Enzymatic Polymerization to Polyesters
Part 3a. Polyesters
Prof. Dr. Shiro Kobayashi,
Dr. Hiroshi Uyama,
Prof. Dr. Shiro Kobayashi
- [email protected]
- +81-75-753-5608 | Fax: +81-75-753-4911
Kyoto University, Department of Materials Chemistry, Graduate School of Engineering, Kyoto, Japan, 606-8501
Search for more papers by this authorDr. Hiroshi Uyama
- [email protected]
- +81-75-753-5638 | Fax: +81-75-753-4911
Kyoto University, Department of Materials Chemistry, Graduate School of Engineering, Kyoto, Japan, 606-8501
Search for more papers by this authorProf. Dr. Shiro Kobayashi,
Dr. Hiroshi Uyama,
Prof. Dr. Shiro Kobayashi
- [email protected]
- +81-75-753-5608 | Fax: +81-75-753-4911
Kyoto University, Department of Materials Chemistry, Graduate School of Engineering, Kyoto, Japan, 606-8501
Search for more papers by this authorDr. Hiroshi Uyama
- [email protected]
- +81-75-753-5638 | Fax: +81-75-753-4911
Kyoto University, Department of Materials Chemistry, Graduate School of Engineering, Kyoto, Japan, 606-8501
Search for more papers by this authorAbstract
- Introduction
- Historical Outline
- Ring-opening Polymerization of Cyclic Monomers
- Polymerization of Lactones
- Polymerization of Other Cyclic Monomers
- Copolymerization of Cyclic Monomers
- Single-step Synthesis of End-functionalized Polyesters
- Polymerization of Dicarboxylic Acid Derivatives and Glycols
- Polyester Synthesis from Dicarboxylic Acids
- Polyester Synthesis from Dicarboxylic Acid Esters
- Polyester Synthesis from Acid Anhydride Derivatives
- Polycarbonate Synthesis by Enzymatic Polycondensation
- Polycondensation of Hydroxyacid Derivatives
- Lipase-catalyzed Modification of Polymers
- Relevant Patents
- Outlook and Perspectives
References
- Abramowicz, D. A., Keese, C. R. (1989) Enzymatic tranesterifications of carbonates in water-restricted environments, Biotechnol. Bioeng. 33, 149–156.
- Al-Azemi, T. F., Bisht, K. S. (1999) Novel functional polycarbonate by lipase-catalyzed ring-opening polymerization of 5-methyl-5-benzyloxycarbonyl-1,3-dioxan-2-one, Macromolecules 32, 6536–6540.
- Al-Azemi, T. F., Bisht, K. S. (2000) Enzyme-catalyzed ring-opening copolymerization of 5-methyl-5-benzyloxycarbonyl-1,3-dioxan-2-one (MBC) with trimethylene carbonate (TMC): synthesis and characterization, Biomacromolecules 1, 493–500.
- Athawale, V. D., Gaonkar, S. R. (1994) Enzymatic synthesis of polyesters by lipase catalyzed polytransesterification, Biotechnol. Lett. 16, 149–154.
- Berkane, C., Mezoul, G., Lalot, T., Brigodiot, M., Maréchal, E. (1997) Lipase-catalyzed polyester synthesis in organic medium. study of ring-chain equilibrium, Macromolecules 30, 7729–7734.
- Binns, F., Roberts, S. M., Taylor, A., Williams, C. F. (1993) Enzymatic polymerization of an unactivated diol/diacid system, J. Chem. Soc.: Perkin Trans 1, 899–904.
-
Binns, F.,
Harffey, P.,
Roberts, S. M.,
Taylor, A.
(1998)
Studies of lipase-catalyzed polyesterification of an unactivated diacid/diol system,
J. Polym. Sci.: Polym. Chem. Ed. 36,
2069–2080.
10.1002/(SICI)1099-0518(19980915)36:12<2069::AID-POLA13>3.0.CO;2-4 CAS Web of Science® Google Scholar
- Binns, F., Harffey, P., Roberts, S. M., Taylor, A. (1999) Studies leading to the large scale synthesis of polyesters using enzymes, J. Chem. Soc.: Perkin Trans 1, 2671–2676.
- Bisht, K. S., Henderson, L. A., Gross, R. A., Kaplan, D. L., Swift, G. (1997a) Enzyme-catalyzed ring-opening polymerization of ω-pentadecalactone, Macromolecules 30, 2705–2711.
- Bisht, K. S., Svirkin, Y. Y., Henderson, L. A., Gross, R. A., Kaplan, D. L., Swift, G. (1997b) Lipase-catalyzed ring-opening polymerization of trimethylene carbonate, Macromolecules 30, 7735–7742.
- Bisht, K. S., Deng, F., Gross, R. A., Kaplan, D. L., Swift, G. (1998) Ethyl glucoside as a multifunctional initiator for enzyme-catalyzed regioselective lactone ring-opening polymerization, J. Am. Chem. Soc. 120, 1363–1367.
