Non-conventional hydrolase chemistry: Amide and carbamate bond formation catalyzed by lipases

Bioorganic and Medicinal Chemistry

Volumn 7, Issue 10, 1999, Pages 2189-2197

  Gotor, Vicente ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

Alkoxycarbonylation; Amides; Amines; Aminolysis; Ammonolysis; Biocatalysis; Biotransformations; Carb amates; Enzymes; Lipases

Indexed keywords

AMIDE; CARBAMIC ACID; HYDROLASE; TRIACYLGLYCEROL LIPASE;

ACYLATION; AMIDATION; CATALYSIS; CHEMICAL BINDING; ENZYME ACTIVITY; ENZYME MECHANISM; REVIEW; SYNTHESIS;

ALCOHOLS; AMIDES; AMINES; CARBAMATES; CATALYSIS; ESTERS; HYDROLASES; LIPASE; QUATERNARY AMMONIUM COMPOUNDS;

EID: 0032825993     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(99)00150-9     Document Type: Review

References (104)

1. Wong, C. H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry, Tetrahedron Organic Chemistry Series; Pergamon, 1994, Vol 12.
2. Drauz, K.; Waldmann, H. Enzyme Catalysis in Organic Synthesis; VCH, 1995.
3. Roberts, S. M.; Turner, N. J.; Willets, A. J.; Turner, M. K. Introduction to Biocatalysis using Enzymes and Micro-Organisms; Cambridge University Press, 1995.
4. Faber K. Biotranformations in Organic Chemistry. 3rd ed. 1997;Springer-Verlag, Berlin. 1997.
5. Theil F. Chem. Rev. 95:1995;2203-2227.
6. Kazlauskas R.J., Bornscheuer U.T Biotransformations with lipases. Rehm H.J., Reed G., Pühler A., Stadler P., Kelly D.R. Biolechnology. 1998;37-91 VCH, Weinheim. pp. 37-91.
7. Klibanov A.M. Acc. Chem. Res. 23:1990;114-120.
8. Santaniello E., Ferraboschi P., Grisenti P., Manzochi A. Chem. Rev. 92:1992;1071-1140.
9. Santaniello E., Ferraboschi P., Grisenti P. Enzyme Microb. Technol. 15:1993;367-382.
10. Roberts, S. M. J. Chem. Soc. Perkin Trans 1 1998, 157-169.
11. Ferrero M., Fernández S., Gotor V. J. Org. Chem. 62:1997;4358-4363.
12. Nakamura K., Kinoshita M., Ohno A. Tetrahedron. 50:1994;4681-4690.
13. Kirchen G., Scollar M.D., Klibanov A.M. J. Am. Chem. Soc. 107:1985;7072-7076.
14. Degueil-Castaing M., de Jeso B., Dronillard S., Maillard B. Tetrahedron Lett. 28:1987;953-954.
15. Blanchi D., Cesti P., Battistel E. J. Org. Chem. 53:1988;5531-5534.
16. Ghogare, A.; Kumar, G. S. J. Chem. Soc., Chem. Commun. 1989, 1533-1535.
17. Frykman H., Öhrner N., Norin T., Hult K. Tetrahedron Lett. 34:1993;1367-1370.
18. Kita Y., Takabe Y., Murata K., Naka T., Akai S. Tetrahedron Lett. 37:1996;7369-7372.
19. Zaks A., Kilbanov A.M. Proc. Natl. Acad. Sci. USA. 82:1985;3192-3196.
20. Margolin A.L., Klibanov A.M. J Am. Chem. Soc. 109:1987;3802-3804.
21. West J.B., Wong C.-H. Tetrahedron Lett. 28:1987;1629-1632.
22. Gotor V., Brieva R., Rebolledo F. Tetrahedron Lett. 29:1988;6973-6974.
23. Gotor V., García M.J., Rebolledo F. Tetrahedron: Asymmetry. 1:1990;277-278.
24. Brieva, R.; Rebolledo, F.; Gotor, V. J Chem. Soc., Chem. Commun. 1990, 1386-1387.
25. Tuccio B., Ferré F., Comeau L. Tetrahedron Lett. 32:1991;2763-2764.
26. Djeghaba Z., Deleuze H., de Jeso B., Messadi D., Maillard B. Tetrahedron Lett. 32:1991;761-762.
27. Bistline R.G. Jr., Bilyk A., Feairheller S.H. J. Am. Oil Chem. Soc. 68:1991;95-98.
28. Kobata K., Yoshikawa Y., Kohashi K., Watanabe T. Tetrahedron Lett. 37:1996;2789-2790.
29. Kobata K., Kawamura, Toyoshima M., Tamura Y., Ogawa S., Watanabe T. Biotechnol. Lett. 20:1998;451-454.
30. Gotor V., Brieva R., González C., Rebolledo F. Tetrahedron. 47:1991;9207-9214.
31. Quirós M., Sanchez V.M., Brieva R., Rebolledo F., Gotor V. Tetrahedron: Asymmetry. 4:1993;1105-1112.
32. Vórde C., Horberg H.-E., Hedenström E. Tetrahedron: Asymmetry. 7:1996;1507-1513.
33. Adamczyk M., Grote J. Tetrahedron Lett. 37:1996;7913-7916.
34. Adamczyk M., Grote J., Rege S. Tetrahedron: Asymmetry. 8:1997;2509-2512.
35. De Zoete M.C., Kock-van Dalen A.C., van Rantwijk F., Sheldon R.A. J. Molec. Catat B: Enzym. 2:1996;19-25.
36. Gotor, V. In Microbial Reagents in Organic Synthesis, NATO ASI Ser. C381, Servi, S., Ed.; Kluwer Acad. Pub.: The Netherlands, 1992, pp 199-208.
37. Rebolledo F., Brieva R., Gotor V. Tetrahedron Lett. 30:1989;5345-5346.
38. Puertas S., Brieva R., Rebolledo F., Gotor V. Tetrahedron. 49:1993;4007-4014.
39. Gotor, V.; Menéndez, E.; Mouloungui, Z.; Gaset, A. J. Chem. Soc. Perkin Trans. 1 1993, 2453-2456.
40. Garcia M.J., Rebolledo F., Gotor V. Tetrahedron: Asymmetry. 3:1992;1519-1522.
41. García M.J., Rebolledo F., Gotor V. Tetrahedron: Asymmetry. 4:1993;2199-2210.
42. Gutman A.L., Meyer E., Yue X., Abell C. Tetrahedron Lett. 33:1992;3943-3946.
43. Garcia M.J., Rebolledo F., Gotor V. Tetrahedron Lett. 34:1993;6141-6142.
44. De Zoete, M. C.; Kock-van Dalen, A. C.; van Rantwijk, F.; Sheldon, R. A. J. Chem. Soc., Chem. Commun. 1993, 1831-1832.
45. Chen, S.-T.; Jang, M.-K.; Wang, K.-T. Synthesis, 1993, 858-860.
46. De Zoete, M. C.; Kock-van Dalen, A. C.; van Rantwijk, F.; Sheldon, R. A. J. Molec. Catal. B: Enzym. 1996, 2, 141-145.
47. Sanchez, V.; Rebolledo, F.; Gotor, V. Synlett. 1994, 529-530.
48. Quirós M., Astorga C., Rebolledo F., Gotor V. Tetrahedron. 51:1995;7715-7720.
49. Garcia M.J., Rebolledo F., Gotor V. Tetrahedron. 50:1994;6935-6940.
50. De Zoete M.C., Ouwehand A.A., van Rantwijk F., Sheldon R.A. Rec. Trav. Chim. Pays-Bas. 114:1995;171-174.
51. Hacking M.A.P.J., Wegman M.A., Rops J., van Rantwiik A., Sheldon R.A. J. Molec. Catal. B: Enzym. 5:1998;155-157.
52. Kanerva L.T., Csomós P., Sundholm O., Bernáth G., Fülöp F. Tetrahedron: Asymmetry. 7:1996;1705-1716.
53. Sánchez V., Rebolledo F., Gotor V. Tetrahedron: Asymmetry. 8:1997;37-40.
54. Starmans W.A.J., Doppen R.G., Thijs L., Zwanenburg B. Tetrahedron: Asymmetry. 9:1998;429-435.
55. Puertas S., Rebolledo F., Gotor V. J. Org. Chem. 61:1996;6024-6027.
56. Kagan, H. B. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic: Orlando, 1985 pp 1-39.
57. Coppola, G. M.; Schuster, H. F. In Asymmetric Synthesis; Wiley: New York, 1987.
58. Kitaguchi H., Fitzpatrick P.A., Huber J.E., Klibanov A.M. J. Am. Chem. Soc. 111:1989;3094-3095.
59. Gutman A.L., Meyer E., Kalerin E., Polyak F., Sterling J. Biolechnol. Bioeng. 40:1992;760-767.
60. Reetz M.T., Dreisbach C. Chimia. 48:1994;570.
61. Reetz M.T., Schimossek K. Chimia. 50:1996;668-669.
62. Jaeger K.-E., Liebeton K., Zonta A., Schimossek K., Reetz M.T. Appl. Microbiol. Biotechnol. 46:1996;99-105.
63. Jaeger K.-E., Schneidinger B., Rosenau F., Werner M., Lang D., Dijkstra B.W., Schimossek K., Zonta A., Reetz M.T. J. Molec. Catal. B: Enzym. 3:1997;3-12.
64. Balkenhohl F., Ditrich K., Hauer B., Ladner W. J. Prakt. Chem. 339:1997;381-384.
65. Takaoka Y., Kajimoto T., Wong C.-H. J. Org. Chem. 58:1993;4809-4812.
66. Iglesias L.E., Sánchez V.M., Rebolledo F., Gotor V. Tetrahedron: Asymmetry. 8:1997;2675-2677.
67. Öhrner N., Orrenius Ch., Mattson A., Norin T., Hult K. Enzyme Microb. Technol. 19:1996;328-331.
68. Nishibayashi Y., Arikawa Y., Ohe K., Uemura S. J. Org. Chem. 61:1996;1172-1174.
69. Mattson A., Orrenius Ch., Öhrner N., Unelius C.R., Hult K., Norin T. Acta Chem. Scand. 50:1996;918-921.
70. Alfonso, I.; Astorga, C.; Rebolledo, F.; Gotor, V. J. Chem. Soc., Chem. Commun. 1996, 2471-2472.
71. Kazlauskas R.J., Weissfloch A.N.E. J. Molec. Catal. B: Enzym. 3:1997;65-72.
72. De Castro M.S., Sinisterra Gago J.V. Tetrahedron. 54:1998;2877-2892.
73. Chinsky N., Margolin A.L., Klibanov A.M. J. Am. Chem. Soc. 111:1989;386-388.
74. Furutani T., Furui M., Oshima H., Kato J. Enzyme Microb. Technol. 19:1996;578-584.
75. Gotor, V.; Brieva, R.; Rebolledo, F. J. Chem. Soc., Chem. Commun. 1988, 957-958.
76. Fernández, S.; Brieva, R.; Rebolledo, F.; Gotor, V. J. Chem. Soc. Perkin Trans. 1 1992, 2885-2889.
77. Bevinakatti H.S., Newadkar R.V. Tetrahedron: Asymmetry. 1:1990;583-586.
78. Francalanci R., Cesti P., Cabri W., Bianchi D., Martinengo T., Foà M. J. Org. Chem. 52:1987;5079-5082.
79. Lundell K., Kanerva L.T. Tetrahedron: Asymmetry. 6:1995;2281-2286.
80. Maestro A., Astorga C., Gotor V. Tetrahedron: Asymmetry. 8:1997;3153-3159.
81. Asensio G., Andreu C., Marca J.A. Tetrahedron Lett. 32:1991;4197-4198.
82. Djeghaba Z., De Jeso B. Bull. Soc. Chim. Belg. 104:1995;161-164.
83. Chiou T.-W, Chang C-C., Lai C.-T., Tai D.-F. Bioorg. Med. Chem. Lett. 7:1997;433-436.
84. Maugard T., Remaud-Simeon M., Petre D., Monsan P. Tetrahedron. 53:1997;7587-7594.
85. Maugard T., Remaud-Simeon M., Petre D., Monsan P. J. Molec. Catal. B: Enzym. 5:1998;13-17.
86. Puertas S., Rebolledo F., Gotor V. Tetrahedron. 51:1995;1495-1502.
87. Chamorro C., González-Muñiz R., Conde S. Tetrahedron: Asymmetry. 6:1995;2343-2352.
88. Conde S., López-Serrano P., Fierros M., Biezma M.I., Martinez A., Rodríguez-Franco M.I. Tetrahedron. 53:1997;11745-11752.
89. Conde S., López-Serrano P., Martinez A. Biotechnol. Lett. 20:1998;261-263.
90. Astorga C., Rebolledo F., Gotor V. J. Chem. Soc. Perkin Trans. 1:1994;829-832.
91. Quirós, M.; Rebolledo, F.; Gotor, V. J. Chem. Research. (S) 1994, 339.
92. Pioch D., Lozano P., Graille J. Biotechnol. Lett. 13:1991;633-636.
93. Pulido R., Gotor V. Carbohyd. Res. 252:1994;55-68.
94. Morís F., Gotor V. J. Org. Chem. 57:1992;2490-2492.
95. Morís F., Gotor V. Tetrahedron. 48:1992;9869-9876.
96. García-Alles L.F., Morís F., Gotor V. Tetrahedron Lett. 34:1993;6337-6338.
97. Matassa V.G., Maduskuie T.P., Shapiro H.S., Hesp B., Snyder D.W., Aharony D., Krell R.D., Keith R.A. J. Med. Chem. 33:1990;1781-1790.
98. Ghosh A.K., Duong T.T., McKee S.P., Thompson W.J. Tetrahedron Lett. 33:1992;2781-2784.
99. Pozo M., Pulido R., Gotor V. Tetrahedron. 48:1992;6477-6484.
100. Pozo M., Gotor V. Tetrahedron. 49:1993;4321-4326.
101. Pozo M., Gotor V. Tetrahedron. 49:1993;10725-10732.
102. Pozo M., Gotor V. Tetrahedron: Asymmetry. 6:1995;2797-2802.
103. Orsat B., Alper P.B., Moree W.J., Mak C.-P., Wong C.-H. J. Am. Chem. Soc. 118:1996;712-713.
104. Takayama S., Moree W.J., Wong C.-H. Tetrahedron Lett. 37:1996;6287-6290.