Syntezy modelowych polimerów biodegradowalnych z zastosowaniem katalizy enzymatycznej In Vitro

Rydz, J.; Kowalczuk, M.

Artykuł - szczegóły

Tytuł artykułu

Syntezy modelowych polimerów biodegradowalnych z zastosowaniem katalizy enzymatycznej In Vitro

Autorzy

Rydz J. , Kowalczuk M.

Wybrane pełne teksty z tego czasopisma

Identyfikatory

Warianty tytułu

Syntheses of model biodegradable polymers with the aid of enzymatic catalysis in vitro

Języki publikacji

Abstrakty

The use of enzymatic catalysis, in an organic medium, for synthesis of polysaccharides, polyesters, polyaromatics and polypeptides has experienced important developments over past few years. The review deals with recent advances in synthesis of biodegradable polymers, and aliphatic polyesters in particular, via in vitro enzymatic catalysis. Recently, biodegradable aliphatic polyesters have attracted great interest in medicine as well as environmentally acceptable materials for packaging industry and agriculture. The enzyme-catalysed condensation reactions, ring-opening polymerisation, and corresponding transesterification of macromolecular substrates, as tools for their preparation, are discussed. Enzymes in polymer synthesis offer several advantages as substrate selectivity, enantio-, regio- and chemoselectivity. They enable, under mild reaction conditions and in the presence of or without organic solvents (in bulk), creation of useful polymeric materials with elimination of the potentially toxic catalysts. Some of functional polymers, difficult to obtain by conventional methodologies, may be synthesised using enzymes as catalysts. Although enzymatic procedures sometimes are not suitable for a large-scale preparation they can be successfully applied for new synthetic strategies for modelled polymers with desired topology and structure, including structure of the polymer end groups.

Słowa kluczowe

kataliza enzymatyczna polimery biodegradacja

enzymatic catalysis polymers biodegradation

Wydawca

Polskie Towarzystwo Chemiczne

Czasopismo

Wiadomości Chemiczne

Rocznik

2003

Tom

[Z] 57, 1-2

Strony

1--19

Opis fizyczny

Bibliogr. 117 poz., schem.

Twórcy

autor

Rydz J.

Polska Akademia Nauk, Centrum Chemii Polimerów, ul. M. Curie-Skłodowskiej 34, 41-819 Zabrze

autor

Kowalczuk M.

Polska Akademia Nauk, Centrum Chemii Polimerów, ul. M. Curie-Skłodowskiej 34, 41-819 Zabrze