- Brazwell, E. M., Filos, D. Y., Morrow, C. J. (1995) 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.: Polym. Chem. Ed. 33, 89–95.
- Bruno, F. F., Akkara, J. A., Ayyagari, M., Kaplan, D. L., Gross, R., Swift, G., Dordick, J. S. (1995) Enzymatic modification of insoluble amylose in organic solvents, Macromolecules 28, 8881–8883.
- Chaudhary, A. K., Beckman, E. J., Russell, A. J. (1995) Rational control of polymer molecular weight and dispersity during enzyme-catalyzed polyester synthesis in supercritical fluids, J. Am. Chem. Soc. 117, 3728–3733.
- Chaudhary, A. K., Lopez, J., Beckman, E. J., Russell, A. J. (1997a) Biocatalytic solvent-free polymerization to produce high molecular polyesters, Biotechnol. Prog. 13, 318–325.
-
Chaudhary, A. K.,
Beckman, E. J.,
Russell, A. J.
(1997b)
Biocatalytic polyester synthesis: analysis of the evolution of molecular weight and end group functionality,
Biotechnol. Bioeng. 55,
227–239.
10.1002/(SICI)1097-0290(19970705)55:1<227::AID-BIT23>3.0.CO;2-H CAS PubMed Web of Science® Google Scholar
- Chaudhary, A. K., Beckman, E. J., Russell, A. J. (1998) Nonequal reactivity model for biocatalytic polytransesterification, AIChE J. 44, 753–764.
- Córdova, A., Iversen, T., Hult, K. (1998a) Lipase-catalyzed synthesis of methyl 6-O-poly(ɛ-caprolactone)glycopyranosides, Macromolecules 31, 1040–1045.
- Córdova, A., Hult, A., Hult, K., Ihre, H., Iversen, T., Malmström, E. (1998b) Synthesis of a poly(ɛ-caprolactone) monosubstituted first generation dendrimer by lipase catalysis, J. Am. Chem. Soc. 120, 13521–13522.
- Córdova, A., Iversen, T., Hult, K., Martinelle, M. (1998c) Lipase-catalyzed formation of macrocycles by ring-opening polymerization of ɛ-caprolactone, Polymer 39, 6519–6524.
- Córdova, A., Iversen, T., Hult, K. (1999) Lipase-catalyzed formation of end-functionalized poly(ɛ-caprolactone) by initiation and termination reactions, Polymer 40, 6709–6721.
- Deng, F., Gross, R. A. (1999) Ring-opening bulk polymerization of ɛ-caprolactone and trimethylene carbonate catalyzed by lipase Novozym 435, Int. J. Biol. Macromol. 25, 153–159.
- Dong, H., Wang, H.-D., Cao, S.-G., Shen, J.-C. (1998) Lipase-catalyzed polymerization of lactones and linear hydroxyesters, Biotechnol. Lett. 20, 905–908.
- Ebata, H., Toshima, K., Matsumura, S. (2000) Lipase-catalyzed transformation of poly(ɛ-caprolactone) into cyclic dicaprolactone, Biomacromolecules 1, 511–514.
- Feng, Y., Knüfermann, J., Klee, D., Höcker, H. (1999) Enzyme-catalyzed ring-opening polymerization of 3(S)-isopropylmorpholine-2,5-dione, Macromol. Rapid Commun. 20, 88–90.
- Feng, Y., Klee, D., Keul, H., Höcker, H. (2000) Lipase-catalyzed ring-opening polymerization of morpholine-2,5-dione derivatives: a novel route to the synthesis of poly(ester amide)s, Macromol. Chem. Phys. 201, 2670–2675.
- Geresh, S., Gilboa, Y. (1990) Enzymatic synthesis of alkyds, Biotechnol. Bioeng. 36, 270–274.
- Geresh, S., Gilboa, Y. (1991) Enzymatic synthesis of alkyds. II. Lipase-catalyzed polytransesterification of dichloroethyl fumarate with aliphatic and aromatic diols, Biotechnol. Bioeng. 37, 883–888.
- Gross, R. A., Kaplan, D. L., Swift, G. (Eds.) (1998) Enzymes in Polymer Syntheses ( ACS Symp. Ser. 684). Washington, DC: American Chemical Society.
- Jarvie, A. W. P., Overton, N., St Pourcain, C. B. (1998) Enzymatic epoxidation of polybutadiene, J. Chem. Soc., Chem. Commun. 177–178.
- Jones, J. B. (1986) Enzymes in organic synthesis, Tetrahedron 42, 3351–3403.
- Joo, H., Yoo, Y. J., Dordick, J. S. (1998) Polymers from biocatalysts, Korean J. Chem. Eng. 15, 362–374.
- Kikuchi, H., Uyama, H., Kobayashi, S. (2000) Lipase-catalyzed enantioselective copolymerization of substituted lactones to optically active polyesters, Macromolecules 33, 8971–8975.
- Klibanov, A. M. (1990) Asymmetric transformations catalyzed by enzymes in organic solvents, Acc. Chem. Res. 23, 114–120.
