Zastosowanie lipaz w syntezie organicznej w środowisku bezwodnym

Chalecki, Z.; Plenkiewicz, J.

Artykuł - szczegóły

Tytuł artykułu

Zastosowanie lipaz w syntezie organicznej w środowisku bezwodnym

Autorzy

Chalecki Z. , Plenkiewicz J.

Wybrane pełne teksty z tego czasopisma

Identyfikatory

Warianty tytułu

The use of lipases in organic synthesis in nonaqueous media

Języki publikacji

Abstrakty

In nature the enzymatic reactions are conduced in aqueous media. However for the purpose of organic synthesis nonaqueous conditions such as organic solvents are more suitable regarding reagents stability and reaction equilibrium. Rapidly increasing number of enzyme-catalysed processes shows great possibility of this domain of chemistry. This review presents methods that have been used in lipase-catalysed esterifications and transenterifiacations in nonaqueous media. We show many examples of resolution of racemic alcohols and acids using different lipases in different reaction conditions. We also present a few examples of highly regioselective properties of lipases. There are descibed general principles that govern lipase-catalysed reactions and historical development of biocatalysis in organic synthesis. We hope that this review will be helpful for the investigators and students in solving their problems of enzymatic synthesis.

Słowa kluczowe

enzym reakcja enzymatyczna synteza enzymatyczna alkohole lipazy kwasy karboksylowe

enzyme lipases acids organic synthesis

Wydawca

Polskie Towarzystwo Chemiczne

Czasopismo

Wiadomości Chemiczne

Rocznik

1998

Tom

[Z] 52, 7-8

Strony

545--568

Opis fizyczny

schem., bibliogr. 142 poz.

Twórcy

autor

Chalecki Z.

Zakład Technologii i Biotechnologii Środków Leczniczych, Wydział Chemiczny, Politechnika Warszawska, ul. Koszykowa 75, 00-662 Warszawa

autor

Plenkiewicz J.

Zakład Technologii i Biotechnologii Środków Leczniczych, Wydział Chemiczny, Politechnika Warszawska, ul. Koszykowa 75, 00-662 Warszawa

Zakład Technologii i Biotechnologii Środków Leczniczych, Wydział Chemiczny, Politechnika Warszawska, ul. Koszykowa 75, 00-662 Warszawa