Bibliografia

[1] Y. Doi, Microbial Polyesters, VCH Publishers, New York 1990.
[2] M. Kowalczuk, Plastic Rev., 2001,10, 34.
[3] Z. Jedliński, P. Kurcok, R.W. Lenz, Macromolecules, 1998,31, 6718.
[4] R.A. Gross, A. Kumar, B. Kalra, Chem. Rev., 2001,101,2097.
[5] M. Okada, Prog. Polym. Sci., 2002,27, 87.
[6] A Zaks, A.M. Klibanov, Science, 1984,224, 1249.
[7] E. Haliniarz, B. Lejczak, Wiad. Chem., 1996, 50, 193.
[8] E. Żymańczyk-Duda, B. Lejczak, Wiad. Chem., 1997,51,293.
[9] RD. Schmid, R. Verger, Angew. Chem. Int. Ed., 1998,37, 1608.
[10] H. Nishida, M. Yamashita, M. Nagashima, T. Endo, Y. Tokiwa, J. Polym. Sci., Part A: Polym. Chem., 2000,38, 1560.
[11] S. Kobayashi, H. Uyama, S. Kimura, Chem. Rev., 2001,101, 3793.
[12] L.A. Henderson, Y.Y. Svirkin, R.A. Gross, D.L. Kaplan, G. Swift, Macromolecules, 1996, 29, 7759.
[13] Y. Osanai, K. Toshima, S. Matsumura, Chem. Lett., 2000, 576.
[14] S. Shoda, S. Kobayashi, Macromol. Symp., 1995, 99, 179.
[15] R. Ikeda, J. Sugihara, H. Uyama, S. Kobayashi, Macromolecules, 1996, 29, 8702.
[16] G. Mezoul, T. Lalot, M. Brigodiot, E. Marechal, Polym. Bull., 1996, 36, 541.
[17] S. Kobayashi, J. Polym. Sci., Part A: Polym. Chem., 1999,37, 3041.
[18] S. Matsumura, J. Takahashi, Macromol. Chem., Rapid Commun., 1986,7, 396.
[19] D. O’Hagan, N.A. Zaidi, Polymer, 1994,35, 3576.
[20] X. Shuai, Z. Jedliński, M. Kowalczuk, J. Rydz, H. Tan, Eur. Polym. J., 1999,35, 721.
[21] M. Runge, D. O'Hagan, G. Haufe, J. Polym. Sci., Part A: Polym. Chem. 2000,38, 2004.
[22] D. O’Hagan, A.H. Parker, Polym. Bull., 1998,41, 519.
[23] D. Knani, A.L. Gutman, D.H. Kohn, J. Polym. Sci., Part A: Polym. Chem., 1993,31, 1221.
[24] D. Knani, D.H. Kohn, J. Polym. Sci., Part A: Polym. Chem., 1993,31, 2887.
[25] K. Faber, S. Riva, Synthesis, 1992, 895.
[26] Z. Chalecki, J. Plenkiewicz, Wiad. Chem., 1998,52, 545.
[27] A.W.P. Jarvie, B.K. Samra, A. J. Wiggett, J. Chem. Research (S), 1996, 129.
[28] H. Uyama, S. Kobayashi, Chem. Lett., 1994, 1687.
[29] H. Uyama, S. Yaguchi, S. Kobayashi, J. Polym. Sci., Part A: Polym. Chem., 1999,37,2737.
[30] H. Uyama, S. Yaguchi, S. Kobayashi, Polym. J., 1999,31, 380.
[31] T. Takamoto, H. Uyama, S. Kobayashi, e-Polymers on-line, 2001,4, 1.
[32] J.S. Wallace, C.J. Morrow, J. Polym. Sci., Part A: Polym. Chem., 1989,27, 3271.
[33] G. Mezoul, T. Lalot, M. Brigodiot, E. Marechal, Macromol. Rapid Commua., 1995,16, 613.
[34] G. Mezoul, T. Lalot, M. Brigodiot, E. Marechal, J. Polym. Sci., Part A: Polym. Chem., 1995,33, 2691.
[35] C. Berkane, G. Mezoul, T. Lalot, M. Brigodiot, E. Marechal, Macromolecules, 1997, 30, 7729.
[36] S. Kobayashi, H. Uyama, Macromol. Chem., Rapid Commun., 1993,14, 841.
[37] S. Matsumura, T. Okamoto, K. Tsukada, K. Toshima, Macromol. Rapid Commun., 1998, 19,295.
[38] J.S. Wallace, C.J. Morrow, J. Polym. Sci., Part A: Polym. Chem., 1989,27,2553.
[39] H. Uyama, K. Inada, S. Kobayashi, Macromol. Rapid Commun., 1999,20, 171.
[40] H. Uyama, K. Inada, S. Kobayashi, Macromol. Biosci., 2001,1,40.
[41] B.J. Kline, E.J. Beckman, A.J. Russel, J. Am. Chem. Soc., 1998,120, 9475.
[42] J.S. Wallace, K.B. Reda, M.E. Williams, C.J. Morrow, J. Org. Chem., 1990, 55, 3544.