- Kline, B. J., Beckman, E. J., Russell, A. J. (1998) One-step biocatalytic synthesis of linear polyesters with pendant hydroxyl groups, J. Am. Chem. Soc. 120, 9475–9480.
-
Kline, B. J.,
Lele, S. S.,
Lenart, P. J.,
Beckman, E. J.,
Russell, A. J.
(2000)
Use of a batch-stirred reactor to rationally tailor biocatalytic polytransesterification,
Biotechnol. Bioeng. 67,
424–434.
10.1002/(SICI)1097-0290(20000220)67:4<424::AID-BIT6>3.0.CO;2-4 CAS PubMed Web of Science® Google Scholar
- Knani, D., Gutman, A. L., Kohn, D. H. (1993) Enzymatic polyesterification in organic media. Enzyme-catalyzed synthesis of linear polyesters. I. Condensation polymerization of linear hydroxyesters. II. Ring-opening polymerization of ɛ-caprolactone, J. Polym. Chem.: Polym. Chem. Ed. 31, 1221–1232.
- Knani, D., Kohn, D. H. (1993) Enzymatic polyesterification in organic media. II. Enzyme-catalyzed synthesis of lateral-substituted aliphatic polyesters and copolyesters, J. Polym. Sci.: Polym. Chem. Ed. 31, 2887–2897.
-
Kobayashi, S.
(1999)
Enzymatic polymerization: a new method of polymer synthesis,
J. Polym. Chem.: Polym. Chem. Ed. 37,
3041–3056.
10.1002/(SICI)1099-0518(19990815)37:16<3041::AID-POLA1>3.0.CO;2-V CAS Web of Science® Google Scholar
- Kobayashi, S., Uyama, H. (1993) Enzymatic polymerization of cyclic acid anhydride and glycols by a lipase catalyst, Makromol. Chem.: Rapid Commun. 14, 841–844.
- Kobayashi, S., Uyama, H. (1994) Recent advances of macromonomer synthesis and its application, in: Macromolecular Design: Concept and Practice ( M. K. Mishra, Ed.), New York: Polymer Frontiers International, 1–38.
-
Kobayashi, S.,
Uyama, H.
(1998)
Biocatalytical routes to polymers, in: Materials Science and Technology – Synthesis of Polymers ( R. W. Cahn, P. Haasen, E. J. Kramer, Eds.), Weinheim, Germany: Wiley-VCH,
549–569.
10.1002/9783527619313.ch16 Google Scholar
- Kobayashi, S., Uyama, H. (1999) Precision enzymatic polymerization to polyesters with lipase catalysts, Macromol. Symp. 144, 237–246.
-
Kobayashi, S.,
Uyama, H.
(2001a)
In vitro biosynthesis of polyesters, in: Biopolyesters ( W. Babel, A. Steinbüchel, Eds.), Heidelberg: Springer-Verlag,
241–262.
10.1007/3-540-40021-4_8 Google Scholar
- Kobayashi, S., Uyama, H. (2001b) Enzymatic polymerization, in: Encyclopedia of Polymer Science and Technology, 3rd Edn (Kroschwitz, J. I., Ed.) New York: John Wiley & Sons, in press.
- Kobayashi, S., Shoda, S., Uyama, H. (1995) Enzymatic polymerization and oligomerization, Adv. Polym. Sci. 121, 1–30.
- Kobayashi, S., Shoda, S., Uyama, H. (1996) Enzyme-catalyzed polymerization, in: The Polymeric Materials Encyclopedia ( J. C. Salamone, Ed.), Boca Raton, FL: CRC Press, 2102–2107.
- Kobayashi, S., Kikuchi, H., Uyama, H. (1997a) Lipase-catalyzed ring-opening polymerization of 1,3-dioxan-2-one, Macromol. Rapid Commun. 18, 575–579.
- Kobayashi, S., Shoda, S., Uyama, H. (1997b) Enzyme catalysis, in: Catalysis in Precision Polymerization ( S. Kobayashi, Ed.), Chichester: John Wiley & Sons, 417–441.
- Kobayashi, S., Uyama, H., Suda, S., Namekawa, S. (1997c) Dehydration polymerization in aqueous medium catalyzed by lipase, Chem. Lett. 105.
-
Kobayashi, S.,
Takeya, K.,
Suda, S.,
Uyama, H.
(1998a)
Lipase-catalyzed ring-opening polymerization of medium-size lactones to polyesters,
Macromol. Chem. Phys. 199,
1729–1736.
10.1002/(SICI)1521-3935(19980801)199:8<1729::AID-MACP1729>3.0.CO;2-V CAS Web of Science® Google Scholar
- Kobayashi, S., Uyama, H., Namekawa, S. (1998b) In vitro biosynthesis of polyesters with isolated enzymes in aqueous systems and organic solvents, Polym. Degrad. Stab. 59, 195–201.