Bibliografia

[1] J. Kączkowski, Podstawy biochemii, WNT, wyd. XI, Warszawa 1996.
[2] S. Kotha, Tetrahedron, 1994, 50, 3639.
[3] D. Koshland, K. Neet, Ann. Rev. Biochem., 1968, 37, 359.
[4] F. Bjorkling, J. Boutelje, S. Gatenbeck, K. Hult, T. Norin, P. Szmulik, Tetrahedron, 1985, 41, 1347.
[5] L. K. P. Lam, R. A. H. F. Hui, J. B. Jones, J. Org. Chem., 1986, 51, 2047.
[6] J. Boutelje, M. Hjalmarsson, P. Szmulik, T. Norin, K. Hult. [w:] Biocatalysis in Organic Media, C. Laane, J. Tramper, M. D. Lilly (red.), Elsevier, Amsterdam 1987.
[7] J. Zemlicka, L. E. Craine, M.-J. Heeg, J. P. Oliver, J. Org. Chem., 1988. 53. 93.
[8] E. J. Toone, M. J. Werth, J. B. Jones, J. Am. Chem. Soc., 1990, 112, 4946.
[9] J. Uppenberg, M. T. Hansen, S. Patkar, T. A. Jones, Structure, 1994, 2, 293.
[10] R. J. Kazlauskas, Tibtech, 1994, 12, 464.
[11] D. Rotticci, C. Orrenius, K. Huit, T. Norin, Tetrahedron: Asymmetry. 1997, 8, 359.
[12] J. Crosby, Tetrahedron, 1991, 47, 4789.
[13] P. Kafarski, B. Lejczak, Chemia bioorganiczna, PWN, Warszawa 1994.
[14] W. Hartmeier, Immobilized Biocatalysts, Springer-Verlag, Berlin, Heidelberg 1988.
[15] P. C. de Jesus, M. C. Rezende, M. da Graęa Nascimento., Tetrahedron: Asvmmetry, 1995, 6, 63.
[16] G. Langrand, M. Secchi, G. Buono, J. Baratti, C. Triantaphylides, Tetrahedron Lett., 1985, 26, 1857.
[17] E. L. A. Macfarlane, S. M. Roberts, N. J. Turner, J. Chem. Soc., Chem. Commun., 1990. 569.
[18] P. W. Fowler, E. L. A. Macfarlane, S. M. Robert, ibid., 1991, 453.
[19] A. J. M. Janssen, A. J. H. Klunder, B. Zwanenburg, Tetrahedron, 1991, 47, 7645.
[20] B. Cambou, A. M. Klibanov, J. Am. Chem. Soc., 1984, 106, 2687.
[21] G. Kirchner, M. P. Scollar, A M. Klibanov, ibid., 1985, 107, 7072.
[22] P. D. Theisen, C. H. Heathcock, J. Org. Chem., 1988, 53, 2374.
[23] T. M. Stokes, A. C Oehlschlager, Tetrahedron Lett.,, 1987, 28, 2091.
[24] B. Morgan, A. C. Oehlschlager, T. M. Stokes, Tetrahedron, 1991, 47, 1611.
[25] B. Morgan, A. C. Oehlschlager, T. M. Stokes, J. Org. Chem. 1992, 57, 3231.
[26] J. Hiratake, M. Inagaki, T. Nishioka, J. Oda, ibid., 1988, 53, 6130.
[27] P. E. Sonnet, ibid., 1987, 52, 3477.
[28] T. Keumi, Y. Hiraoka, T. Ban, I. Takahashi, H. Kitajima, Chem. Let., 1991, 1989.
[29] H. M. Sweers, C.-H. Wong, J. Am. Chem. Soc., 1986, 108, 6421.
[30] M. Degueil-Castaing, B. de Jeso, S. Drouillard, B. Maillard, Tetrahedron Lett., 1987, 28, 953.
[31] Y.-F. Wang, C.-H. Wong, J. Org. Chem., 1988, 53, 3127.
[32] Y.-F. Wang, J. J. Lalonde, M. Momogan, D. E. Bergbreiter, C.-H. Wong, J. Am. Chem. Soc., 1988, 110, 7200.
[33] K. Laumen, D. Breitgoff, M. P. Schneider, J. Chem. Soc., Chem. Commun.. 1988, 1459.
[34] Y.-F. Wang, S.-T. Chen, K. K.-C. Liu, C.-H. Wong, Tetrahedron Lett.. 1989, 30, 1917.
[35] G. E. Jeromin, A. Scheidt, ibid., 1991, 32, 7021.
[36] P. A. Fitzpatrick, A M. Klibanov, J. Am. Chem. Soc., 1991, 113, 3166.