[43] F. Binns, P. Harffey, S.M. Roberts, A. Taylor, J. Polym. Sci., Part A: Polym. Chem., 1998,36,2069.
[44] Z.-L. Wang, K. Hiltunen, P. Orava, J. Seppala, Y.-Y. Linko, J. Macromol. Sci., Pure Appl. Chem., 1996, A33, 599.
[45] H. Uyama, K. Inada, S. Kobayashi, Polym. J., 2000, 32,440.
[46] S. Kobayashi, H. Uyama, S. Suda, S. Namekawa, Chem. Lett., 1997, 105.
[47] G.A.R. Nobes. R.J. Kazlauskas, R.H. Marchessault, Macromolecules, 1996, 29,4829.
[48] H. Uyama, K. Takeva, S. Kobayashi, Bull. Chem. Soc. Jpn., 1995,68, 56.
[49] H. Uyama, S. Namekawa, S. Kobayashi, Polym. J., 1997, 29,299.
[50] S. Matsumura, H. Ebata, K. Toshima, Macromol. Rapid Commun., 2000,21, 860.
[51] S. Kobayashi, K. Takeya, S. Suda, H. Uyama, Macromol. Chem. Phys., 1998,199, 1729.
[52] A. Cordova, T. Iversen, K. Huit, M. Martinelle, Polymer, 1998, 39, 6519.
[53] A. Kumar, R.A. Gross, Biomacromolecules, 2000,1, 133.
[54] H. Ebata, K. Toshima, S. Matsumura, Biomacromolecules, 2000,1, 511.
[55] S. Namekawa, H. Uyama, S. Kobayashi, Polym., J. 1996,28, 730.
[56] S. Matsumura, H. Beppu, K. Nakamura, S. Osanai, K. Toshima, Chem. Lett., 1996, 795.
[57] S. Matsumura, Y. Suzuki, K. Tsukada, K. Toshima, Y. Dot, K. Kasuya, Macromolecules, 1998, 31, 6444.
[58] H. Dong, S-G. Cao, Z-Q. Li, S-P. Han, D-L. You, J-C. Shen, J. Polym. Sci., Part A: Polym. Chem., 1999,37, 1265.
[59] Y. Suzuki, T. Ohura, K. Kasuya, K. Toshima, S. Matsumura, Chem. Lett., 2000,318.
[60] A. Kumar, R.A. Gross, D. Jendrossek, J. Org. Chem., 2000,65,7800.
[61] W. Xie, J. Li, D. Chen, P.G. Wang, Macromolecules, 1997, 30, 6997.
[62] Y.Y. Svirkin, J. Xu, R.A. Gross, D.L. Kaplan, G. Swift, Macromolecules, 1996,29,4591.
[63] H. Kikuchi, H. Uyama, S. Kobayashi, Macromolecules, 2000,33, 8971.
[64] R.W. Bates, R. Femandez-Moro, S.V. Ley, Tetrahedron Lett., 1991,32, 2651.
[65] Y. Koichi, K. Suginaka, Y. Yamamoto, J. Chem. Soc. Perkin Trans. 1, 1995, 1645.
[66] J. Xu, Gross, R. A.; Kaplan, D. L. Swift, G. Macromolecules, 1996,29,3857.
[67] J. Xu, Gross, R. A.; Kaplan, D. L. Swift, G. Macromolecules, 1996, 29,4582.
[68] H. Uyama, S. Kobayashi, Polymer Preprints Am. Chem. Soc., 1994,35,444.
[69] S. Kobayashi, H. Uyama, S. Namekawa, H. Hayakawa, Macromolecules, 1998, 31, 5655.
[70] H. Uyama, S. Kobayashi, M. Monta, S. Habaue, Y. Okamoto, Macromolecules, 2001,34, 6554.
[71] A. Duda, A. Kowalski, S. Penczek, H. Uyama, S. Kobayashi, Macromolecules, 2002,35,4266.
[72] H. Uyama, H. Kikuchi, K. Takeya, S. Kobayashi, Acta Polym., 1996,47,357.
[73] K.S. Bisht, L.A. Henderson, R.A. Gross, D.L. Kaplan, G. Swift, Macromolecules, 1997,30, 2705.
[74] S. Namekawa, H. Uyama, S. Kobayashi, Polym. J., 1998,30,269.
[75] S. Kobayashi, H. Uyama, S. Namekawa, Polym. Degrad. Stabil., 1998, 59,195.
[76] S. Kobayashi, H. Uyama, T. Takamoto, Biomacromolecules, 2000,1, 3.
[77] H. Uyama, S. Suda, H. Kikuchi, S. Kobayashi, Chem. Lett., 1997,1109.
[78] K. Kullmer, H. Kikuchi, H. Uyama, S. Kobayashi, Macromol. Rapid Commun., 1998,19, 127.
[79] K.S. Bisht, R Deng, R.A. Gross, D.L. Kaplan, G. Swift, J. Am. Chem. Soc., 1998,120, 1363.
[80] A. Cordova, T. Iversen, K. Hult, Macromolecules, 1998,31, 1040.
