Nα-Fmoc-O,O-(dimethylphospho)-L-tyrosine fluoride: A convenient building block for the solid-phase synthesis of phosphotyrosyl peptides

Letters in Peptide Science

Volumn 4, Issue 3, 1997, Pages 171-176

  Fretz, Heinz ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

Author keywords

Amino acid fluoride; Dialkyl amino acids; Peptide bond formation; TPTU

Indexed keywords

EID: 0004658473     PISSN: 09295666     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF02443530     Document Type: Article

References (30)

1. a. Toniolo, C. and Benedetti, E., Trends Biochem. Sci., 16 (1991) 350.
2. b. Toniolo, C., Crisma, M., Formaggio, F., Valle, G., Cavicchioni, G., Précigoux, G., Aubry, A. and Kamphuis, J., Biopolymers, 33 (1993) 1061.
3. c. Turk, J., Panse, G.T. and Marshall, G.R., J. Org. Chem., 40 (1975) 953.
4. d. Toniolo, C., Pantano, M., Formaggio, F., Crisma, M., Aubry, A., Bayeul, D., Précigoux, G., Dautant, A., Boesten, W.H.J., Schoemaker, H.E. and Kamphuis, J., In Hodges, R.S. and Smith, J.A. (Eds.) Peptides: Chemistry, Structure and Biology (Proceedings of the 13th American Peptide Symposium), ESCOM, Leiden, The Netherlands, 1994, pp. 315-317.
5. e. Karle, I.L., In Kaumaya, P.T.P. and Smith, J.A. (Eds.) Peptides: Chemistry, Structure and Biology (Proceedings of the 14th American Peptide Symposium), Mayflower Worldwide, Kingswinford, U.K., 1996, p. 543.
6. Fabiano, N., Valle, G., Crisma, M., Toniolo, C., Saviano, M., Lombardi, A., Isernia, C., Pavone, V., Di Blasio, B., Pedone, C. and Benedetti, E., Int. J. Pept. Protein Res., 42 (1993) 459.
7. Spencer, J.R., Antonenko, V.V., Delaet, N.G.J. and Goodman, M., Int. J. Pept. Protein Res., 40 (1992) 282.
8. a. Coste, J., Dufour, M.-N., Pantaloni, A. and Castro, B., Tetrahedron Lett., 31 (1990) 669.
9. b. Frérot, E., Coste, J., Pantaloni, A., Dufour, M.-N. and Jouin, P., Tetrahedron, 47 (1991) 259.
10. c. Coste, J., Frérot, E. and Jouin, P., J. Org. Chem., 59 (1994) 2437.
11. a. Carpino, L.A., El-Faham, A. and Albericio, F., J. Chem. Soc., Chem. Commun., (1994) 201.
12. b. Carpino, L.A., J. Am. Chem. Soc., 115 (1993) 4397.
13. Akaji, K., Tamai, Y. and Kiso, Y., Tetrahedron Lett., 36 (1995) 9341.
14. Fuller, W.D., Cohen, M.P., Shabankareh, M., Blair, R.K., Goodman, M. and Naider, F.R., J. Am. Chem. Soc., 112 (1990) 7414.
15. Wenschuh, H., Beyermann, M., Krause, E., Brudel, M., Winter, R., Schümann, M., Carpino, L.A. and Bienert, M., J. Org. Chem., 59 (1994) 3275.
16. Carpino, L.A., Sadat-Aalaee, D., Chao, H.G. and DeSeims, R.H., J. Am. Chem. Soc., 112 (1990) 9651.
17. Kaduk, C., Wenschuh, H., Beyermann, M., Forner, K., Carpino, L.A. and Bienert, M., Lett. Pept. Sci., 2 (1995) 285.
18. Carpino, L.A. and El-Faham, A., J. Am. Chem. Soc., 117 (1995) 5401.
19. Ottinger, E.A., Shekels, L.L., Bernlohr, D.A. and Barany, G., Biochemistry, 32 (1993) 4354.
20. a. Castro, B., Dormoy, J.R., Evin, G. and Selve, C., Tetrahedron Lett., 14 (1975) 1219.
21. b. García-Echeverría, C., Lett. Pept. Sci., 2 (1995) 93.
22. a. Knorr, R., Trzeciak, A., Bannwarth, W. and Gillessen, D., In Giralt, E. and Andreu, D. (Eds.) Peptides 1990 (Proceedings of the 21st European Peptide Symposium), ESCOM, Leiden, The Netherlands, 1991, p. 62.
23. b. Knorr, R., Trzeciak, A., Bannwarth, W. and Gillessen, D., Tetrahedron Lett., 30 (1989) 1927.
24. Rink, H., Tetrahedron Lett., 28 (1987) 3787.
25. Kaiser, E.T., Colescott, R.L., Bossinger, C.D. and Cock, P.I., Anal. Biochem., 54 (1970) 595.
26. Wade, J.D., Bedford, J., Sheppard, R.C. and Tregaer, G.W., Pept. Res., 4 (1991) 194.
27. Shuai, K., Stark, G.R., Kerr, I.M. and Darnell Jr., J.E., Science, 261 (1993) 1744.
28. Fretz, H., Lett. Pept. Sci., 3 (1996) 343.
29. Meutermans, W.D.F. and Alewood, P.F., Tetrahedron Lett., 37 (1996) 4765.
30. Perich, J.W, Lett. Pept. Sci., 3 (1996) 127.