[37] U. Goergens, M. P. Schneider, J. Chem. Soc., Chem. Commun., 1991, 1065.
[38] H. E. Master, R V. Newadkar, R A Rane, A. Kumar, Tetrahedron Lett., 1996, 37, 9253.
[39] J. Faraldos, E. Arroyo, B. Herradon, Synlett, 1997, 367.
[40] Z. Chalecki, E. Guibe-Jampel, J. Plenkiewicz, Synth. Commun., 1997, 27, 1217.
[41] B. Berger, K. Faber, J. Chem. Soc., Chem. Commun., 1991, 1198.
[42] G. E. Jeronim, V. Welsch, Tetrahedron Lett., 1995, 36, 6663.
[43] K. Suginaka, Y. Hayashi, Y. Yamamoto, Tetrahedron: Asymmetry, 1996, 7, 1153.
[44] A. Payne, C. G. Rabiller, K. Faber, rezultaty nie opublikowane.
[45] H. S. Bevinakatti, R. V. Newadkar, Tetrahedron: Asymmetry, 1993, 4, 773.
[46] D. Bianchi, P. Cesti, E. Batistel, J. Org. Chem., 1988, 53, 5531.
[47] A. L. Gutman, D. Brenner, A. Boltanski, Tetrahedron: Asymmetry, 1993, 4, 839.
[48] G. Ottolina, G. Carrera, S. Riva, Biocatalysis, 1991, 5, 131.
[49] B. Berger, C. G. Rabiller, K. Konigsberger, K. Faber, H. Griengl, Tetrahedron: Asymmetry, 1990, 1, 541.
[50] A. Ghogare, G. S. Kumar, J. Chem. Soc., Chem. Commun, 1989, 1533.
[51] M. Mischitz, U. Poschl, K. Faber, Biotechnol. Lett., 1991, 13, 653.
[52] Q.-M. Gu, C.-S. Chen, C. J. Sih, Tetrahedron Lett., 1986, 27, 1763.
[53] M. Ahmar, C. Girard, R. Bloch, ibid., 1989, 30, 7053.
[54] J. J. Lalonde, C. Govardhan, N. Khalaf, A. G. Martinez, K. Visuri, A. L. Margolin, J. Am. Chem. Soc., 1995, 117, 6845.
[55] J. M. Moreno, J. V. Sinisterra, J. Mol. Cat. A: Chemical, 1995, 98, 171.
[56] I. J. Colton, S. N. Ahmed, R. J. Kazlauskas, J. Org. Chem., 1995, 60, 212.
[57] H. Kitaguchi, I. Itoh, M. Ono, Chem. Lett,, 1990, 1203.
[58] S.-H. Pan, T. Kawamoto, T. Fukui, K. Sonomoto, A. Tanaka, Appl. Microbiol. Bio-technol., 1990, 34, 47.
[59] T. Fukui, T. Kawamoto, K Sonomoto, A. Tanaka, Appl. Microbiol. Biotechnol-, 1990, 34, 330.
[60] P. W. Fowler, E. L. A. Macfarlane, S. M. Roberts, J. Chem. Soc., Chem. Commun., 1991, 453.
[61] S. Parida, J. S. Dordick, J. Am. Chem. Soc., 1991, 113, 2253.
[62] S.-H. Wu, F.-Y. Chu, K.-T. Wang, Bioorg. Med. Chem. Lett., 1991, 1, 339.
[63] E. Holmberg, M. Holmąuist, E. Hedenstrom, P. Berglund, T. Norin, H.-E. Hogberg, K. Hult, Appl. Microbiol. Biotechnol., 1991, 35, 572.
[64] K. H. Engel, Tetrahedron: Asymmetry, 1991, 2, 165.
[65] K. H. Engel, J. Am. Oil Chem. Soc., 1992, 69, 146.
[66] E Holmberg, K. Hult, Biocatalysis, 1992, 5, 289.
[67] S. Parida, J. S. Dordick, J. Org. Chem., 1993, 58, 3238.
[68] C.-S. Chen, S.-H. Wu, G. Girdaukas, C. J. Sih, J. Am. Chem. Soc., 1987, 109, 2812.
[69] B. Cambou, A. M. Klibanov, Biotechnol. Bioeng, 1984, 26, 1449.
[70] M. C. R. Franssen, H. Jongejan, H. Kooijman, A. L. Spek, N. L. F. L. Camacho Mondril, P. M. A. C. Boavida dos Santos, A. de Groot, Tetrahedron: Asymmetry, 1996, 7, 49..
[71] E. Guibe-Jampel, M. Bassir, Tetrahedron Lett., 1994, 35, 421.
[72] E. Guibe-Jampel, Z. Chalecki, M. Bassir, M. Gelo-Pujic, Tetrahedron, 1996, 52, 4397.
