71, 13-22.
64. Theil, F. Lipase-supported synthesis of biologically active compounds. Chem. Rev., 1995, 95, 2203-2227.
65. Jaeger, K.E.; Reetz, M.T. Microbial lipases from versatile tolos for biotechnology. Trends. Biotechnol., 1998, 16, 396-403.
66. Basheer, S.M.; Chellapan, S.; Beena, P.S.; Sukumaran, R.K.; Elyas, K.K.; Chandrasekaran, M. Lipase from marine Aspergillus awamori BTMFW032: Production, partial purification and application in oil effluent treatment. New Biotechnol., 2011, 28, 627-638.
67. Bajpai, P. Application of enzymes in the pulp and paper industry. Biotechnol. Prog., 1999, 15, 147-157.
68. Chen, B.; Miller M.E.; Miller L.; Maikner, J.J.; Gross, R.A. Effects of macroporous resin size on Candida antarctica lipase B adsorption, fraction of active molecules, and catalytic activity for polyester synthesis. Langmuir, 2007, 23, 1381-1387.
69. Rivera I.; Mateos-Diaz, J.C.; Sandoval, G. Plant lipases: Partial purification of Carica papaya lipase. In: Lipases and phospholipases: Methods and Protocols; Springer: New York, 2012; pp. 115-122.
70. Salihua, A.; Zahangir, A.; Karima I.A.; Salleha, H.M. Lipase production: An insight in the utilization of renewable agricultural residues. Resour. Conserv. Recycling, 2012, 58, 36-44.
71. Matsumura S. Enzymatic synthesis of polyesters via ring-opening polymerization. Adv Polym Sci., 2006, 194, 95-132.
72. Jiang, Z.; Azim, H.; Gross, R.A.; Focarete, M.L.; Scandola, M. Lipasecatalyzed copolymerization of omega-pentadecalactone with p-dioxanone and characterization of copolymer thermal and crystalline properties. Biomacromolecules, 2007, 8, 2262-2269.
73. Liu, J.; Jiang, Z.; Zhang, S.; Liu, C.; Gross, R.A.; Kyriakides, T.R.; Saltzman, W.M. Biodegradation, biocompatibility and drug delivery in poly(ω-pentadecalactone-co-p-dioxanone) copolyesters. Biomaterials, 2011, 32, 6646-6654.
74. Namekawa, S.; Uyama, H.; Kobayashi, S. Enzymatic synthesis of polyesters from lactones, dicarboxylic acid divinyl esters, and glycols through combinations of ring-opening polymerization and polycondensation. Biomacromolecules, 2000, 1, 335-338.
75. Jiang Z. Lipase-catalyzed synthesis of aliphatic polyesters via copolymerization of lactone, dialkyl diester, and diol. Biomacromolecules, 2008,9, 3246-3251.
76. Mazzocchetti, L.; Scandola, M.; Jiang, Z. Enzymatic synthetic and structural and thermal properties of poly(ω-pentadecalactone-co-butylene-cosuccinate). Macromolecules, 2009, 42, 7811-7819.
77. Liu, J.; Jiang, Z.; Zhang, S.; Saltzman, W.M. Poly(ω-pentadecalactone-cobutylene-co-succinate nanoparticles as biodegradable carriers for camptothecin delivery. Biomaterials, 2009, 30, 5707-5019.
78. Uyama, H.; Kobayashi, S. Enzymatic synthesis of polyesters via polycondensation. Adv. Polym. Sci., 2006,194, 133-158.
79. Azim H, Dekhterman A, Jiang Z, Gross RA. Candida antarctica lipase Bcatalyzed synthesis of poly(butylene succinate): shorter chain building blocks also work. Biomacromolecules, 2006, 7, 3093-3097.
80. Jiang, Z.; Liu, C.; Xie, W.; Gross R.A. Controllled lipase-catalyzed synthesis of poly(hexamethylene carbonate). Macromolecules, 2007, 40, 7934-7943.
81. Rodney, R.L.; Stagno, J.L.; Beckman, E.J.; Russell, A.J. Enzymatic synthesis of carbonate monomers and polycarbonates. Biotechnol. Bioeng., 1999, 62, 259-266.
82. Jiang, Z. Lipase-catalyzed copolymerization of dialkyl carbonate with 1,4-butanediol and ω-pentadecalactone: synthesis of poly(ω-pentadecalactoneco-butylene-co-carbonate). Biomacromolecules, 2011, 12, 1912-1919.
83. Jiang, Z.; Liu, C.; Gross, R.A. Lipase-catalyzed synthesis of aliphatic poly(carbonate-co-esters). Macromolecules, 2008, 41, 4671-4680.
84. Zini, E.; Scandola, M.; Jiang, Z.; Liu, C.; Gross, R.A. Aliphatic polyester carbonate copolymers: enzymatic synthesis and solid-state characterization. Macromolecules, 2008, 41, 4681-4687.
85. Gu Q.M.; Maslanka, W.W.; Cheng, H.N. Enzyme-catalyzed polyamides and their derivatives. In: Polymer Biocatalysis and Biomaterials II; Chen, H.N., Ed. ACS symposium Series: Washington, 2008; pp. 309-319.
86. Velter, I.; La Ferla, B.; Nicotra, F. Carbohydrate-based molecular scaffolding. J. Carbohydr. Chem., 2006, 25, 97-138.
87. Varma, A. J.; Kennedy, J. F.; Galgali, P. Synthetic polymers functionalized by carbohydrates: A review. Carbohydr. Polym., 2004, 56, 429-445.
88. Wang, Q.; Dordick, J.S.; Linhardt, R.J. Synthesis and application of carbohydrate-containing polymers. Chem. Mater., 2002, 14, 3232-3244.
89. Torma, V.; Gyenes, T.; Szakacs, Z.; Noszal, B.; Nemethy, A.; Zrinyi, M. Novel amino acid-based polymers for pharmaceutical applications. Polym. Bull., 2007, 59, 311-328.
90. Mori, H.; Iwaya, H.; Nagai, A.; Endo, T. Controlled synthesis of thermoresponsive polymers derived from L-proline via RAFT polymerization. Chem. Commun., 2005, 38, 4872-4874.
91. Chung, I.D.; Britt, P.; Xie, D.; Harth, E.; Mays, J. Synthesis of amino acidbased polymers via atom transfer radical polymerization in aqueous media at ambient temperature. Chem. Commun., 2005, 8, 1046-1048.
92. Bentolila, A.; Vlodavsky, I.; Haloun, C.; Domb, A. J. Synthesis and heparinlike biological activity of amino acid-based polymers. Polym. Adv. Technol., 2000, 11, 377-387.
93. Albertsson, A.C.; Varma, I.K. Recent developments in ring opening polymerization of lactones for biomedical applications. Biomacromolecules, 2003, 4, 1466-1486.
94. Vert, M. Aliphatic polyesters: great degradable polymers that cannot do everything. Biomacromolecules, 2005, 6, 538-546.
95. Edlund, U.; Albertsson, A.C. Degradable polymer microspheres for controlled drug delivery. Adv. Polym. Sci., 2002, 157, 67-112.
96. Coulembier, O.; Degee, P.; Hedrick, J.L.; Dubois, P. From controlled ringopening polymerization to biodegradable aliphatic polyester: Especially poly(beta-malic acid) derivatives. Prog. Polym.Sci., 2006, 31, 723-747.
