Azaproline as a β-turn-inducer residue opposed to proline

Journal of Peptide Research

Volumn 52, Issue 1, 1998, Pages 19-26

  Zouikri, M ^a   Vicherat, A ^a   Aubry, A ^b   Marraud, M ^a   Boussard, G ^a  

^a LAB DE CHIM PHYS MACROMOLECULAIRE   (France)

^b CNRS   (France)

Author keywords

Azapeptide folding; Azapeptides; Azaproline; Pseudopeptides; VI turn

Indexed keywords

AZAPROLINE; PROLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; ENZYME INHIBITION; NONHUMAN; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN FOLDING; PROTEIN MODIFICATION; PROTON NUCLEAR MAGNETIC RESONANCE; RESIDUE ANALYSIS; STRUCTURE ANALYSIS;

EID: 0031848502     PISSN: 1397002X     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1399-3011.1998.tb00648.x     Document Type: Article

References (43)

1. Marraud, M. & Aubry, A. (1996) Biopolym. Pept. Sci. 40, 45-83
2. Gante, J. (1989) Synthesis 405-413 and references cited therein
3. Gante, J. (1994) Angew. Chem. Int. Ed. Engl. 33, 1699-1720 and references cited therein
4. Ulm, E.H., Hickens, M., Gomez, H.J., Till, A.E. & Hand, E. (1982) Clin. Pharmacol. 54, 357-362
5. Greenlee, W.J., Thorsett, E.D., Springer, J.P., Patchett, A.A., Ulm, E.H. & Vassil, T.C. (1984) Biochem. Biophys. Res. Commun. 112, 791-797
6. Gray, C.J., Al-Dulaimi, K., Khonjak, A.M. & Parker, R.C. (1977) Tetrahedron 33, 837-840
7. Powers, J.C., Boone, R., Carroll, D.L., Gupton, B.F., Kam, C.M., Nishino, N., Sukamoto, M. & Tuhy, P.M. (1984) J. Biol. Chem. 259, 4288-4294
8. Dutta, A.S., Giles, M.B. & Williams, J.C. (1986) Perkin Trans. 1 1655-1664
9. Graybill, T.L., Ross, M.J., Gauvin, B.R., Gregory, J.S., Harris, A.L., Ator, M.A., Rinker, J.M. & Dolle, R.E. (1992) Bioorg. Med. Chem. Lett. 1, 1375-1380
10. Gante, J., Krug, M., Lauterbach, G., Weitzel, R. & Hiller, W. (1995) J. Pept. Sci. 1, 201-206
11. Hess, H.J., Marchand, W.T. & Laubach, G.D. (1963) J. Am. Chem. Soc. 85, 4040-4041
12. Antsans, J.J., Makarova, N.A. & Chipens, G. (1981) Bioorg. Khim. 7, 336-341
13. Niedrich, H. (1972) J. Prakt. Chem. 314, 769-779
14. Niedrich, H. & Oehme, C. (1972) J. Prakt. Chem. 314, 759-768
15. Oehme, C., Bergmann, J., Falck, M., Reich, J.G., Voigt, W.E., Niedrich, H., Pirrwitz, J., Berseck, C. & Jung, F. (1972) Acta Biol. Med. Ger. 28, 109-131
16. Oehme, C., Bergmann, J. & Niedrich, H. (1974) J. Prakt. Chem. 316, 741-749
17. Ho, T.L., Nestor, J. J, McGrae, G.I. & Vickery, B.H. (1984) Int. J. Pept. Protein Res. 24, 79-84
18. Dutta, A.S. & Furr, B.J.A. (1985) Annu. Rep. Med. Chem. 20, 203-214
19. Furr, B.J.A., Valcaccia, B.E. & Hutchinson, F.G. (1983) Br. J. Cancer 48, 140
20. Nestor, J.J., Tahibramani, R., Ho, T.L., McGrae, G.I. & Vickery, B.H. (1988) J. Med. Chem. 31, 65-72
21. König, W., Sandow, J., Jerobek-Sandow, G. & Kolar, C. (1989) in Peptides 1988 (Jung, G. & Bayer, E. eds.), pp. 334-336, Walter de Gruyter, Berlin
22. Hutchinson, F.G. & Furr, B.J.A. (1987) Trends Biotechnol. 5, 102-106
23. Kedel, M., Diaz, J. & Cazaubon, C. (1984) CA 100, 175295, Sanofi French Patent 2523126 (1983)
24. Dutta, A.S., Gormley, J.J., Hayward, C.F., Morley, J.S., Shaw, J.S., Stacey, G.J. & Turnbull, M.T. (1977) Life Sci. 21, 559-562
25. Gacel, G., Zajac, J.M., Delay-Goyet, P., Dangé, V. & Roques, B.P. (1988) J. Med. Chem. 31, 374-383
26. Dutta, A.S. & Morley, J.S. (1975) Perkin Trans. 1 1712-1720
27. Gray, C.J., Ireson, J.C. & Parker, R.C. (1977) Tetrahedion 33, 739-743
28. Dutta, A.S., Furr B.J.A., Giles, M.B. & Morley, J.S. (1976) Clin. Endocrinol. 5, suppl., 291s-298s
29. Gray, C.J. & Parker, R.C. (1975) Tetrahedron 31, 2940-2943
30. Dutta, A.S. & Morley, J.S. (1976) in Peptides 1976 (Loffet, A., ed.), pp. 517-522, Editions de l'Université de Bruxelles, Bruxelles
31. Gray, C.J., Quibell, M., Jiang, K.L. & Baggett, N. (1991) Synthesis 141-146
32. Dutta, A.S., Furr, B.J.A., Giles, M.B., Valcaccia, B. & Walpole A.L. (1978) Biochem. Biophys. Res. Commun. 81, 382-390
33. Pinnen, F., Luisi, G., Lucente, G., Gavuzzo, E. & Cerrini, S. (1993) J. Chem. Soc. Perkin Trans 1 819-824
34. Pinnen, F., Luisi, G., Calgagni, A., Lucente, G., Gavuzzo, E. & Cerrini, S. (1994) J. Chem. Soc. Perkin Trans 1 1611-1617
35. André, F., Boussard, G., Bayeul, D., Didierjean, C., Aubry, A. & Marraud, M. (1997) J. Pept. Res. 49, 556-562
36. André, F., Vicherat, A., Boussard, G., Aubry, A. & Marraud, M. (1997) J. Pept. Res. 50, 372-381
37. Didierjean, C, Del Duca, V., Benedetti, E., Aubry, A., Zouikri, M., Marraud, M. & Boussard, G. (1997) J. Pept. Res. 50, 451-457
38. Rose, G.D., Gierasch, L.M. & Smith, J.A. (1985) Adv. Protein Chem. 37, 1-109
39. MacArthur, M.W. & Thornton J.M. (1991) J. Mol. Biol. 218, 397-412
40. Lecoq, A., Boussard, G., Marraud, M. & Aubry, A. (1993) Biopolymers 33, 1051-1059
41. André, A., Marraud, M., Tsouloufis, T, Tzartos, S.J. & Boussard, G. (1997) J. Pept. Sci. 3, 429-441
42. Aubry, A., Cung, M.T. & Marraud, M. (1985) J. Am. Chem. Soc. 107, 7640-7647
43. Boussard, G. & Marraud, M. (1985) J. Am. Chem. Soc. 107, 1825-1828