- Kobayashi, S., Uyama, H., Namekawa, S., Hayakawa, H. (1998c) Enzymatic ring-opening polymerization and copolymerization of 8-octanolide by lipase catalyst, Macromolecules 31, 5655–5659.
- Kobayashi, S., Uyama, H., Takamoto, T. (2000) Lipase-catalyzed degradation of polyesters in organic solvents: a new methodology of polymer recycling using enzyme as catalyst, Biomacromolecules 1, 3–5.
- Kobayashi, S., Uyama, H., Ohmae, M. (2001) Enzymatic polymerization for precision polymer synthesis, Bull. Chem. Soc. Jpn. 74, 613–635.
-
Küllmer, K.,
Kikuchi, H.,
Uyama, H.,
Kobayashi, S.
(1998)
Lipase-catalyzed ring-opening polymerization of α-methyl-δ-valerolactone and α-methyl-ɛ-caprolactone,
Macromol. Rapid Commun. 19,
127–130.
10.1002/(SICI)1521-3927(19980201)19:2<127::AID-MARC127>3.0.CO;2-3 CAS Web of Science® Google Scholar
- Kumar, A., Gross, R. A. (2000a) Candida antarctica lipase B catalyzed polycaprolactone synthesis: effects of organic media and temperature, Biomacromolecules 1, 133–138.
- Kumar, A., Gross, R. A. (2000b) Candida antarctica lipase B-catalyzed transesterification: new synthetic routes to copolyesters, J. Am. Chem. Soc. 122, 11767–11770.
- Kumar, A., Gross, R. A., Jendrossek, D. (2000a) Poly(3-hydroxybutyrate)-depolymerase from Pseudomonas lemoignei: catalysis of esterifications in organic media, J. Org. Chem. 65, 7800–7806.
- Kumar, A., Kalra, B., Dekhterman, A., Gross, R. A. (2000b) Efficient ring-opening polymerization and copolymerization of ɛ-caprolactone and ω-pentadecalactone catalyzed by Candida antarctica lipase B, Macromolecules 33, 6303–6309.
- Kumar, G. S., Ghogare, A., Mukesh, D. (1997) Synthesis of alkyds involving regioselective lipase-catalyzed transesterification in organic media, J. Appl. Polym. Sci. 63, 35–45.
- Lalot, T., Brigodiot, M., Maréchal, E. (1991) Lipozyme-catalyzed transesterification of oligo(methyl methacrylate)s, Polym. Bull. 26, 55–62.
- Li, J., Xie, W., Cheng, H. N., Nickol, R. G., Wang, P. G. (1999) Polycaprolactone-modified hydroxyethylcellulose films prepared by lipase-catalyzed ring-opening polymerization, Macromolecules 32, 2789–2792.
- Linko, Y.-Y., Wang, Z.-L., Seppälä, J. (1994) Lipase-catalyzed synthesis of poly(1,4-butanediol succinate) in organic solvent, Biocatalysis 8, 269–282.
- Linko, Y.-Y., Wang, Z.-L., Seppälä, J. (1995a) Lipase-catalyzed linear aliphatic polyester synthesis in organic solvent, Enzyme Microb. Technol. 17, 506–511.
- Linko, Y.-Y., Wang, Z.-L., Seppälä, J. (1995b) Lipase-catalyzed synthesis of poly(1,4-butyl sebacate) from sebacic acid or its derivatives with 1,4-butanediol, J. Biotechnol. 40, 133–138.
- Linko, Y.-Y., Seppälä, J. (1996) Producing high molecular weight biodegradable polyesters, CHEMTECH 26(8), 25–31.
- MacDonald, R. T., Pulapura, S. K., Svirkin, Y. Y., Gross, R. A., Kaplan, D. L., Akkara, J., Swift, G., Wolk, S. (1995) Enzyme-catalyzed ɛ-caprolactone ring-opening polymerization, Macromolecules 28, 73–78.
- Matsumura, S., Beppu, H., Nakamura, K., Osanai, S., Toshima, K. (1996a) Preparation of poly(β-malic acid) by enzymatic polymerization of benzyl β-malolactonate, Chem. Lett. 795–796.
- Matsumura, S., Beppu, H., Tsukada, K., Toshima, K. (1996b) Enzyme-catalyzed ring-opening polymerization of β-propiolactone, Biotechnol. Lett. 18, 1041–1046.
- Matsumura, S., Mabuchi, K., Toshima, K. (1997a) Lipase-catalyzed ring-opening polymerization of lactide, Macromol. Rapid Commun. 18, 477–482.
- Matsumura, S., Tsukada, K., Toshima, K. (1997b) Enzyme-catalyzed ring-opening polymerization of 1,3-dioxan-2-one to poly(trimethylene carbonate), Macromolecules 30, 3122–3124.
- Matsumura, S., Mabuchi, K., Toshima, K. (1998a) Novel ring-opening polymerization of lactide by lipase, Macromol. Symp. 130, 285–304.
-
Matsumura, S.,
Okamoto, T.,
Tsukada, K.,
Toshima, K.