97. Gross, R. A.; Kumar, A.; Bhanu, K. Polymer Synthesis by In Vitro Enzyme Catalysis. Chem. Rev., 2001, 101, 2097-2124.
98. Uyama, H.; Kobayashi, S. Enzymatic ring-opening polymerization of lactones catalyzed by lipase. Chem. Lett., 1993, 7, 1149-1150.
99. Knani, D.; Gutman, A.L.; Kohn, D.H. Enzymatic polyesterification in organic media. Enzyme-catalyzed synthesis of linear polyesters. I. Condensation polymerization of linear hydroxyesters. II. Ring-opening polymerization of ε-caprolactone. J. Polym. Sci. Part A: Polym. Chem., 1993, 31, 1221-1232.
100. Yeniad, B.; Naik, H.; Heise, A. Lipases in polymer chemistry. Adv. Biochem. Engin./Biotechnol., 2011, 125, 69-95.
101. Yang, Y.; Yua, Y.; Zhang, Y.; Liua, C.; Shia, W.; Li, Q. Lipase/esterasecatalyzed ring-opening polymerization: A green polyester synthesis technique Process Biochemistry, 2011, 46, 1900-1908.
102. Kobayashi, S., Ohmae, M. Polymer synthesis and modification by enzymatic catalysis. In Macromolecular Engineering: Precise Synthesis, Materials Properties, Applications; Matyjaszewski, K., Gnanou, Y. and Leibler, L. Eds.; Wiley-VCH, Weinheim, 2007, pp. 400-477.
103. Kobayashi, S.; Makino, A. Enzymatic polymer synthesis: an opportunity for green polymer chemistry. Chem. Rev., 2009, 109, 5288-5353.
104. Matsumura, S. Enzyme-catalyzed synthesis and chemical recycling of polyesters. Macromol. Biosci., 2002, 2, 105-126.
105. van der Mee, L.; Helmich, F.; de Bruijn, R.; Vekemans, J.; Palmans, A.R.A.; Meijer, E.W. Investigation of lipase-catalyzed ring-opening polymerizations of lactones with various ring sizes: Kinetic evaluation. Macromolecules, 2006, 39, 5021-5027.
106. Duda, A.; Kowalski, A.; Penczek, S.; Uyama, H.; Kobayashi, S. Kinetics of the ring-opening polymerization of 6-, 7-, 9-, 12-, 13-, 16-, and 17-membered lactones. Comparison of chemical and enzymatic polymerizations. Macromolecules, 2002, 35, 4266-4270.
107. Grothe, E.; Moo-Young, M.; Chisti, Y. Fermentation optimization for the production of poly([beta]-hydroxybutyric acid) microbial thermoplastic. Enzyme and Microbial Technology, 1999, 25, 132-141.
108. Zinck, P. One-step synthesis of polyesters specialties for biomedical applications, Reviews in Environmental Science and Biotechnology, 2009, 8, 231-234.
109. Woodruff, M.A.; Hutmacher, D.W. Resorbable composite scaffolds for bone tissue engineering, In: Tissue and Cell Engineering Society Annual Conference (TCES), Manchester, 2010.
110. Nobes, G.A.R.; Kazlauskas, R.J.; Marchessault, R.H. Lipase-catalyzed ringopening polymerization of lactones: a novel route to poly(hydroxyalkanoate)s. Macromolecules, 1996, 29, 4829-4833.
111. Namekawa, S.; Uyama, H.; Kobayashi, S. Lipase-catalyzed ring-opening polymerization and copolymerization of β-propiolactone. Polym. J., 1996, 28, 730-731.
112. Svirkin, Y.Y.; Xu, J.; Gross, R.A.; Kaplan, D.L.; Swift, G. Enzymecatalyzed stereoselective ring-opening polymerization of α-methyl-β-propiolactone. Macromolecules, 1996, 29, 4591-4597.
113. Xie, W.; Li, J.; Chen, D.; Wang, P.G. Ring-opening polymerization of β-butyrolactone by thermophilic lipases. Macromolecules, 1997, 30, 6997-6998.
114. Matsumura, S.; Suzuki, Y.; Tsukada, K.; Toshima, K.; Doi, Y.; Kasuya, K. Lipase catalyzed ring-opening polymerization of &beta-butyrolactone to the cyclic and linear poly(3-hydroxybutyrate). Macromolecules, 1998, 31, 6444-6449
115. Matsumura, S.; Beppu, H.; Nakamura, K.; Osanai, S.; Toshima, K. Preparation of poly(β-malic acid) by enzymatic ring-opening polymerization of benzyl β-malolactonate. Chem. Lett., 1996, 795-796.
116. 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.
117. Kobayashi, S.; Takeya, K.; Suda, S.; Uyama, H. Lipase-catalyzed ringopening polymerization of medium-size lactones to polyesters. Macromol. Chem. Phys., 1998, 199, 1729-36.
118. Kullmer, K.; Kikuchi, H.; Uyama, H.; Kobayashi, S. Lipase-catalyzed ringopening polymerization of α-methyl-γ-valerolactone and a-methyl-ecaprolactone. Macromol. Rapid. Commun., 1998, 19, 127-130.
119. 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. Part A: Polym. Chem., 2000, 38, 1560-1567.
120. Chen, R.Y.; Zhang, Y.R.; Zhang, Y.Z. Synthesis of poly(1,4-dioxan-2-one) catalyzed by immobilized lipase CA. J. Mol. Catal. B: Enzym., 2009, 54, 224-228.
121. Matsumura, S.; Mabuchi, K.; Toshima, K. Lipase-catalyzed ring-opening polymerization of lactide. Macromol. Rapid. Commun., 1997, 18, 477-482.
122. Hans, M.; Keul, M.; Moeller, M. Ring-opening polymerization of dd-lactide catalyzed by Novozyme 435. Macromol. Biosci., 2009, 9, 239-247.
123. Bonduelle, C.; Martin-Vaca, B.; Bourissou, D. Lipase-catalyzed ringopening polymerization of the O-carboxylic anhydride derived from lactic acid. Biomacromolecules, 2009, 10, 3069-3071.
124. Kumar, A.; Gross, R.A. Candida antarctica lipase B catalyzed polycaprolactone synthesis: effects of organic medium and temperature. Biomacromolecules, 2000, 1, 133-138.
125. Mei, Y.; Kumar, A.; Gross, R.A. Probing water-temperature relationships for lipase-catalyzed lactone ring-opening polymerizations. Macromolecules, 2002, 35, 5444-5448
126. Mei, Y.; Kumar, A.; Gross, R.A. Kinetics and mechanism of Candida antarctica lipase B catalyzed solution polymerization of ε-caprolactone. Macromolecules, 2003, 36, 5530-5536.
127. Matsumura, S.; Ebata, H.; Toshima, K. A new strategy for sustainable polymer recycling using an enzyme: Poly(ε-caprolactone). Macromol. Rapid. Commun., 2000, 21, 860-863.
128. Kerep, P.; Ritter, H. Influence of microwave irradiation on the lipasecatalyzed ring-opening polymerization of ε-caprolactone. Macromol. Rapid. Commun., 2006, 27, 707-710.
129. Gorke, J.T.; Okrasa, K.; Louwagie, A.; Kazlauskas, R.J.; Srienc, F. Enzymatic synthesis of poly(hydroxyalkanoates) in ionic liquids, J. Biotech., 2007, 132, 306-313.
130. Gumel, A.M.; Annuar, M.S.M.; Chisti, Y.; Heidelberg, T. Ultrasound assisted lipase catalyzed synthesis of poly-6-hydroxyhexanoate Ultrasonics Sonochemistry, 2012, 19, 659-667.
