New mild acid-labile protecting groups for the guanidino function of N(α)-fluorenylmethoxycarbonyl-L-arginine in solid-phase peptide synthesis: 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl, 2-methoxy-10,11-dihydoro-5H- dibenzo[a,d]cyclohepten-5-yl and 5H-dibenzo[a,d]cyclohepten-5-yl groups

Journal of Peptide Research

Volumn 50, Issue 5, 1997, Pages 329-335

  Noda, Masaki ^a   Kiffe, Michael ^a  

^a SHIMADZU CORPORATION   (Japan)

Author keywords

5 dibenzosuberenyl group; 5 dibenzosuberyl group; Fmoc solid phase peptide synthesis; Protecting groups for the guanidino function of arginine; Tryptophan containing peptides

Indexed keywords

ARGININE DERIVATIVE; GUANIDINE DERIVATIVE; HEXAPEPTIDE; TRIFLUOROACETIC ACID;

ARTICLE; DERIVATIZATION; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN ASSEMBLY; PROTEIN STABILITY;

OXY;

EID: 0030840143     PISSN: 1397002X     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1399-3011.1997.tb01191.x     Document Type: Article

References (37)

1. Atherton, E. & Sheppard, R. C. (1989) Solid Phase Peptide Synthesis: A Practical Approach, IRL Press, Oxford
2. Carpino, L.A. & Han, G.Y. (1970) J. Am. Chem. Soc. 92, 5748-5749
3. Carpino, L.A. & Han, G.Y. (1972) J. Org. Chem. 37, 3404-3409
4. Carpino, L. . (1973) Acct. Chem. Res. 6, 191-198
5. Atherton, E. & Sheppard, R.C. (1987) in The Peptide, Analysis, Synthesis, Biology (Udenfriend, S., Meinhofer, J., eds.), vol. 9, p.1, Academic Press, New York
6. Wang, S.S. (1973) J. Am. Chem. Soc. 95, 1328-1333
7. Atherton, E., Fox, H., Harkiss, D., Logan, C.J., Sheppard, R.C. & Williams, B.J. (1978) J. Chem. Soc. Chem. Commun. 537-539
8. Meienhofer, J., Waki, M., Heimer, D.P., Lambros, T.J., Makofske, R.C. & Chang, C.D. (1979) Int. J. Pept. Protein Res. 13, 35-42
9. Sheppard, R.C. & Williams, B.J.(1982) Int. J. Pept. Protein Res. 20, 451-454
10. Ramage, R., Barron, C.A., Bielecki, S. & Thomas, D.W.(1987) Tetrahedron Lett. 28, 4105-4108
11. Mullen, D.G. & Barany, G. (1988) J. Org. Chem. 53, 5240-5248
12. Fujino, M., Wakimasu, M. & Kitada, C. (1981) Chem. Pharm. Bull. 29, 2825-2832
13. Ramage, R. & Green, J. (1987) Tetrahedron Lett. 28, 2287-2290
14. Green, J., Ogunjobi, O., Ramage, R. & Stewart, A.S.J. (1988) Tetrahedron Lett. 29, 4341-4344
15. Ramage, R., Green, J. & Blake, A.J. (1991) Tetrahedron 47, 6353-6370
16. Carpino, L.A., Shroff, H., Triolo, S.A., Mansour, El.M.E., Wenschuh, H. & Albericio, F. (1993) Tetrahedron Lett. 34, 7829-7832
17. King, D.G., Fields, C.G. & Fields, G.B.(1990) Int. J. Pept. Protein Res. 36, 255-266 and references cited therein
18. Sieber, P. (1987) Tetrahedron Lett. 28, 1637-1640
19. Field, G.B. & Noble, R.L.(1990) Int J. Pept. Protein Res. 35, 161-214
20. Atherton, E., Sheppard, R.C. & Wade, J.D.(1983) J. Chem. Soc. Chem. Commun. 1060-1062
21. Fields, C.G. & Fields, G .B.(1993) Tetrahedron Lett. 34, 6661-6664
22. Noda, M., Yamaguchi, M., Ando, E., Takeda, K. & Nokihara, K. (1994) J. Org. Chem.26, 7968-7975
23. Ramage, R., Irving, S.L. & McInnes, C. (1993) Tetrahedron Lett. 34, 6599-6602
24. Press, J. (1976) Helv. Chim. Acta 59, 499-512
25. Caciagli, V. & Verdini, A.S.(1988) in Peptide Chemistry (Shiba, T., Sakakibara, S., eds.), pp. 283-286, Protein Research Foundation, Osaka
26. Albericio, F., Kneib-Cordonier, N., Biancalana, S., Gera, L., Masada, R.I., Hudoson, D.& Barany, G. (1990) J. Org. Chem. 55, 3730-3743 and references cited therein
27. Stierandova, A., Sepetov, N.F., Nikiforovich, G.V. & Lebel, M.(1994) Int. J. Pept. Protein Res. 43, 31-38
28. Sole, N.A. & Barany, G. (1992) J. Org. Chem. 57, 5399-5403
29. Coste, J., Le-Nguyen, D. & Castro, B. (1990) Tetrahedron Lett. 31, 205-208
30. Bodanszky, M. & Sheehan, J.T. (1960) Chem. Ind. (Lond.) 1268-1269
31. Zervas, L., Otani, T.T., Winitz, M. & Greenstein, J.P. (1959) J. Am. Chem. Soc. 81, 2878-2884
32. Paul, R.R., Anderson, G.W. & Callahan, F.M. (1961) J. Org. Chem. 26, 3347-3350
33. Ritel, W.R. (1962) Helv. Chim. Acta 45, 2465-2473
34. Bayer, E., Gil-Av, E., Koning, A. W., Nakaparksin, S., Oro, J. & Parr, W. (1970) J. Am. Chem. Soc. 92, 1735-1738
35. White, P.(1992) in Peptides, Chemistry and Biology, Proceedings of the 12th American Peptide Symposium (Smith, J.A., Rivier, J.E., eds.), pp. 537-538, Escom, Leiden
36. Riniker, B. & Hartmann, A.(1990) in Peptides: Chemistry, Structure and Biology, Proceedings of the 11 th American Peptide Symposium (Rivier, J.E., Marshall, G.R., eds.), pp. 950-952, Escom, Leiden
37. Rink, H., Sieber, P. & Rashdorf, F. (1984) Tetrahedron Lett. 25, 621-624