[81] A. Cordova, Biomacromolecules, 2001, 2, 1347.
[82] F. Deng, K.S. Bisht, R.A. Gross, D.L. Kaplan, Macromolecules, 1999, 32, 5159.
[83] A. Cordova, A. Hult, K. Hult, H. Ihre, T. Iversen, E. Malmstrom, J. Am. Chem. Soc., 1998, 120, 13521.
[84] S. Kobayashi, H. Uyama, [w:] Encyclopedia of Polymer Science and Technology, John Wiley & Sons, on-line, 2002.
[85] Z. Jedliński, M. Kowalczuk, G. Adamus, W. Sikorska, J. Rydz, Int. J. Biol. Macromol., 1999, 25, 247.
[86] X. Skuai, Q. Luo, Z. Jedliński, Chinese Chemistry on-line, 1999,1-12, 99043.
[87] S. Namekawa, H. Uyama, S. Kobayashi, Biomacromolecules, 2000,1,335.
[88] S. Namekawa, H. Uyama, S. Kobayashi, International Symposium on Biological Polyhydroxyalkanoates, Riken, Japan 1998, P-63.
[89] S. Namekawa, H. Uyama, S. Kobayasni, Macromol. Chem. Phys., 2001, 202, 801.
[90] A. Kumar, R.A. Gross, J. Am. Chem. Soc., 2000,122, 11767.
[91] T. Takamoto, P. Kerep, H. Uyama, S. Kobayashi, Macromol. Biosci., 2001,1, 223.
[92] A. Kumar, B. Kalra, A. Dekhterman, R.A. Gross, Macromolecules, 2000,33,6303.
[93] H. Uyama, H. Kikuchi, S. Kobayashi, Chem. Lett., 1995, 1047.
[94] A. Cordova, T. Iversen, K. Hult, Polymer, 1999,40,6709.
[95] H. Uyama, H. Kikuchi, S. Kobayashi, Bull. Chem. Soc. Jpn., 1997, 70, 1691.
[96] Y. Feng, J. Knufermann, D. Klee, H. Hocker, Macromol. Chem. Phys., 1999, 200, 1506.
[97] R.T. MacDonald, S.K. Pulapura, Y.Y. Svirkin, R.A. Gross, D.L. Kaplan, J. Akkara, G. Swift, S. Wolk, Macromolecules, 1995, 28, 73.
[98] A.L. Gutman, T. Bravo, J. Org. Chem., 1989, 54,4263.
[99] A.L. Gutman, K. Zuobi, T. Bravo, J. Org. Chem., 1990, 55,3546.
[100] G. Zhi-Wei, Ch.J. Sih, J. Am. Chem. Soc., 1988,110, 1999.
[101] S. Matsumura, S. Harai, K. Toshima, Macromol. Rapid Commun., 2001,22,215.
[102] K.S. Bisht, Y.Y. Svirkin, L.A. Henderson, R.A. Gross, D.L. Kaplan, G. Swift, Macromolecules, 1997,30, 7735.
[103] T.F. AI-Azemi, K.S. Bisht, Macromolecules, 1999, 32, 6536.
[104] R.A. Gross, B. Kalra, A. Kumar, Appl. Microbiol. Biotechnol., 2001, 55,655.
[105] S. Matsumura, K. Tsukada, K. Toshima, Macromolecules, 1997, 30, 3122.
[106] S. Matsumura, S. Harai, K. Toshima, Macromol. Chem. Phys., 2000, 201, 1632.
[107] S. Namekawa, H. Uyama, S. Kobayashi, H.R. Kricheldorf, Macromol. Chem. Phys., 2000, 201, 261.
[108] S. Matsumura, K. Mabuchi, K. Toshima, Macromol. Rapid Commun., 1997,18,477.
[109] S. Matsumura, K. Mabuchi, K. Toshima, Macromol. Symp., 1998,130, 285.
[110] H. Dong, H.D. Wang, S.G. Cao, J.C. Shen, Biotechnol. Lett., 1998, 20, 905.
[111] S. Matsumura, K. Tsukada, K. Toshima, Int. J. Biol. Macromol., 1999,25, 161.
[112] J. Otera, Chem. Rev., 1993, 93, 1449.
[113] E. Rubio, A. Femandez-Mayorales, A.M. Klibanov, J. Am. Chem. Soc., 1991,113, 695.
[114] S. Tawaki, A.M. Klibanov, J. Am. Chem. Soc., 1992,114, 1882.
[115] H. Uyama, K. Takeya, N. Hoshi, S. Kobayashi, Macromolecules, 1995, 28, 7046.
[116] A.M. Klibanov, Nature, 2001,409, 241.
[117] A. Schmid, J.S. Dordick, B. Hauer, A. Kiener, M. Wubbolts, B. Witholt, Nature, 2001,409, 258.

Typ dokumentu

Bibliografia

Identyfikator YADDA

bwmeta1.element.baztech-article-BUS2-0001-0052