131. Kikuchi, H.; Uyama, H.; Kobayashi, S. Lipase-catalyzed ring-opening polymerization of substituted lactones. Polym. J., 2002, 34, 835-840.
132. Vaida, C.; Takwa, M.; Martinelle, M.; Hult, K.; Keul, H.; Moller, M. γ-Acyloxy- ε aprolactones: synthesis, ring-opening polymerization vs. rearrangement by means of chemical and enzymatic catalysis. Macromol. Symp., 2008, 272, 28-38.
133. Peeters, J.W.; Veld, M.; Scheijen, F.; Heise, A.; Palmans, A.R.A.; Meijer, E.W. Cascade synthesis of chiral block copolymers combing lipase catalyzed ring opening polymerization and atomic transfer radical polymerization. Biomacromolecules, 2004, 5, 1862-1868
134. Peeters, J.W., van Leeuwen, O.; Palmans, A.R.A.; Meijer, E.W. Lipase-catalyzed ring-opening polymerization of 4-substituted ε-caprolactone: mechanistic considerations. Macromolecules, 2005, 38, 5587-5592.
135. Kobayashi, S.; Uyama, H.; Namekawa, S.; Hayakawa, H. Enzymatic ringopening polymerization and copolymerization of 8-octanolide by lipase catalyst. Macromolecules, 1998, 31, 5655-5659.
136. Uyama, H.; Kikuchi, H.; Takeya, K.; Kobayashi, S. Lipase-catalyzed ring-opening polymerization and copolymerization of 15-pentadecanolide. Acta Polym., 1996, 47, 357-360
137. Uyama, H.; Namekawa, S.; Kobayashi, S. Mechanistic studies on the lipase-catalyzed ring-opening polymerization of lactones. Polym. J., 1997, 29, 299-301.
138. Uyama, H.; Takeya, K.; Hoshi, N.; Kobayashi, S. Lipase-catalyzed ring opening polymerization of 12-dodecanolide. Macromolecules, 1995, 28, 7046-50.
139. Bisht, K.S.; Henderson, L.A.; Gross, R.A.; Kaplan, D.L.; Swift, G. Enzymecatalyzed ring opening polymerization of ω-pentadecalactone. Macromolecules, 1997, 30, 2705-2711.
140. Mueller, S.; Uyama, H.; Kobayashi, S. Lipase-catalyzed ring-opening polymerization of cyclic diesters. Chem. Lett., 1999, 1317-1318.
141. Veld, M. A. J., Palmans, A. R. A. and Meijer, E. W. Selective polymerization of functional monomers with Novozym 435. J. Polym. Sci. Part A: Polym. Chem., 2007, 45, 5968-5978.
142. Nakene, K.; Tamaki, C.; Hata, Y.; Ogihara, T.; Ogata, N. Blends of poly(llactic acid) with poly(ω-pentadecalactone) synthesized by enzyme-catalyzed polymerization. J. Appl. Polym. Sci., 2008, 108, 2139-2143.
143. Ceccorulli, G.; Scandola, M.; Kumar, A.; Kalra, B.; Gross, R.A. Cocrystallization of random copolymers of ω-pentadecalactone and ε-caprolactone synthesized by lipase catalysis. Biomacromolecules, 2005, 6, 902-907.
144. Kumar, A.; Garg, K.; Gross, R.A. Copolymerizations of ω-pentadecalactone and trimethylene carbonate by chemical and lipase catalysis. Macromolecules, 2001, 34, 3527-3533.
145. Meyer, U.; Palmans, A.R.A.; Loontjens, T.; Heise, A. Enzymatic ringopening polymerization and atom transfer radical polymerization from a bifunctional initiator. Macromolecules, 2002, 35, 2873-2875.
146. Van As, B.A.C.; Thomassen, P.; Kalra, B.; Gross, R.A.; Meijer, E.W.; Palmans, A.R.A.; Heise, A. One-pot chemoenzymatic cascade polymerization under kinetic resolution conditions. Macromolecules, 2004, 37, 8973-8977.
147. de Geus, M.; Peeters, J.; Wolffs, M.; Hermans, T.; Palmans, A.R.A.; Koning, C.E.; Heise, A. Investigation of factors influencing the chemoenzymatic synthesis of block copolymers. Macromolecules, 2005, 38, 4220-4225.
148. Hedfors, C.; Östmark, E.; Malmström, E.; Hult, K.; Martinelle, M. Thiol end-functionalization of poly(ε-caprolactone) catalyzed by Candida antarctica lipase B. Macromolecules, 2005, 38, 647-649.
149. Takwa, M.; Simpson, N.; Malmström, E.; Hult, K.; Martinelle, M. Onepot difunctionalization of poly(ω-pentadecalactone) with thiol-thiol or thiolacrylate groups Catalyzed by Candida antarctica lipase B. Macromol. Rapid Commun., 2006, 27, 1932-1936
150. Takwa, M.; Xiao, Y.; Simpson, N.; Malmström, E.; Hult, K.; Koning, C.E.; Heise, A.; Martinelle, M. Lipase catalyzed HEMA initiated ring-opening polymerization: in situ formation of mixed polyester methacrylates by transesterification. Biomacromolecules, 2008, 9, 704-710.
151. Takwa, M.; Hult, K.; Martinelle, M. Single-step, solvent-free enzymatic route to α, ω-functionalized polypentadecalactone macromonomers. Macromolecules, 2008, 41, 5230-5236.
152. Wallace, J.S.; Morrow, C.J. Biocatalytic synthesis of polymers. 2. Preparation of [AA-BB]X polyesters by porcine pancreatic lipase catalyzed transesterification in anhydrous, low polarity organic solvents.J. Pol. Sci. A: Polym. Chem., 1989, 27, 3271-3284.
153. Morrow, C.J.; Wallace, J.S. Synthesis of polyesters by lipase-catalysed polycondensation in organic media In: Biocatalysis; Abramowicz, D.A. Ed.; Van Nostrand Reinhold: New York, 1990, pp. 25-62.
154. Dong, H.; Wang, H.D.; Cao, S.G.; Shen, J.C. Lipase-catalyzed polymerization of lactones and linear hydroxyesters. Biotechnol. Lett., 1998, 20, 905-908
155. Binns, F.; Harffey, P.; Roberts, S.M.; Taylor, A. Studies leading to the large scale synthesis of polyesters using enzymes. J. Chem. Soc. Perkin Trans., 1999, 1, 2671-2676.
156. Mahapatro, A.; Kalra, B.; Kumar, A.; Gross, R.A. Lipase-catalyzed polycondensations: effect of substrates and solvent on chain formation, dispersity, and end-group structure. Biomacromolecules, 2003, 4, 544-551.
157. Kulshrestha, A.S.; Gao, W.; Gross, R.A. Glycerol copolyesters: control of branching and molecular weight using a lipase catalyst. Macromolecules, 2005, 38, 3193-3204
158. Kulshrestha, A.S.; Gao, W.; Fu, H.; Gross, R.A. Synthesis and characterization of branched polymers from lipase-catalyzed trimethylolpropane copolymerizations. Biomacromolecules, 2007, 8, 1794-1801.
159. Sahoo, B.; Bhattacharya, A.; Fu, H.; Gao, W.; Gross, R.A. Influence of PEG end group and molecular weight on its reactivity for lipase-catalyzed polyester synthesis. Biomacromolecules, 2006, 7, 1042-1048.
160. Hu, J.; Gao, W.; Kulshrestha, A.; Gross, R.A. "Sweet Polyesters": lipasecatalyzed condensation-polymerizations of alditols. Macromolecules, 2006, 39, 6789-6792.
