β-Turn induction by C60-based fulleroproline: Synthesis and conformational characterization of Fpr/Pro small peptides

Journal of Peptide Research

Volumn 50, Issue 3, 1997, Pages 159-170

  Bianco, A ^a   Bertolini, T ^a   Crisma, M ^a   Valle, G ^a   Toniolo, C ^a   Maggini, M ^a   Scorrano, G ^a   Prato, M ^b  

^a UNIVERSITY OF PADOVA   (Italy)

^b UNIVERSITY OF TRIESTE   (Italy)

Author keywords

Conformational analysis; Crystal state conformation; Fulleroproline peptides; Infrared absorption; Nuclear magnetic resonance; Proline peptides; X ray diffraction; turns

Indexed keywords

PROLINE DERIVATIVE; SYNTHETIC PEPTIDE;

AMINO ACID ANALYSIS; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; MOLECULAR MODEL; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY DIFFRACTION;

EID: 0030865885     PISSN: 1397002X     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1399-3011.1997.tb01181.x     Document Type: Article

References (47)

1. Maggini, M., Scorrano, G., Bianco, A., Toniolo, C., Sijbesma, R.P., Wudl, F. & Prato, M. (1994) J. Chem. Soc., Chem. Commun. 305-306
2. Bianco, A., Maggini, M., Scorrano, G., Toniolo, C., Marconi, G., Villani, C. & Prato, M. (1996) J. Am. Chem. Soc. 118, 4072-4080
3. Holmes, A.B. & Stephenson, G.R. (1994) Chem. Ind. 303
4. Friedman, S.H., De Camp, D.L., Sijbesma, R.P., Srdanov, G., Wudl, F. & Kenyon, G.L. (1993) J. Am. Chem. Soc. 115, 6506-6509
5. Toniolo, C., Bianco, A., Maggini, M., Scorrano, G., Prato, M., Marastoni, M., Tomatis, R., Spisani, S., Palù, G. & Blair, E.D. (1994) J. Med. Chem. 37, 4558-4562
6. Magaard, V.W., Sanchez, R.M., Bean, J.W. & Moore, M.L. (1993) Tetrahedron Lett. 34, 381-385
7. Beausoleil, E. & Lubell, W.D. (1986) J. Am. Chem. Soc. 118, 12902-12908
8. Yaron, A. & Naider, F. (1993) CRC Crit. Rev. Biochem. 28, 31-81
9. Williams, K.A. & Deber, C.A. (1991) Biochemistry 30, 8919-8923
10. Venkatachalam, C.M. (1968) Biopolymers 6, 1425-1436
11. Toniolo, C. (1980) CRC Crit. Rev. Biochem. 9, 1-44
12. Rose, G.D., Gierasch L.M. & Smith, J.A. (1985) Adv. Protein Chem. 37, 1-109
13. Aubry, A., Protas, J., Boussard, G. & Marraud, M. (1977) Acta Crystallogr., Sect.B 33, 2399-2406
14. Boussard, G. & Marraud, M. (1985) J. Am. Chem. Soc. 107, 1825-1828
15. Liang, G., Rito, C.J. & Gellman, S.H. (1992) Biopolymers 32, 293-301
16. Boussard, G., Marraud, M. & Aubry, A. (1979) Biopolymers 18, 1297-1331
17. Aubry, A., Cung, M.T. & Marraud, M. (1985) J. Am. Chem. Soc. 107, 7640-7647
18. Bardi, R., Piazzesi, A.M., Toniolo, C., Sen, N., Balaram, H. & Balaram, P. (1988)Acta Crystallogr., Sect.C 44, 1972-1976
19. Landis, C.R., Luck, L.L. & Wright, J.M. (1995) J. Magn. Reson. B109, 44-59
20. McDonald, D.Q. & Still, W.C. (1996) J. Org. Chem. 61, 1385-1391
21. Polglase, W.J. & Smith, E L. (1949) J. Am. Chem. Soc. 71, 3081-3084
22. Berger, A., Kurtz, J. & Katchalski, E. (1954) J. Am. Chem. Soc. 76, 5552-5554
23. Weinstein, B. & Pritchard, A.E. (1972) J. Chem. Soc., Perkin Trans. 1 1015-1020
24. Nieto, M. & Perkins, H.R. (1971) Biochem. J. 123, 789-803
25. Maggini, M., Scorrano, G. & Prato, M. (1993) J. Am. Chem. Soc. 115, 9798-9799
26. Baldwin, J.E., Adlington, R.M., O'Neil, I.A., Schofield, C., Spivey, A.C. & Sweeney, J.B. (1989) J. Chem. Soc., Chem. Commun. 1852-1854
27. Sheldrick, G.M. (1976) in SHELX 76. Program for Crystal Structure Determination, University of Cambridge, U.K.
28. Sheldrick, G.M. (1985) in Crystallographic Computing 3 (Sheldrick, G.M., Kruger, C., Goddard, R., eds.), pp. 175-189, Oxford University Press, Oxford, U.K.
29. Carpino, L.A. (1993) J. Am. Chem. Soc. 15, 4397-4398
30. IUPAC-IUB Commission on Biochemical Nomenclature (1970) Biochemistry 9, 3471-3479
31. Benedetti, E., Pedone, C., Toniolo, C., Dudek, M., Némethy, G. & Scheraga, H.A. (1983) Int. J. Pept. Protein Res. 21, 163-181
32. Chakrabarti, P. & Dunitz, J.D. (1982) Helv. Chim. Acta 65, 1555-1562
33. Schweizer, W.B. & Dunitz, J.D. (1982) Helv. Chim. Acta 65, 1547-1554
34. Benedetti, E. (1982) in Chemistry and Biochemistry of Amino Acids, Peptides and Proteins (Weinstein, B., ed.), vol. VI, pp. 105-184, Dekker, New York
35. Ashida, T., Tsunogae, Y., Tanaka, I. & Yamane, T. (1987) Acta Crystallogr., Sect.B 43, 212-218
36. Ramakrishnan, C. & Prasad, B.V. (1971) Int. J. Pept. Protein Res. 3, 209-231
37. Taylor, R., Kennard, O. & Versichel, W. (1984) Acta Crystallogr., Sect.B 40, 280-288
38. Gorbitz, C.H. (1989) Acta Crystallogr., Sect.B 45, 390-395
39. Ashida, T. & Kakudo, M. (1974) Bull. Chem. Soc. Jpn. 47, 1129-1133
40. Cremer, D. & Pople, J.A. (1975) J. Am. Chem. Soc. 97, 1354-1358
41. Martin, D. & Hauthal, G. (1975) Dimethyl Sulphoxide, Van Nostrand Reinhold, Wokingham, U.K.
42. Mizushima, S., Shimanouchi, T., Tsuboi, M. & Souda, R. (1952) J. Am. Chem. Soc. 74, 270-271
43. Palumbo, M., Da Rin, S., Bonora, G.M. & Toniolo, C. (1976) Makromol. Chem. 177, 1477-1492
44. Pitner, T.P. & Urry, D.W. (1972) J. Am. Chem. Soc. 94, 1399-1400
45. Kopple, K.D., Ohnishi, M. & Go, A. (1969) Biochemistry 8, 4087-4095
46. Bothner-By, A.A. (1979) in Magnetic Resonance in Biology (Shulman, R.G., ed.), pp. 177-219, Academic Press, New York
47. Rao, B.N.N., Kumar, A., Balaram, H., Ravi, A. & Balaram, P. (1983) J. Am. Chem. Soc. 105, 7423-7428