(1998b)
Novel lipase-catalyzed ring-opening copolymerization of oxiranes and succinic anhydride forming polyesters bearing functional groups,
Macromol. Rapid Commun. 19,
295–298.
10.1002/(SICI)1521-3927(19980601)19:6<295::AID-MARC295>3.0.CO;2-0 CAS Web of Science® Google Scholar
- Matsumura, S., Suzuki, Y., Tsukada, K., Toshima, K., Doi, Y., Kasuya, K. (1998c) Lipase-catalyzed ring-opening polymerization of β-butyrolactone to the cyclic and linear poly(3-hydroxybutyrate), Macromolecules 31, 6444–6449.
- Matsumura, S., Beppu, H., Toshima, K. (1999a) Enzymatic preparation of malate-based polycarboxylates having higher molecular weights by copolymerization with lactone, Chem. Lett. 249–250.
- Matsumura, S., Harai, S., Toshima, K. (1999b) Enzymatic synthesis of poly(tetramethylene carbonate) from diethyl carbonate and 1,4-butanediol, Proc. Jpn. Acad. 75B, 117–121.
- Matsumura, S., Okamoto, T., Tsukada, K., Mizutani, N., Toshima, K. (1999c) Novel lipase-catalyzed ring-opening copolymerization of oxiranes and dicarboxylic anhydride forming polyesters bearing carboxyl groups and their physicochemical properties and biodegradability, Macromol. Symp. 144, 219–235.
- Matsumura, S., Tsukada, K., Toshima, K. (1999d) Novel lipase-catalyzed ring-opening copolymerization of lactide and trimethylene carbonate forming poly(ester carbonate)s, Int. J. Biol. Macromol. 25, 161–167.
- Matsumura, S., Ebata, H., Toshima, K. (2000a) A new strategy for sustainable polymer recycling using an enzyme: poly(ɛ-caprolactone), Macromol. Rapid Commun. 21, 860–863.
- Matsumura, S., Harai, S., Toshima, K. (2000b) Lipase-catalyzed polymerization of diethyl carbonate and diol to aliphatic poly(alkylene carbonate), Macromol. Chem. Phys. 201, 1632–1639.
- Mesiano, A. J., Beckman, E. J., Russell, A. J. (2000) Biocatalytic synthesis of fluorinated polyesters, Biotechnol. Prog. 16, 64–68.
- Mezoul, G., Lalot, T., Brigodiot, M., Maréchal, E. (1995a) Enzyme-catalyzed synthesis of aliphatic polyesters in organic media: study of transesterification equilibrium shift and characterization of cyclic compounds, J. Polym. Sci.: Polym. Chem. Ed. 33, 2691–2698.
- Mezoul, G., Lalot, T., Brigodiot, M., Maréchal, E. (1995b) Enzyme-catalyzed syntheses of poly(1,6-hexanediyl maleate) and poly(1,6-hexanediyl fumarate) in organic medium, Macromol. Rapid Commun. 16, 613–620.
- Mezoul, G., Lalot, T., Brigodiot, M., Maréchal, E. (1996a) Enzyme-catalyzed syntheses of poly(1,6-hexanediyl isophthalate) and poly(1,6-hexanediyl terephthalate) in organic medium, Polym. Bull. 36, 541–548.
- Mezoul, G., Lalot, T., Brigodiot, M., Maréchal, E. (1996b) Enzyme-catalyzed synthesis of poly(1,6-hexanediyl maleate-co-fumarate) in organic medium. Study of macrolactone formation in relation to the composition of the initial monomer mixture, Macromol. Chem. Phys. 197, 3581–3592.
- Mohanty, A. K., Misra, M., Hinrichsen, G. (2000) Biofibres, biodegradable polymers and biocomposites: an overview, Macromol. Mater. Eng. 276/277, 1–24.
- Müller, S., Uyama, H., Kobayashi, S. (1999) Lipase-catalyzed ring-opening polymerization of cyclic diesters, Chem. Lett. 1317–1318.
- Namekawa, S., Uyama, H., Kobayashi, S. (1996) Lipase-catalyzed ring-opening polymerization and copolymerization of β-propiolactone, Polym. J. 28, 730–731.
- Namekawa, S., Uyama, H., Kobayashi, S. (1998a) Lipase-catalyzed ring-opening polymerization of lactones in water, Polym. J. 30, 269–271.
- Namekawa, S., Uyama, H., Kobayashi, S. (1998b) Lipase-catalyzed ring-opening polymerization of 16-hexadecanolide, Proc. Jpn. Acad. 74B, 65–68.
- Namekawa, S., Suda, S., Uyama, H., Kobayashi, S. (1999) Lipase-catalyzed ring-opening polymerization of lactones to polyesters and its mechanistic aspects, Int. J. Biol. Macromol. 25, 145–151.
- Namekawa, S., Uyama, H., Kobayashi, S. (2000a) Enzymatic synthesis of polyesters from lactones, dicarboxylic acid divinyl esters, and glycols through combination of ring-opening polymerization and polycondensation, Biomacromolecules 1, 335–338.