161. Duwensee, J.; Wenda, S.; Ruth, W.; Kragl, U. Lipase-catalyzed polycondensation in water: a new approach for polyester synthesis. Org. Proc. Res. Dev., 2010, 14, 48-57.
162. Ajima, A.; Yoshimoto, T.; Takahashi, K.; Tamaura, Y.; Saito, Y.; Inada, Y. Polymerization of 10-hydroxydecanoic acid in benzene with polyethylene glycol-modified lipase. Biotechnol. Lett., 1985, 7, 303-306.
163. Kiran, K.R.; Divakar, S. Lipase-catalysed polymerization of lactic acid and its film forming properties. World J. Microbiol. Biotechnol., 2003, 19, 859-865.
164. Mahapatro, A.; Kumar, A.; Gross, R.A. Mild, solvent-free o-hydroxy acid polycondensations catalyzed by Candida antarctica lipase B. Biomacromolecules, 2004, 5, 62-68.
165. Kulshrestha, A.S.; Sahoo, B.; Gao, W.; Fu, H.; Gross, R.A. Lipase catalysis. A direct route to linear aliphatic copolyesters of bis(hydroxymethyl)butyric acid with pendant carboxylic acid groups. Macromolecules, 2005, 38, 3205-3213.
166. Iglesias, L.E.; Fukuyama, Y.; Nonami, H.; Erra-Balsells, R.; Baldessari, A. A simple enzymatic procedure for the synthesis of a hydroxylated polyester from glycerol and adipic acid. Biotech. Techn., 1999, 13, 923-926.
167. Kumar, A.; Kulshrestha, A.S.; Gao, W.; Gross, R.A. Versatile route to polyol polyesters by lipase catalysis. Macromolecules, 2003, 36, 8219-8221.
168. Kanca, U.; Van Buijtenen, J.; Van As, B.A.C.; Korevaar, P.A.; Vekemans, J.; Palmans, A.R.A.; Meijer, E.W. Iterative tandem catalysis of racemic AB monomers. J. Polym. Sci. Part A: Polym. Chem., 2008, 46, 2721-2733.
169. Okumura, S.; Iwai, M.; Tominaga, Y. Synthesis of ester oligomer by Aspergillus niger lipase. Agri. Biol. Chem., 1984, 48, 2805-2808.
170. Uyama, H.; Takamoto, T.; Kobayashi, S. Enzymatic synthesis of polyesters in ionic liquids. Polym. J., 2002, 34, 94-96.
171. Marcilla, R.; de Geus, M.; Mecerreyes, D.; Duxbury, C.J.; Koning, C.E.; Heise, A. Enzymatic polyester synthesis in ionic liquids. Eur. Polym. J., 2006, 42, 1215-1221.
172. Takamoto, T.; Uyama, H.: Kobayashi, S. Lipase-catalyzed synthesis of aliphatic polyesters in supercritical carbon dioxide. e-Polymers, 2001, 4, 1-6.
173. Uyama, H.; Inada, K.; Kobayashi, S. Enzymatic polymerization of dicarboxylic acid and glycol to polyester in solvent-free system. Chem. Lett., 1998, 1285-1286.
174. Mahapatro, A.; Kalra, B.; Kumar, A.; Gross, R.A. Solvent-free adipic acid/1,8-octanediol condensation polymerizations catalyzed by Candida antartica lipase B. Macromolecules, 2004, 37, 35-40.
175. Hilker, I.; Rabani, G.; Verzijl, G.K.M.; Palmans, A.R.A.; Heise, A. Chiral polyesters by dynamic kinetic resolution polymerization. Angew. Chem. Int. Ed., 2006, 45, 2130-2132.
176. Liu, W.; Chen, B.; Wang, F.; Tan, T.; Deng, L. Lipase-catalyzed synthesis of aliphatic polyesters and properties characterization. Process Biochemistry, 2011, 46, 1993-2000.
177. Linko, Y.Y.; Wang, Z.L.; Seppala, J. Lipase-catalyzed synthesis of poly(1,4-butylsebacate) from sebacic acid or its derivatives with 1,4-butanediol. J. Biotechnol., 1995, 40, 133-138.
178. Sinha, V.R.; Bansal, K.; Kaushik, R.; Kumria, R.; Trehan, A. Poly-ε-caprolactone microspheres and nanospheres: an overview. Int. J. Pharm., 2004, 278, 1-23
179. Belorgey, G.; Sauvet, G. In: Silicone-containing polymers; Jones, R.G.; Wataru, A.; Chojnowski, J., Eds; Kluwer Academic: Netherlands, 2000, pp 43-78.
180. Van Dyke, M.E.; Clarson, S.J.; Arshady, R. In: Introduction to polymeric biomaterials, In: Silicone biomaterials; Arshady, R., Ed.; The PBM series vol 1. Citus Books 2003, pp 109-135.
181. Mark, J.E.; Allcock, H.R.; West, R. Polysiloxanes and related polymers, In: Inorganic polymers. Oxford University Press; 2005, p. 154-189.
182. Hron, P. Hydrophilisation of silicone rubber for medical applications. Polym. Int., 2003, 52, 1531-1539.
183. Clarson, S.J.; Semlyen, J.A. In Siloxane Polymers; Prentice-Hall:Englewood Cliffs, NJ, 1993; p 216
184. Clarson, S.J.; Semlyen, J.A. Studies of cyclic and linear poly(dimethyl-siloxanes): 21. High temperature thermal behaviour. Polymer, 1986, 27, 91-95.
185. Morse, D.E. Silicon biotechnology: harnessing biological silica production to construct new materials. Trends Biotechnol., 1999, 17, 230-232.
186. Iroh, J.O. In: Polymer DataHandbook, Poly(ethylene terephthalate). 2nd ed.; Mark, J.E. Ed.; Oxford University Press: NewYork, 2009; p 706.
187. Ji, Y.Y.; Chang, H.K.; Hong, Y.C.; Lee, S.H. Water-repellent improvement of polyester fiber via radio frequency plasma treatment with argon/ hexamethyldisiloxane (HMDSO) at atmospheric pressure. Curr. Appl. Phys., 2009, 9, 253-256.
188. Sharma, B.; Azim, A.; Azim, H.; Gross, R.A.; Zini, E.; Focarete, M.L.; Scandola, M. Enzymatic Synthesis and solid-state properties of aliphatic polyesteramides with polydimethylsiloxane blocks. Macromolecules, 2007, 40, 7919-7927.
189. Liu, H.J.; Lin, L.H.; Chen, K.M. Polyethylene glycol/polydimethylsiloxane polyester products as leveling agents in nylon dyeing. Text. Res. J., 2003, 73, 583-587.
190. Bishwabhusan, S.; Brandstadt, K.F.; Lane, T.H.; Gross, R.A. "Sweet Silicones": Biocatalytic Reactions to Form Organosilicon Carbohydrate Macromers Org. Lett., 2005, 18, 3857-3860.
191. Poojari, Y.; Clarson, S.J. Lipase catalyzed synthesis of silicone polyesters Chem. Commun., 2009, 6834-6835.
192. Poojari, Y.; Clarson, S.J. Lipase-catalyzed synthesis and properties of silicone aromatic polyesters and silicone aromatic polyamides. Macromolecules, 2010, 43, 4616-4622.
193. 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.
194. Xu, Z.; Zheng, S. Morphology and thermomechanical properties of nanostructured thermosetting blends of epoxy resin and poly(ε-caprolactone)-block-polydimethylsiloxane-block-poly(ε-caprolactone) triblock copolymer. Polymer, 2007, 48, 6134-6144.