[73] Y. Yamamoto, K. Yamamoto, T. Nishioka, J. Oda, Agric. Biol. Chem., 1988, 52, 3087.
[74] K. Yamamoto, T. Nishioka, J. Oda, Y. Yamamoto, Tetrahedron Lett., 1988, 29, 1717.
[75] J. Hiratake, K. Yamamoto, Y. Yamamoto, J. Oda, ibid., 1989, 30, 1555.
[76] Y. Yamamoto, M. Iwasa, S. Sawada, J. Oda, Agric. Biol. Chem., 1990, 54, 3269.
[77] S. Takano, K. Tanigawa, K. Ogasawara, J. Chem. Soc., Chem. Commun., 1976, 189.
[78] T. Tanaka, S. Kurozumi, T. Toru, S. Miura, M. Kobayashi, S. Ishimoto, Tetrahedron, 1976, 32, 1713.
[79] S. Miura, S. Kurozumi, T. Toru, T. Tanaka, M. Kobayashi, S. Matsubara, S. Ishimoto, ibid, 1976, 32, 1893.
[80] P. Mohr, N. Waespe-Sarcevic, C. Tamm, K. Gawrońska, J. Gawroński, Helv. Chim. Acta, 1983, 66, 2501.
[81] W. E. Ladner, G. M. Whitesides, J. Am. Chem. Soc., 1984, 106, 7250.
[82] M. Schneider, N. Engel, P. Honicke, G. Heinemann, H. Gorisch, Angew. Chem., Int. Ed. Engl., 1984, 23, 67.
[83] Y.-F. Wang, C.-S. Chen, G. Girdaukas, C. J. Sih, J. Am. Chem. Soc., 1984, 106, 3695.
[84] G. Sabbioni, M. L. Shea, J. B. Jones, J. Chem. Soc., Chem. Commun, 1984, 236.
[85] K Laumen, M. Schneider, Tetrahedron Lett, 1984, 25, 5875.
[86] K. Laumen, M. Schneider, ibid., 1985, 26, 2973.
[87] F. Bjorkling, J. Boutelje, S. Gatenbeck, T. Hult, T. Norin, Appl. Microb. Biotechnol., 1985, 21, 16.
[88] W. Kasel, P. G. Hultin, J. B. Jones, J. Chem. Soc., Chem. Commun., 1986, 1563.
[89] H. Hem merle, H.-J. Gais, Tetrahedron Lett., 1987, 28, 3471.
[90] P. G. Hultin, F.-J. Mueseler, J. B. Jones, J. Org. Chem., 1991, 56, 5375.
[91] M. Pottie, J. Van der Eycken, M. Vandewalle, Tetrahedron: Asymmetry 1991,2,329.
[92] H. J. Bestmann, U. C. Philipp, Angew. Chem., Int. Ed. Engl., 1991, 30, 86.
[93] H.-J. Gais, H. Hemmerle, S. Kossek, Synthesis, 1992, 169.
[94] P. Ferraboschi, P. Grisenti, A. Manzocchi, E. Santaniello, Tetrahedron: Asymmetry, 1994, 5, 691.
[95] G. Nicolosi, A Patti, M. Piattelli, C. Sanfilippo, Tetrahedron Lett., 1995, 36, 6545.
[96] S. Riva, A. M. Klibanov, J. Am. Chem. Soc., 1988, 110, 3291.
[97] M. Therisod, A. M. Klibanov, ibid., 1986, 108, 5638.
[98] S. Riva, J. Chopineau, A P. G. Kieboom, A. M. Klibanow, ibid., 1988, 110, 584.
[99] S. L. Regen, A. Singh, G. Oehme, M. Singh, ibid., 1982, 104, 791.
[100] G. M. Ramos Tombo, H.-P. Schar, F. Busquets, O. Ghisalba, Tetrahedron Lett., 1986, 27, 5707.
[101] Y. Terao, M. Murata, K. Achiwa, ibid., 1988, 29, 5173.
[102] K. Tsuji, Y. Terao, K. Achiwa, ibid„ 1989, 36, 6189.
[103] K. Mori, N. Chiba, Liebigs Ann. Chem., 1989, 957.
[104] S. Atsuumi, M. Nakano, Y. Koike, S. Tanaka, M. Ohkubo, Tetrahedron Lett., 1990, 31, 1601.
[105] E. Santaniello, P. Ferraboschi, P. Grisenti, ibid., 1990, 31, 5657.
[106] N. Baba, K. Yoneda, S. Tahara, J. Iwase, T. Kaneko, M. Matsuo, J. Chem. Soc., Chem. Commun., 1990,1281.
[107] P. Cresenti, P. Ferraboschi, A. Manzocchi, E. Santaniello, Tetrahedron, 1992, 48, 3827.