-
Namekawa, S.,
Uyama, H.,
Kobayashi, S.,
Kricheldorf, H. R.
(2000b)
Lipase-catalyzed ring-opening polymerization and copolymerization of cyclic dicarbonate,
Macromol. Chem. Phys. 201,
261–264.
10.1002/(SICI)1521-3935(20000201)201:2<261::AID-MACP261>3.0.CO;2-Q CAS Web of Science® Google Scholar
- Namekawa, S., Uyama, H., Kobayashi, S. (2001) Lipase-catalyzed ring-opening polymerization of lactones in the presence of aliphatic polyesters to ester copolymers, Macromol. Chem. Phys. 202, 801–806.
-
Nishida, H.,
Yamashita, M.,
Nagashima, M.,
Endo, T.,
Tokiwa, Y.
(2000)
Synthesis of metal-free poly(1,4-dioxan-2-one) by enzyme-catalyzed ring-opening polymerization,
J. Polym. Sci.: Polym. Chem. Ed. 38,
1560–1567.
10.1002/(SICI)1099-0518(20000501)38:9<1560::AID-POLA20>3.0.CO;2-F CAS Web of Science® Google Scholar
- Nobes, G. A. R., Kazlauskas, R. J., Marchessault, R. H. (1996) Lipase-catalyzed ring-opening polymerization of lactones: a novel route to poly(hydroxyalkanoate)s, Macromolecules 29, 4829–4833.
- Noda, S., Kamiya, N., Goto, M., Nakashio, F. (1997) Enzymatic polymerization catalyzed by surfactant-coated lipases in organic media, Biotechnol. Lett. 19, 307–309.
- Noll, O., Ritter, H. (1996) Enzymes in polymer chemistry, 9. Polymerizable oligoesters from cholic acid via lipase catalyzed condensation reactions, Macromol. Rapid Commun. 17, 553–557.
- Noll, O., Ritter, H. (1997) New side-chain poly(methacryl-rotaxanes) bearing cyclodextrins as non-covalently anchored ring components. Chemoenzymatic synthesis and degradation, Macromol. Rapid Commun. 18, 53–58.
- O'Hagan, D., Zaidi, N. A. (1993) Polymerization of 10-hydroxydecanoic acid with the lipase from Candida cyclindracea, J. Chem. Soc.: Perkin Trans 1, 2389–2390.
- O'Hagan, D., Zaidi, N. A. (1994) Enzyme-catalyzed condensation polymerization of 11-hydroxyundecanoic acid with lipase from Candida cylindracea, Polymer 35, 3576–3578.
- O'Hagan, D., Parker, A. H. (1998) Enzyme mediated polyester synthesis with the lipase from Candida rugosa, Polym. Bull. 41, 519–524.
- Osanai, Y., Toshima, K., Matsumura, S. (2000) Lipase-catalyzed reaction of molecularly pure linear and cyclic poly(3-hydroxybutanoate)s: evidence of cyclic polymer formation, Chem. Lett. 576–577.
- Park, O.-J., Kim, D.-Y., Dordick, J. S. (2000) Enzyme-catalyzed synthesis of sugar-containing monomers and polymers, J. Polym. Chem.: Polym. Chem. Ed. 70, 208–216.
- Patil, D. R., Rethwisch, D. G., Dordick, J. S. (1991) Enzymatic synthesis of a sucrose-containing linear polyester in nearly anhydrous organic media, Biotechnol. Bioeng. 37, 639–646.
- Pavel, K., Ritter, H. (1991) Enzymes in polymer chemistry, 5. Radical polymerization of different 11-methacryloylaminoundecanoic acid esters and oligoesters esterified by lipase, Makromol. Chem. 192, 1941–1949.
- Ritter, H. (1997) Functionalized polymers via enzymatic synthesis, in: Desk References of Functional Polymers. Syntheses and Applications ( R. Arshady, Ed.), Washington, DC: American Chemical Society, 103–113.
-
Rodney, R. L.,
Allinson, B. T.,
Beckman, E. J.,
Russell, A. J.
(1999a)
Enzyme-catalyzed polycondensation reactions for the synthesis of aromatic polycarbonates and polyesters,
Biotechnol. Bioeng. 65,
485–489.
10.1002/(SICI)1097-0290(19991120)65:4<485::AID-BIT14>3.0.CO;2-7 CAS PubMed Web of Science® Google Scholar
-
Rodney, R. L.,
Stagno, J. L.,
Beckman, E. J.,
Russell, A. J.
(1999b)
Enzymatic synthesis of carbonate monomers and polycarbonates,
Biotechnol. Bioeng. 62,
259–266.
10.1002/(SICI)1097-0290(19990205)62:3<259::AID-BIT2>3.0.CO;2-I CAS PubMed Web of Science® Google Scholar
-
Runge, M.,
O'Hagan, D.,
Haufe, G.