195. He, F.; Li, S.; Vert, M.; Zhuo, R. Enzyme-catalyzed polymerization and degradation of copolymers prepared from ε-caprolactone and poly(ethylene glycol). Polymer, 2003, 44, 5145-5151.
196. Poojari, Y.; Clarson, S. J. Lipase catalyzed synthesis of poly(ε-caprolactone)-poly(dimethyl-siloxane)-poly(ε-caprolactone) triblock copolymers Silicon, 2009, 1, 165-172.
197. Park, J.H.; Park, K.D.; Bae, Y.H. PDMS-based polyurethanes with MPEG grafts: synthesis, characterization and platelet adhesion study. Biomaterials, 1999, 20, 943-953.
198. Rutnakornpituk, M.; Ngamdee, P.; Phinyocheep, P. Synthesis, characterization and properties of chitosan modified with poly(ethylene glycol)- polydimethylsiloxane amphiphilic block copolymers. Polymer, 2005, 46, 9742-9752.
199. Poojari, Y.; Clarson, S.J. Lipase catalyzed synthesis and thermal properties of poly(dimethylsiloxane)-poly(ethylene glycol) amphiphilic block copolymers J. Inorg. Organomet. Polym., 2010, 20, 46-52.
200. Coulembier, O.; Degée, P.; Barbaud, C.; Guréin, P.; Dubois, P. Synthesis of amphiphilic poly((R,S)-b-malic acid)-graft-poly(ω-caprolactone): "grafting from" and "grafting through" approaches. Macromolecules, 2005, 38, 3141-3150.
201. Coulembier, O.; Degée, P.; Barbaud, C.; Guréin, P. New amphiphilic graft copolymer based on poly(β-malic acid): synthesis and characterization. Polym. Bull., 2004, 51, 365-372.
202. Zhang, S.; Yang, J.; Liu, X.; Chang, J.; Cao, A. Synthesis and characterization of poly(butylene succinate-co-butylene malate): a new biodegradable copolyester bearing hydroxyl pendant groups. Biomacromolecules, 2003, 4, 437-445.
203. He, B.; Bei, J.; Wang, S. Morphology and degradation of biodegradable poly(l-lactide-co-β-malic acid). Polym. Adv.Tech., 2003, 14, 645-652.
204. Regaño, C.; Alla, A.; Martínez de Ilarduya, A.; Munñoz-Guerra, S. Poly(ester amide)s derived from L-malic acid. Macromolecules, 2004, 37, 2067-2075.
205. He, B.; Cai, Q.; Zhou, X.; Bei, J.; Wang, S. Synthesis and characterization of a functionalized biodegradable copolymer: poly(l-lactide-co-RS-β-malic acid). Polymer, 2003, 44, 989-994.
206. Li, G.; Yao, D.; Zong, M. Lipase-catalyzed synthesis of biodegradable copolymer containing malic acid units in solvent-free system Eur. Polym. J., 2008, 44,1123-1129.
207. Uhrich KE. 2003. Antibiotic polymers. World Patent Appl WO 03/066053 A1, August 14, 2003.
208. Sharma, B.K.; Adhvaryu, A.; Erhan, S.Z. Synthesis of hydroxy thio-ether derivatives of vegetable oil. J. Agric. Food Chem., 2006, 54, 9866-9872.
209. Kato, M.; Toshima, K.; Matsumura, S. Preparation of aliphatic poly (thioester) by the lipase-catalyzed direct polycondensation of 11-mercaptoundecanoic acid. Biomacromolecules, 2005, 6, 2275-2280.
210. Kato, M.; Toshima, K.; Matsumura, S. Enzyme-catalyzed preparation of aliphatic polythioester by direct polycondensation of diacid diester and dithiol. Macromol. Rapid Commun., 2006, 27, 605-610.
211. Weber, N.; Bergander, K.; Fehling, E.; Klein, E.; Vosmann, K.; Mukherjee, K.D. Copolymeric polythioesters by lipase-catalyzed thioesterification and transthioesterification of a,v-alkanedithiols. Appl. Microbiol. Biotechnol., 2006, 70, 290-297.
212. Steinbüchel, A. Non-biodegradable biopolymers from renewable resources: Perspectives and impacts. Curr. Opinion Biotechnol., 2005, 16, 607-613.
213. Kamei, Y.; Nagai, A.; Nishida, H.; Kimura, H.; Endo, T. Biosynthesis and biodegradability of copolythioesters from 3,30-thiodipropionic acid and plant oils by Cupriviadus necator. Macromol. Biosci., 2007, 7, 364-372.
214. Lenz, R.W.; Marchessault, R.H. Bacterial polyesters: Biosynthesis, biodegradable plastics and biotechnology. Biomacromolecules, 2005, 6, 1-8.
215. Tserki, V.; Matzinos, P.; Pavlidou, E.; Vachliotis, D.; Panayiotou, C. Biodegradable aliphatic polyesters. Part I. Properties and biodegradation of poly(butylene succinate-co-butylene adipate). Polymer Degr. Stabil., 2006, 91, 367-376.
216. Jendrossek, D. Microbial degradation of polyesters. Adv. Biochem. Eng. Biotechnol., 2001, 71, 293-325.
217. Tokiwa, Y.; Calabia, B.P. Degradation of microbial polyesters. Biotechnol. Lett., 2004, 26, 1181-1189.
218. Fehling, E.; Klein, E.; Vosmann, K.; Bergander, K.; Weber, N. Linear copolymeric poly(thia-alkanedioates) by lipase-catalyzed esterification and transesterification of 3,3'-thiodipropionic acid and its dimethyl ester with α,ω-alkanediols. Biotechnology and Bioengineering, 2008, 99, 1074-1084.
219. Fehling, E.; Bergander, K.; Klein, E.; Weber, N.; Vosmann, K. Thiolfunctionalized 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.
220. Kato, M.; Toshima, K.; Matsumura, S. Direct Enzymatic synthesis of a polyester with free pendant mercapto groups. Biomacromolecules, 2009, 10, 366-373.
221. Ray, W.C. III; Grinstaff, M.W. Polycarbonate and poly(carbonate-ester)s synthesized from biocompatible building blocks of glycerol and lactic acid. Macromolecules, 2003, 36, 3557-3562.
222. Sanda, F.; Kamatani, J.; Endo, T. Synthesis and anionic ring-opening polymerization behavior of amino acid-derived cyclic carbonates. Macromolecules, 2001, 34, 1564-1569.
223. Al-Azemi, T.F.; Harmon, J.P.; Bisht, K.S. Enzyme-catalyzed ringopening copolymerization of 5-methyl-5-benzyloxycarbonyl-1,3-dioxan-2-one (MBC) with trimethylene carbonate (TMC): synthesis and characterization. Biomacromolecules, 2000, 1, 493-500
224. Al-Azemi, T.F.; Bisht, K.S. One-step synthesis of polycarbonates bearing pendant carboxyl groups by lipase-catalyzed ring-opening polymerization. J. Polym. Sci. Part A: Polym. Chem., 2002, 40, 1267-1274.
225. Lee, R.S.; Yang, J.M.; Lin, T.F. Novel, biodegradable, functional poly(estercarbonate) s by copolymerization of trans-4-hydroxy-L-proline with cyclic carbonate bearing a pendent carboxylic group. J. Polym. Sci., Part A: Polym. Chem., 2004, 42, 2303-2312.
226. Bou, J.J.; Iribarren, I.; Munoz-Guerra, S. Synthesis and properties of stereoregular polyamides derived from L-tartaric acid: poly[(2S,3S)-2,3-dimethoxybutylene alkanamide]s. Macromolecules, 1994, 27, 5263-5270.
227. Mathakiya, I.A.; Rakshit, A.K.; Iyer, B.D.; Shah, A.K. Novel biodegradable polyamides based on tartaric acid: Preparation and properties Int. J. Polym. Mater., 2004, 53, 405-418.
228. Kimura, H.; Yoshinari, T.; Takeishi, M. Synthesis and biodegradation of polyesters based on O-methylene tartaric acid. Polym. J., 1999, 31, 388-392.
229. Villuendas, I.; Iribarren, J.I.; Munoz-Guerra, S. Poly(ester amide)s derived from L-tartaric acid and amino alcohols. 1. Regic polymers. Macromolecules, 1999, 32, 8015-8023.
230. Alia, A.; Rodriguez-Galfin, A.; Martinez de Ilarduya, A.; Munoz-Guerra, S. Degradable poly(ester amide)s based on L-tartaric acid Polymer, 1997, 38, 4935-4944.
231. Acemoglu, M.; Bantle, S.; Mindt, T.; Nimmerfall, F. Novel bioerodible poly(hydroxyalkylene carbonates)s: A versatile class of polymers for medical and pharmaceutical applications. Macromolecules, 1995, 28, 3030-3037.
232. Yokoe, M.; Aoi, K.; Okada, M. Biodegradable polymers based on renewable resources. J. Polym. Sci., Part A: Polym. Chem., 2005, 43, 3909-3919.
233. Wang, X.L.; Zhuo, R.X.; Liu, L.J.; He, F.; Liu, G. Synthesis and characterization of novel aliphatic polycarbonates. J. Polym. Sci., Part A: Polym Chem., 2002, 40, 70-75.
234. Bisht, K.S.; Svirkin, Y.Y.; Henderson, L.A.; Gross, R.A.; Kaplan, D.L.; Swift, G. Lipase-catalyzed ring-opening polymerization of trimethylene carbonate. Macromolecules 1997, 30, 7735-7742
235. Kobayashi, S.; Kikuchi, H.; Uyama, H. Lipase-catalyzed ring-opening polymerization of l,3-dioxan-2-one. Macromol. Rapid Commun., 1997, 18, 575-579.
236. Matsumura, S.; Tsukada, K.; Toshima, K. Enzyme-catalyzed ring-opening polymerization of 1,3-dioxan-2-one to poly(trimethylene carbonate). Macromolecules, 1997, 30, 3122-3124.
237. Feng, J.; Zhuo, R.; He, F.; Wang, X. Synthesis of functional polycarbonates by lipase-catalyzed ring-opening polymerization. Macromol Symp., 2003, 195, 237-240.
238. Lee, R-S.; Yang, Y-M.; Lin, T-F. Novel, biodegradable, functional poly(ester-carbonate)s by copolymerization of trans-4-hydroxy-L-proline with cyclic carbonate bearing a pendent carboxylic group. J. Polym. Sci. Part A: Polym. Chem., 2004, 42, 2303-2312.
239. 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.
240. Kuhling, S.; Keul, H.; Hocker, H. Polymers from 2-allyloxymethyl-2-ethyltrimethylene carbonate and copolymers with 2,2-dimethyltrimethylene carbonate obtained by anionic ring-opening polymerization. Macromol. Chem., 1990, 191, 1611-1622
241. Keul, H.; Bacher, R.; Hocker, H. Macromol. Chem., 1990, 191, 2579-2589.
242. Qiao, L.; Gu, Q.-M.; Cheng, H.N. Enzyme-catalysed synthesis of hydrophobically modified starch. Carbohydr. Polym., 2006, 66, 135-140.
243. Sahoo, S.K.; Nagarajan, R.; Roy, S.; Samuelson, L.A.; Kumar, J.; Cholli, A.L. An enzymatically synthesized polyaniline: A solid-state NMR study. Macromolecules, 2004, 37, 4130-4138.
244. Lee, J.C.; Litt, M.H. Ring-opening polymerization of ethylene carbonate and depolymerization of poly(ethylene oxide-co-ethylene carbonate). Macromolecules, 2000, 33, 1618-1627.
245. Matsuo, J.; Sanda, F.; Endo, T. Cationic ring-opening polymerization behavior of an aliphatic seven-membered cyclic carbonate, 1,3-dioxepan-2-one. Macromol. Chem. Phys., 1998, 199, 97-102
246. Matsuo, J.; Sanda, F.; Endo, T. Anionic ring-opening polymerization behavior of a sevenmembered cyclic carbonate; 1, 3-dioxepan-2-one. J. Polym. Sci., Part A: Polym. Chem., 1997, 35, 1375-1380
247. Matsuo, J.; Sanda, F.; Endo, T. Substituent effect on cationic ring-opening polymerization behavior of seven-membered cyclic carbonates. Macromol. Chem. Phys., 2000, 201, 585-596.
248. Morikawa, H.; Sudo, A.; Nishida, H.; Endo, T. Cationic copolymerization behavior of glycidyl phenyl ether with seven-membered cyclic carbonate. Macromol. Chem. Phys., 2005, 206, 592-599
249. Tomita, H.; Sanda, F.; Endo, T. Polyaddition of bis(seven-membered cyclic carbonate) with diamines: a novel and efficient synthetic method for polyhydroxyurethanes. J. Polym. Sci., Part A: Polym. Chem., 2001, 39, 4091-4100
250. Shibasaki, Y.; Sanda, F.; Endo, T. A novel acid promoted ring-opening polymerization of a sevenmembered cyclic carbonate initiated with BCl3. Macromol. Rapid Commun., 2000, 21, 489-492.
251. Wu, R.; Al-Azemi, T.F.; Bisht, K.S. Functionalized polycarbonate derived from tartaric acid: enzymatic ring-opening polymerization of a sevenmembered cyclic carbonate. Biomacromolecules, 2008, 9, 2921-2928.
252. Feng, J.; Wang, Y-P.; Zhang, X-Z.; Zhuo, R-X. Investigation on lipasecatalyzed solution polymerization of cyclic carbonate. Eur. Polym. J., 2009, 45, 523-529.
253. Rabani, G.; Luftmann, H.; Kraft, A. Synthesis and properties of segmented copolymers containing short aramid hard segments and aliphatic polyester or polycarbonate soft segments. Polymer, 2005, 46, 27-35.
254. Tokiwa, Y. In: Miscellaneous Biopolymers and Biodegradation of Synthetic Polymers; Matsumura, S.; Steinbuechel; A., Eds.; Wiley-VCH:Weinheim, Germany, 2003; pp 417-422.
255. Zhang, Z.; Foks, M.A.; Grijpma, D.W.; Feijen, J. PTMC and MPEG-PTMC microparticles for hydrophilic drug delivery. J. Controlled Release, 2005, 101, 392-394.
256. Tanaka, H.; Kunimura, M. Mechanical properties of thermoplastic polyurethanes containing aliphatic polycarbonate soft segments with different chemical structures. Polym. Eng. Sci., 2002, 42, 1333-1349.
257. Kojio, K.; Nonaka, Y.; Masubuchi, T.; Furukawa, M. Effect of the composition ratio of copolymerized poly(carbonate) glycol on the microphaseseparated structures and mechanical properties of polyurethane elastomers. J. Polym. Sci., Part B: Polym. Phys., 2004, 42, 4448-4458.
258. Matsumura, S.; Harai, S.; Toshima, K. Lipase-catalyzed polymerization of diethyl carbonate and diol to aliphatic poly(alkylene carbonate). Macromol. Chem. Phys., 2000, 201, 1632-1639.
