Synthesis of peptides employing Fmoc-/Boc-/Z-amino acid fluorides and activated commercial zinc dust

Letters in Peptide Science - Tập 7 - Trang 41-46 - 2000
Vommina V. Suresh Babu1, Kuppanna Ananda1
1Department of Studies in Chemistry, Central College, Bangalore University, Bangalore, India

Tóm tắt

The coupling of urethane protected amino acidfluorides is accomplished in the presence ofactivated, commercial zinc dust to synthesize severaldi- and tripeptides.The coupling was fast and racemization free. The yieldas well as purity of the peptides was satisfactory.The method was extended for the incorporation ofsterically hindered α,α-dialkylaminoacids and N-methylamino acids as well.

Tài liệu tham khảo

Balram, P., Curr. Opin. Struct. Biol., 2 (1992) 845.

Toniolo, C. and Benedetti, E., ISI Atlas of Science: Biochemistry, Institute of Scientific Information, Philadelphia, PA, 1988, p. 225.

Heimgartuer, H., Angew. Chem. Int. Ed. Engl., 30 (1991) 238.

Humphrey, J.M. and Chamberlin, A.R., Chem. Rev., 97 (1997) 2243.

Ranu, B.C., Majee, A. and Das, A.R., Tetrahedron Lett., 37 (1996) 1109.

Ranu, B.C., Majee, A. and Das, A.R., Tetrahedron Lett., 36 (1995) 4885.

Meshram, H.M., Reddy, G.S., Reddy, M.M. and Yadav, J.S., Tetrahedron Lett., 39 (1998) 4107.

Meshram, H.M., Reddy, G.S., Reddy, M.M. and Yadav, J.S., Tetrahedron Lett., 39 (1998) 4103.

Yadav, J.S., Reddy, G.S., Reddy, M.M. and Meshram, H.M., Tetrahedron Lett., 39 (1998) 3259.

Meshram, H.M., Reddy, G.S., Reddy, M.M. and Yadav, J.S., Tetrahedron Lett., 39 (1998) 4107.

Carpino, L.A., Mansour, E.M.E. and Sadat-Aalaee, D., J. Org. Chem., 56 (1991) 2611.

Carpino, L.A., Sadat-Aalaee, D., Chao, H.G. and De Selms, R.H., J. Org. Chem., 112 (1990) 9651.

Savrda, J., Chertanova, L. and Wakselman, M., Tetrahedron, 50 (1994) 5309.

Carpino, L.A., Mansour, E.M.E. and El-Faham, A., J. Org. Chem., 58 (1993) 4162.

Wenschuh, H., Beyermann, M., Krause, E., Brudel, M., Winter, R., Schumann, M., C arpino, L.A. and Bienert, M., J. Org. Chem., 59 (1994) 3275.

Wenschuh, H., Beyermann, M., Haber, H., Seydel, J.K., Krause, E., Bienert, M., Carpino, L.A., El-Faham, A. and Albericio, F., J. Org. Chem., 60 (1995) 405.

Wenschuh, H., Beyermann, M., Rothemund, S., Carpino, L.A. and Bienert, M., Tetrahedron Lett., 36 (1995) 1247.

Wenschuh, H., Beyermann, M., Bienert, M., El-Faham, A., Ghassemi, S. and Carpino, L.A., In Kaumaya, P.T.P. and Hodges, R.S. (Eds.) Peptides: Chemistry, Structure and Biology, Mayflower Scientific Ltd., Kingswinford, 1996, p. 33.

Wenschuh, H., Beyermann, M., El-Faham, A., Ghassemi, S., Carpino, L.A. and Bienert, M., J. Chem. Soc., Chem. Commun., (1995) 669.

Carpino, L.A., Beyermann, M., Wenschuh, H. and Bienert, M., Acc. Chem. Res., 29 (1996) 268.

Carpino, L.A., Ionescu, D., El-Faham, A., Henklein, P., Wenschuh, H., Bienert, M. and Beyermann, M., Tetrahedron Lett., 39 (1998) 241.

Wenschuh, H., Beyermann, M., Winter, R., Bienert, M., Ionescu, D. and Carpion, L.A., Tetrahedron Lett., 37 (1996) 5483.

Gopi, H.N. and Suresh Babu, V.V., Tetrahedron Lett., 39 (1998) 9769.

Henze, H.R. and Speer, R.J., J. Am. Chem. Soc., 64 (1942) 522.

Freidinger, R.M., Hinkle, J.S., Perlow, D.S. and Arison, B.H., J. Org. Chem., 48 (1983) 77.

McDermott, J.R. and Benoiton, N.L., Can. J. Chem., 51 (1973) 1915.

Cheung, S.T. and Benoiton, N.L., Can. J. Chem., 55 (1977) 906.

Kaduk, C., Wenschuh, H., Beyermann, M., Forner, K., Carpino, L.A. and Bienert, M., Lett. Pept. Sci., 2 (1995) 285.