(2000)
Lipase-catalyzed polymerization of fluorinated lactones and fluorinated hydroxycarboxylic acids,
J. Polym. Sci.: Polym. Chem. Ed. 38,
2004–2012.
10.1002/(SICI)1099-0518(20000601)38:11<2004::AID-POLA90>3.0.CO;2-T CAS Web of Science® Google Scholar
- Santaniello, E., Ferraboschi, P., Grisenti, P., Manzocchi, A. (1992) The biocatalytic approach to the preparation of enantiomerically pure chiral building blocks, Chem. Rev. 92, 1071–1140.
-
Schmid, R. D.,
Verger, R.
(1998)
Lipases: interfacial enzymes with attractive applications,
Angew. Chem. Int. Ed. 37,
1608–1633.
10.1002/(SICI)1521-3773(19980703)37:12<1608::AID-ANIE1608>3.0.CO;2-V CAS PubMed Web of Science® Google Scholar
- Seoane, G. (2000) Enzymatic C–C bond-forming reactions in organic synthesis, Curr. Org. Chem. 4, 283–304.
- Shuai, X., Jedlinski, Z., Kowalczuk, M., Rydz, J., Tan, H. (1999) Enzymatic synthesis of polyesters from hydroxyl acids, Eur. Polym. J. 35, 721–725.
- Suda, S., Uyama, H., Kobayashi, S. (1999) Dehydration polycondensation in water for synthesis of polyesters by lipase catalyst, Proc. Jpn. Acad. 75B, 201–206.
- Suzuki, Y., Ohura, T., Kasuya, K., Toshima, K., Doi, Y., Matsumura, S. (2000) Enzyme-catalyzed ring-opening polymerization of β-butyrolactone using PHB depolymerase, Chem. Lett. 318–319.
- Svirkin, Y. Y., Xu, J., Gross, R. A., Kaplan, D. L., Swift, G. (1996) Enzyme-catalyzed stereoselective ring-opening polymerization of α-methyl-β-propiolactone, Macromolecules 29, 4591–4597.
-
Szakács-Schmidt, A.,
Albert, L.,
Kelemen-Horváth, I.
(1999)
Study of enzyme-catalyzed polymerization of lactic acid by HPLC and MALDI-MS,
Biomed. Chromatogr. 13,
252–253.
10.1002/(SICI)1099-0801(199905)13:3<252::AID-BMC826>3.0.CO;2-X PubMed Web of Science® Google Scholar
- Tsujimoto, T., Uyama, H., Kobayashi, S. (2001) Enzymatic synthesis of crosslinkable polyesters from renewable resources, Biomacromolecules 2, 29–31.
- Uyama, H., Kobayashi, S. (1993) Enzymatic ring-opening polymerization of lactones catalyzed by lipase, Chem. Lett. 1149–1150.
- Uyama, H., Kobayashi, S. (1994) Lipase-catalyzed polymerization of divinyl adipate with glycols to polyesters, Chem. Lett. 1687–1690.
- Uyama, H., Takeya, K., Kobayashi, S. (1993) Synthesis of polyesters by enzymatic ring-opening copolymerization using lipase catalyst, Proc. Jpn. Acad. 69B, 203–207.
- Uyama, H., Kikuchi, H., Kobayashi, S. (1995a) One-shot synthesis of polyester macromonomer by enzymatic ring-opening polymerization of lactone in the presence of vinyl ester, Chem. Lett. 1047–1048.
- Uyama, H., Takeya, K., Kobayashi, S. (1995b) Enzymatic ring-opening polymerization of lactones to polyesters by lipase catalyst: unusually high reactivity of macrolides, Bull. Chem. Soc. Jpn. 68, 56–61.
- Uyama, H., Takeya, K., Hoshi, N., Kobayashi, S. (1995c) Lipase-catalyzed ring-opening polymerization of 12-dodecanolide, Macromolecules 28, 7046–7050.
- Uyama, H., Kikuchi, H., Takeya, K., Hoshi, N., Kobayashi, S. (1996a) Immobilized lipase showing high catalytic activity toward enzymatic ring-opening polymerization of macrolides, Chem. Lett. 107–108.
- Uyama, H., Kikuchi, H., Takeya, K., Kobayashi, S. (1996b) Lipase-catalyzed ring-opening polymerization and copolymerization of 15-pentadecanolide, Acta Polymerica 47, 357–360.
- Uyama, H., Kikuchi, H., Kobayashi, S. (1997a) Single-step acylation of polyester terminals by enzymatic ring-opening polymerization of 12-dodecanolide in the presence of acyclic vinyl esters, Bull. Chem. Soc. Jpn. 70, 1691–1695.
- Uyama, H., Namekawa, S., Kobayashi, S. (1997b) Mechanistic studies on the lipase-catalyzed ring-opening polymerization of lactones, Polym. J. 29, 299–301.
- Uyama, H., Suda, S., Kikuchi, H., Kobayashi, S. (1997c) Extremely efficient catalysis of immobilized lipase in ring-opening polymerization of lactones, Chem. Lett. 1109–1110.