259. Heise, A.; Nijenhuis, A. J.; Schaafsma, A. E. Lipase catalyzed preparation of aliphatic polycarbonates. PCT Int. Appl. WO2005/ 098013 (A1), July 10, 2005.
260. Jiang, Z.; Liu, C.; Xie, W.; Gross, R.A. Controlled lipase-catalyzed synthesis of poly(hexamethylene carbonate). Macromolecules, 2007, 40, 7934-7943.
261. Liu, C.; Jiang, Z.; Decatur, J.; Xie, W.; Gross, R.A. Chain growth and branch structure formation during lipase-catalyzed synthesis of aliphatic polycarbonate polyols. Macromolecules, 2011, 44, 1471-1479.
262. Schaffer, M. A.; McAuley, K. B.; Keith Marchildon, E.; Cunningham, M. F. Thermal degradation kinetics of nylon 6,6. Experimental study and comparison with model predictions. Macromol. React. Eng., 2007, 1, 563-577.
263. Lintner, K.; Gabriele, D. E. Cosmetic or dermopharmaceutical compositions of ceramides and polypeptides. U.S. Patent 2004/0120918 A1, Jun 24, 2004.
264. Haynie, D.T.; Zhao, W. Present and future prospects for polypeptide multilayer nanofilms in biotechnology and medicine. J. Nanosci. Nanotechnol., 2009, 9, 3562-3567.
265. Smith, E.; Shen, J. Surface modifications of wool with protease extracted polypeptides. J. Biotechnol., 2011, 156, 134-140.
266. Vayaboury, W.; Giani, O.; Cottet, H.; Deratani, A.; Schue F. Living polymerization of α-aminoacid-N-carboxyanhydrides (NCA) upon decreasing the reaction temperature. Macromol. Rap. Comm., 2004, 25, 1221-1224.
267. Gu, Q.M.; Maslanka, W. W.; Cheng, H. N. In: Polymer Biocatalysis and Biomaterials II; Cheng, H. N., Gross, R. A., Eds.; ACS Symposium Series: Washington, 2008, 999, Chapter 21, pp 309-319.
268. Schwab, L. W.; Kroon, R.; Schouten, A. J.; Loos, K. Enzyme-Catalyzed Ring-Opening Polymerization of Unsubstituted β-Lactam. Macromol. Rapid Commun. 2008, 29 (10), 794-797.
269. Wilmouth, R.C.; Kassamally, S.; Westwood, N.J.; Sheppard, R.J.; Claridge, T.D.W.; Aplin, R.T. Mechanistic insights into the inhibition of serine proteases by monocyclic lactms. Biochemistry, 1999, 38, 7989-7998.
270. Forró, E.; Fülöp, F. Vapour-assisted enzymatic hydrolysis of β-lactams in a solvent free system. Tetrahedron:Asymmetry, 2008, 19, 1005-1009.
271. Baum, I.; Elsässer, B.; Schwab, L.W.; Loos, K.; Fels, G. Atomistic model for the polyamide formation from β-lactam catalyzed by Candida antarctica lipase B. ACS Catal., 2011, 1, 323-336.
272. Gotor, V. Non-conventional hydrolase chemistry: amide and carbamate bond formation catalyzed by lipases. Bioorg. Med. Chem., 1999, 7, 2189-2197.
273. Baldessari, A.; Mangone, C.P. One-pot biocatalyzed preparation of substituted amides as intermediates of pharmaceuticals. J. Mol. Catal. B: Enzym., 2001, 11, 335-341.
274. Rustoy, E.M.; Baldessari, A. An efficient chemoenzymatic synthesis of the bactericide lapyrium chloride. Eur. J. Org. Chem., 2005, 4628-4632.
275. Rustoy, E.M.; Baldessari A. Chemoselective enzymatic preparation of Nhydroxyalkylacrylamides, monomers for hydrophilic polymer matrices. J. Mol. Catal. B: Enzym., 2006, 39, 50-54.
276. Monsalve, L.N.; Rustoy, E.M.; Baldessari, A. Biocatalytic synthesis of chiral N-(2-hydroxyalkyl)-acrylamides. Biocatal. Biotransform., 2011, 29, 87-95.
277. Monsalve, L.N.; Gillanders, F.; Baldessari, A. Promiscuous Behavior of Rhizomucor miehei lipase in the synthesis of N-substituted β-Amino Esters. Eur. J. Org. Chem., 2012, 1164-1170.
278. Koskinen, A. M. P.; Klibanov, A. M. Enzymatic reactions in organic media, 1st Edition, Chapman & Hall: London, 1996.
279. Cooper, S.J.; Atkins, E.D.T.; Hill, M.J. Temperature induced changes in lamellar crystals of monodisperse nylon 6 and nylon 66 oligoamides. Macromolecules, 1998, 31, 8947-8956.
280. Cheng, H.N.; Maslanka, W.W.; Gu, Q.M. Enzyme-catalyzed polyamides and compositions and processes of preparing and using the same. U.S. Patent 2004/6677427 B1, Jan 13, 2004.
281. Ragupathya, L.; Zienerb, U.; Dyllick-Brenzingerc, R.; von Vacanoc, B.; Landfestera, 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.
282. Tang, L.; Sheu, M. S.; Chu, T.; Huang, Y. H. Anti-inflammatory properties of triblock siloxane copolymer-blended materials. Biomaterials, 1999, 20, 1365-1370.
283. Haupt, M.; Knaus, S.; Rohr, T.; Grubber H. Carbohydrate modified polydimethylsiloxanes. Part 1. J. Macromol. Sci., Pure Appl. Chem., 2000, A37, 323-341.
284. Myiata, T.; Nakamae, K. Polymers with pendant saccharides: Glycopolymers. Trends Polym. Sci., 1997, 5, 198-206.
285. Jadhav, J.Y.; Krigbaum, W.R.; Preston, J. Novel phenyl-substituted aromatic polyamides. Macromolecules, 1988, 21, 538-540.
286. Brandstadt, K. F.; Lane, T. H.; Gross, R. A. Enzyme catalyzed organosilicon esters and amides. US Patent 2004/0082024 A1, April 29, 2004.
287. Palsule, A.S.; Poojari, Y. Enzymatic synthesis of silicone fluorinated aliphatic polyesteramides. Polymer, 2010, 51, 6161-6167.
288. Martimprey, H.D.; Vauthier, C.; Malvy, C.; Couvreur, P. Polymer nanocarriers for the delivery of small fragments of nucleic acids: Oligonucleotides and siRNA. Eur. J. Pharm. Biopharm., 2009, 71, 490-504.
289. Pack, D.W.; Hoffman, A.S.; Pun, S.; Stayton, P.S. Design and development of polymers for gene delivery. Nat. Rev. Drug Discov., 2005, 4, 581-593.
290. Green, J.J.; Langer, R.; Anderson D.G. A combinatorial polymer library approach yields insight into nonviral gene delivery. Acc. Chem. Res., 2008, 41, 749-759.
291. Martino, L.; Scandola, M.; Jiang, Z. Enzymatic synthesis, thermal and crystalline properties of a poly(β-amino ester) and poly(lactone-co-β-amino ester) copolymers. Polymer, 2012, 53,1839-1848.
292. Jensen, K.D.; Nori, A.; Tijerina, M.; Kopečková, P.; Kopeček J. Cytoplasmic delivery and nuclear targeting of synthetic macromolecules. J. Controlled Release, 2003, 87, 89-105.
293. Candau, F.; Selb, J. Hydrophobically modified polyacrylamides prepared by micellar polymerization. Adv. Colloid Interface Sci., 1999, 79,149-172.
294. Sumerlin, B.S.; Lowe, A.B.; Thomas, D.B.; McCormick, C.L. Aqueous solution properties of pH-responsive AB diblock acrylamido copolymers synthesized via aqueous RAFT. Macromolecules, 2003, 36, 5982-5987.
295. Rustoy, E.M.; Sato, Y.; Nonami, H.; Erra-Balsells, R.; Baldessari, A. Lipasecatalyzed synthesis and characterization of copolymers from ethyl acrylate as the only monomer starting material. Polymer, 2007, 48, 1517-1525.
296. Ghan, R.; Shutava, T.; Patel, A.; John, V.T.; Lvov, Y. Enzyme-catalyzed polymerization of phenols within polyelectrolyte microcapsules. Macromolecules, 2004, 37, 4519-4524.
297. Singh, A.; Kaplan D.L. In Vitro Enzyme-Induced Vinyl Polymerization. In: Enzyme-catalyzed synthesis of polymers, Advances in Polymer Science Series, Vol. 194, Springer-Verlag: Berlin, 2006; pp. 211-224.
298. Kalra, B.; Gross, R.A. Horseradish peroxidase mediated free radical polymerization of methyl methacrylate. Biomacromolecules, 2000, 1, 501-505.
299. Kurtoglu, Y.E.; Mishra, M.K.; Kannan, S.; Kannan, R.M. Drug release characateristics of PANAM dendrimer-drug conjugates with different linkers. Int. J. Pharm., 2010, 384,189-194.
300. Svenson, S. Dendrimers as versatile platform in drug delivery applications. Eur J. Pharm. Biopharm., 2009, 71, 445-462.
301. Yiyun, Ch.; Tongwen, X. Polyamidoamine dendrimers used as solubility enhancers of ketoprofen. Eur. J. Med. Chem., 2005, 40, 1188-1192.
302. Börner, H.G. Strategies exploiting functions and self-assembly properties of bioconjugates for polymer material sciences. Prog. Polym. Sci., 2009, 34, 811-851.
303. Harmann, L.; Krause, E.; Antonietti, M.; Börner, H.G. Solid-phase supported polymer synthesis of sequence-defined, multifunctional poly(amidoamines). Biomacromolecules, 2006, 7, 1239-1244.
304. Monsalve, L.N.; Fatema, M.K.; Nonami, H.; Erra-Balsells, R.; Baldessari, A. Lipase-catalyzed synthesis of a novel linear polyamidoamine oligomer. Polymer, 2010, 51, 2998-3005.
305. Acetti, D.; Brenna, E.; Fuganti, C.; Gatti, F.G.; Serra, S. Lipase-catalysed synthesis of homotartaric acid enantiomers. Tetrahedron Lett., 2009, 50, 2249-2251.
306. Rustoy, E.M.; Pereyra, E.N.; Moreno, S.; Baldessari, A. Combination strategy using pure enzymes and whole cells as biocatalysts for the preparation of 2-hydroxyesters and lactones from 2-oxoglutaric acid. Tetrahedron: Asymmetry, 2004, 15, 3763-3768.
307. Quintana, P.; Sandoval, G.; Baldessari, A. Lipase-catalyzed synthesis of medium-and long-chain diesters of 2-oxoglutaric acid. Biocatal. Biotransform., 2011, 29, 1-6.
308. Ladmiral, V.; Melia, E.; Haddleton, D.M. Synthetic glycomers: an overview. Eur. Polym. J., 2004, 40, 431-449.
309. Park, O.J.; Kim, D.Y.; Dordick, J.S. Enzyme-catalyzed synthesis of sugarcontaining monomers and linear polymers. Biotechnol. Bioeng., 2000, 70, 208-216.
310. Pérez-Victoria, I.; Morales, J.C. One-and two-step enzymatic synthesis of polymerizable vinyladipoyl mono-and diesters of non-reducing trisaccharides. J. Mol. Catal. B: Enzym., 2007, 48, 8-15.
311. Moen, A.R.; Ruud, K.; Anthonsen, T. Combination of stereospecific dihydroxylation and enzyme catalyzed enantioselective resolution for synthesis of enantiopure vicinal diols. J. Mol. Catal. B: Enzym., 2008, 50, 74-79.
312. Jakob, F.; Schneider, C. Enzyme-catalyzed kinetic resolution of 1,3-anti-diol monoesters. Efficient preparation of enantiomerically highly enriched and unsymmetrically substituted 1,3-anti-Diols. Eur. J. Org. Chem., 2007, 2958-2963.
313. Patil, D.; Dev, B.; Nag, A. Lipase-catalyzed synthesis of 4-methoxy cinnamoyl glycerol. J. Mol. Catal. B: Enzym., 2011, 73, 5-8.
314. Remaut, K.; Symens, N.; Lucas, B.; Demeester, J.; DeSmedt, S.C. Efficient delivery of intact phosphodiester oligonucleotides by poly-beta-aminoesters. J. Controlled Release, 2010, 144, 65-74.
315. Twaites, B.R.; Alarcon, C.D.; Cunliffe, D.; Lavigne, M.; Pennadam, S.; Smith, J.R.; Gorecki, D.C.; Alexander, C. Thermo and pH responsive polymers as gene delivery vectors: effect of polymer architecture on DNA complexation in vitro. J. Controlled Release, 2004, 97, 551-566.
316. Kurisawa, M.; Yokoyama, M.; Okano, T. Gene expression control by tem-Perature with thermo-responsive polymeric gene carriers. J. Controlled Release, 2000, 69, 127-137
317. Hajjar, A. B.; Nicks, P.F.; Knowles, C.J. Preparation of monomeric acrylic ester intermediates using lipase catalysed transesterifications in organic solvents. Biotechnol. Lett., 1990, 12, 825-830.
318. Popescu, D.; Hoogenboom, R.; Keul, H.; Moeller, M. Hydroxy functional acrylate and methacrylate monomers prepared via lipase-catalyzed transacylation reactions. J. Mol. Catal. B: Enzym., 2010, 62, 81-90.
319. Kim, S. Ch.; Nam, D. Y.; Kim, Y.H.; Song, B.K. Enzymatic acrylation of 2-hydroxy-γ-butyrolactone to synthesize the gamma butyrolactone methacrylate (GBLMA) for photoresist. Biotechnol. Bioprocess Engin., 2010, 15, 208-212.
320. Cavallaro, G.; Pitarresi, G.; Licciardi, M.; Giammona, G. Polymeric prodrug for release of antitumoral agent by specific enzymes. Bioconj. Chem., 2001, 12, 143-151.
321. Cai, X.Q.; Wang, N.; Lin, X.F.The preparation of polymerizable, optically active non-steroidal anti-inflammatory drugs derivatives by irreversible enzymatic methods. J. Mol. Catal. B: Enzym., 2006, 40, 51-57.
322. Athawale, V.; Manjrekar, N.; Athawale, M. Enzymatic synthesis of chiral menthyl methacrylate monomer by Pseudomonas cepacia lipase catalysed resolution of (±)-menthol. J. Mol. Catal. B: Enzym., 2001, 16, 169-173.
323. Wu, Q.; Xia, A.; Lin, X. Synthesis of monosaccharide derivatives and polymeric prodrugs of 5-fluorouridine via two-step enzymatic or chemoenzymatic highly regioselective strategy. J. Mol. Catal. B: Enzym., 2008, 54, 76-82.