[108] G. Guanti, R. Riva, Tetrahedron: Asymmetry, 1995, 6, 2921.
[109] G. Ottolina, G. Carrea, S. Riva, J. Org. Chem., 1990, 55, 2366.
[110] N. Ohrner, M. Martinelle, A. Mattson, T. Norin, K. Hult, Biotechnol. Lett., 1992, 14, 263.
[111] H. Frykman, N. Ohrner, T. Norin, K. Hult, Tetrahedron Lett., 1993, 34, 1367.
[112] D. Gerlach, P. Schreier, Biocatalysis, 1989, 2, 257.
[113] S. V. Kamat, E J. Beckman, A. J. Russell, J. Am. Chem. Soc., 1993, 115, 8845.
[114] M. A. Jackson, J. W. King, J. Am. Oil Chem. Soc., 1997, 74, 193.
[115] R. A. Persichetti, J. J. Lalonde, C. P. Govardhan, N. K. Khalaf, A. L Margolin, Tetrahedron Lett., 1996, 37, 6507.
[116] Y. Okahata, Y. Fujimoto, K. Ijiro, ibid., 1988, 29, 5133.
[117] H.-E. Hogberg, H. Edlund, P. Berglund, E. Hedenstrom, Tetrahedron: Asymmetry, 1993, 4, 2123.
[118] K. Xu, A. M. Klibanov, J. Am. Chem. Soc., 1996, 118, 9815.
[119] C. Orrenius, T. Norin, K. Hult, G. Carrea, Tetrahedron: Asymmetry, 1995, 66, 3023. [120] K. Nakamura, M. Kinoshita, A. Ohno, Tetrahedron, 1995, 51, 8799.
[121] E. Rubio, A. Fernandez-Mayorales, A. M. Klibanov, J. Am. Chem. Soc., 1991,113, 695.
[122] S. Tawaki, A M. Klibanov, ibid., 1992, 114, 1882.
[123] C. R. Wescott, H. Noritomi, A. M. Klibanov, ibid., 1996, 118, 1-365.
[124] E. Guibe-Jampel, G. Rousseau, Tetrahedron Lett., 1987, 28, 3563.
[125] R. S. Phillips, Tibtech, 1996, 14, 13.
[126] A. M. Klibanov, Acc. Chem. Res., 1990, 23, 114.
[127] M. Arroyo, J. V. Sinisterra, J. Org. Chem., 1994, 59, 4410.
[128] Z. Chalecki, E. Guibe-Jampel, Synth. Commun., 1997, 27, 3847.
[129] J.-R. Carrillo-Munoz, D. Bouvet, E. Guibe-Jampel, A. Loupy, A. Petit, J. Org. Chem., 1996, 61, 7746.
[130] M. Gelo-Pujic, E. Guibe-Jampel, A. Loupy, S. A. Galema, D. Mathe, J. Chem. Soc., Perkin Trans. 1, 1996, 2777.
[131] H. T. Huang, C. Niemann, J. Am. Chem. Soc., 1951, 73, 475.
[132] A. Chmiel, Biotechnologia: podstawy mikrobiologiczne i biochemiczne, PWN, Warszawa 1991.
[133] G. M. Whitesides, C.-H. Wong, Angew. Chem., Int. Ed. Engl., 1985, 24, 617.
[134] J. B. Jones, Tetrahedron, 1986, 42, 3351.
[135] H. Yamada, S. Shimizu, Angew. Chem., Int. Ed. Engl., 1988, 27, 622.
[136] C.-H. Wong, Science, 1989, 244, 1145.
[137] R. Csuk, B. I. Glanzer, Chem. Rev., 1991, 91, 49.
[138] E. Santaniello, P. Ferraboschi, P. Grisenti, A Manzocchi, Chem. Rev., 1992, 92, 1071.
[139] K. Faber, S. Riva, Synthesis, 1992, 895.
[140] J. O ter a, Chem. Rev., 1993, 93, 1449.
[141] C.-H. Wong, G. M. Whitesides, Enzymes in Synthetic Organic Chemistry, Elsevier, Oxford 1994.
[142] R. Azerad, Bull. Soc. Chim. Fr., 1995, 132, 17.

Uwagi

Opracowane ze środków MEiN, umowa nr SONP/SP/546092/2022 w ramach programu "Społeczna odpowiedzialność nauki" - moduł: Popularyzacja nauki i promocja sportu (2022-2023).

Typ dokumentu

Bibliografia

Identyfikator YADDA

bwmeta1.element.baztech-article-BUS1-0002-0076