Enzymatic amidation and alkoxycarbonylation of amines using native and immobilised lipases with different origins: A comparative study

Tetrahedron

Volumn 56, Issue 10, 2001, Pages 1387-1391

  Soledad de Castro, M ^a   Domı�?nguez, Pablo ^a   Sinisterra, José V ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

Amides; Carbamate; Enantioselectivity; Lipase; Resolution of amines

Indexed keywords

ALPHA METHYLBENZYLAMINE; AMINE; CARBAMIC ACID DERIVATIVE; CARBONIC ACID DERIVATIVE; TRIACYLGLYCEROL LIPASE; VINYL DERIVATIVE;

AMIDATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CONTROLLED STUDY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0141576954     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00014-4     Document Type: Article

References (28)

1. (a) Kirchner, G.; Scollar M. P.; Klibanov A. M. J. Am. Chem. Soc. 1985, 107, 7072. (b) Bevinakatti H. S.; Benarji A. A.; Newadkar R. V. J. Org. Chem. 1989, 54, 2453.
2. (a) Kirchner, G.; Scollar M. P.; Klibanov A. M. J. Am. Chem. Soc. 1985, 107, 7072. (b) Bevinakatti H. S.; Benarji A. A.; Newadkar R. V. J. Org. Chem. 1989, 54, 2453.
3. Hendry G.A., Houghton J.D., Brown S.B. New Phytol. 107:1987;255.
4. Adamczyk M., Grote J. Tetrahedron: Asymmetry. 8:1997;2099-2100.
5. (a) García, M. J.; Rebolledom, R.; Gotor, V. Tetrahedron Lett. 1993, 34, 6141-6142. (b) Puertas, S.; Rebolledo, R.; Gotor, V. J. Org. Chem. 1996, 61, 6024-6027.
6. (a) García, M. J.; Rebolledom, R.; Gotor, V. Tetrahedron Lett. 1993, 34, 6141-6142. (b) Puertas, S.; Rebolledo, R.; Gotor, V. J. Org. Chem. 1996, 61, 6024-6027.
7. Zoete M.C., Kock-van Dalen A.C., van Rantwijk F., Sheldon R.A. J. Mol. Catal. B: Enzyme. 2:1996;19-25.
8. Ghosh A.K., McKee S.P., Thompson W.J., Darke P.L., Zugay J.C. J. Org. Chem. 58:1993;1025-1029.
9. Denarié M., Grenouillat D., Malfroot T., Senet J., Sennyey G., Wolf P. Tetrahedron Lett. 33:1987;2781.
10. Pozo M., Gotor V. Tetrahedron. 49:1993;4321-4326.
11. Orsat B., Alper Ph.B., Moree W., Mak Ch.-P., Wong Ch.-H. J. Chem. Soc. 118:1996;712-713.
12. Arroyo M., Sinisterra J.V. J. Org. Chem. 59:1994;4410-4417.
13. (a) Colton, I. J.; Ahmed Sh, N.; Kazlauskas, R. J. J. Org. Chem. 1995, 60, 212-217. (b) Hernáiz, M. J.; Sánchez-Montero, J. M.; Sinisterra, J. V. Tetrahedron 1994, 50, 10749-10760.
14. (a) Colton, I. J.; Ahmed Sh, N.; Kazlauskas, R. J. J. Org. Chem. 1995, 60, 212-217. (b) Hernáiz, M. J.; Sánchez-Montero, J. M.; Sinisterra, J. V. Tetrahedron 1994, 50, 10749-10760.
15. Pleiss J., Fischer M., Schmid R.D. Chem. Phys. Lipids. 93:1998;67-80.
16. Faber K. Biotransformations in Organic Chemistry: A Text Book. 3rd ed. 1997;Springer, Berlin.
17. de Castro M.S., Sinisterra J.V. Tetrahedron. 54:1998;2877-2892.
18. Mustranta A., Forssell P., Poutanen K. Enzyme Microb.Technol. 15:1993;133-139.
19. Domínguez de María P., Sinisterra J.V. Tetrahedron. 55:1999;8555-8566.
20. Carballeira, D.; Sinisterra, J. V. Unpublished data.
21. Iglesias L.E., Sánchez V.M., Rebolledo F., Gotor V. Tetrahedron: Asymmetry. 8:1997;2675-2677.
22. Anderson E.M., Larsson K.M., Kirk O. Biocatal. Biotransformations. 16:1998;181-209.
23. Kitaguchi H., Fitzpatrick P.A., Huber J.E., Klibanov A.M. J. Am. Chem. Soc. 111:1989;3094-3095.
24. Maestro A., Astorga C., Gotor V. Tetrahedron: Asymmetry. 8:1997;3153-3159.
25. Hoegh I., Patkar S., Halkier T., Hansen M.T. Can. J. Bot. 73:(suppl. 1):1995;S869-S875.
26. Rogalska E., Cudrey C., Ferrato F., Verger R. Chirality. 5:1993;24-30.
27. López-Belmonte M.T., Alcántara A.R., Sinisterra J.V. J. Org. Chem. 62:1997;1831-1840.
28. Smidt H., Fischer A., Schmid R.D. Biotechnol. Tech. 10:1996;335-338.