- Uyama, H., Inada, K., Kobayashi, S. (1998a) Enzymatic polymerization of dicarboxylic acid and glycol to polyester in solvent-free system, Chem. Lett. 1285–1286.
- Uyama, H., Suda, S., Kobayashi, S. (1998b) Enzymatic synthesis of terminal-functionalized polyesters by initiator method, Acta Polymerica 49, 700–703.
-
Uyama, H.,
Inada, K.,
Kobayashi, S.
(1999a)
Regioselective polymerization of divinyl sebacate and triols using lipase catalyst,
Macromol. Rapid Commun. 20,
171–174.
10.1002/(SICI)1521-3927(19990401)20:4<171::AID-MARC171>3.0.CO;2-2 CAS Web of Science® Google Scholar
- Uyama, H., Wada, S., Kobayashi, S. (1999b) Synthesis of aliphatic polyester by insertion of glycols into polyanhydrides using lipase catalyst, Chem. Lett. 893–894.
-
Uyama, H.,
Yaguchi, S.,
Kobayashi, S.
(1999c)
Lipase-catalyzed polycondensation of dicarboxylic acid-divinyl esters and glycols to aliphatic polyesters,
J. Polym. Sci.: Polym. Chem. Ed. 37,
2737–2745.
10.1002/(SICI)1099-0518(19990801)37:15<2737::AID-POLA7>3.0.CO;2-M CAS Web of Science® Google Scholar
- Uyama, H., Yaguchi, S., Kobayashi, S. (1999d) Enzymatic synthesis of aromatic polyesters by lipase-catalyzed polymerization of dicarboxylic acid divinyl esters and glycols, Polym. J. 31, 380–383.
- Uyama, H., Ikeda, R., Yaguchi, S., Kobayashi, S. (2000a) Enzymatic polymerization of natural phenol derivatives and enzymatic synthesis of polyesters from vinyl esters, ACS Symp. Ser. 764, 113–127.
- Uyama, H., Inada, K., Kobayashi, S. (2000b) Lipase-catalyzed synthesis of aliphatic polyesters by polycondensation of dicarboxylic acids and glycols in solvent-free system, Polym. J. 32, 440–443.
- Uyama, H., Klegraf, E., Wada, S., Kobayashi, S. (2000c) Regioselective polymerization of sorbitol and divinyl sebacate using lipase catalyst, Chem. Lett. 800–801.
- Uyama, H., Inada, K., Kobayashi, S. (2001) Regioselectivity control in lipase-catalyzed polymerization of divinyl sebacate and triols, Macromol. Biosci. 1, 40–44.
- Wada, S., Uyama, H., Kobayashi, S. (2000) Synthesis of hyperbranched polyesters by enzymatic polymerization, Polym. Prepr., Jpn. 49, 1790–1791.
- Wallace, J. S., Morrow, C. J. (1989a) Biocatalytic synthesis of polymers. synthesis of an optically active, epoxy-substituted polyester by lipase-catalyzed polymerization, J. Polym. Sci.: Polym. Chem. Ed. 27, 2553–2567.
- Wallace, J. S., Morrow, C. J. (1989b) Biocatalytic synthesis of polymers. II. preparation of [AA–BB]x polyesters by porcine pancreatic lipase catalyzed transesterification in anhydrous, low polarity organic solvents, J. Polym. Sci.: Polym. Chem. Ed. 27, 3271–3284.
- Wallace, J. S., Reda, K. B., Williams, M. E., Morrow, C. J. (1990) Resolution of a chiral ester by lipase-catalyzed transesterification with poly(ethylene glycol) in organic media, J. Org. Chem. 55, 3544–3546.
- Wang, Z.-L., Hiltunen, K., Orava, P., Seppälä, J., Linko, Y.-Y. (1996) Lipase-catalyzed polyester synthesis, J. Macromol. Sci.: Pure Appl. Chem. A33, 599–612.
-
Wen, J.,
Zhuo, R.-X.
(1998)
Enzyme-catalyzed ring-opening polymerization of ethylene isopropyl phosphate,
Macromol. Rapid Commun. 19,
641–644.
10.1002/(SICI)1521-3927(19981201)19:12<641::AID-MARC641>3.0.CO;2-I CAS Web of Science® Google Scholar
-
Wong, C.-H.,
Whitesides, G. M.
(1994)
Enzymes in Synthetic Organic Chemistry, Oxford: Pergamon.
10.1016/B978-0-08-035941-0.50005-7 Google Scholar
- Wu, X., Linko, Y.-Y., Seppälä, J. (1998) Lipase biocatalysis in the production of aromatic polyesters, Ann. NY Acad. Sci. 864, 399–404.
- Xie, W., Li, J., Chen, D., Wang, P. G. (1997) Ring-opening polymerization of β-butyrolactone by thermophilic lipases, Macromolecules 30, 6997–6998.
Citing Literature
Biopolymers Online: Biology • Chemistry • Biotechnology • Applications
Browse other articles of this reference work: