Folding of peptides characterized by c3Val, a highly constrained analogue of valine

Biopolymers

Volumn 68, Issue 2, 2003, Pages 178-191

  Peggion, Cristina ^a   Formaggio, Fernando ^a   Crisma, Marco ^a   Toniolo, Claudio ^a   Jiménez, Ana I ^b   Cativiela, Carlos ^b   Kaptein, Bernard ^c   Broxterman, Quirinus B ^c   Saviano, Michele ^d   Benedetti, Ettore ^d  

^a UNIVERSITY OF PADOVA   (Italy)

^b CSIC   (Spain)

^c DSM Fine Chemicals Austria Nfg GmbH & Co KG   (Netherlands)

^d UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

bend; 310 helix; Amino acid synthesis; C tetrasubstituted amino acids; Conformational analysis; Cyclopropane amino acid; Ir absorption; NMR; Peptide synthesis; X ray diffraction

Indexed keywords

CONFORMATIONS; FOURIER TRANSFORM INFRARED SPECTROSCOPY; PROPANE; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION;

CHIRALITY;

AMINO ACIDS;

AMINO ACID DERIVATIVE; CYCLOPROPANE; GLYCINE; VALINE;

ARTICLE; BIOSYNTHESIS; CONFORMATION; CRYSTAL STRUCTURE; ENANTIOMER; INFRARED SPECTROSCOPY; INTERMETHOD COMPARISON; METHYLATION; PROTEIN ANALYSIS; PROTEIN FOLDING; PROTEIN STRUCTURE; X RAY DIFFRACTION;

CRYSTALLOGRAPHY, X-RAY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; OLIGOPEPTIDES; PEPTIDES; PROTEIN CONFORMATION; PROTEIN FOLDING; VALINE; X-RAY DIFFRACTION;

EID: 0037322818     PISSN: 00063525     EISSN: None     Source Type: Journal    
DOI: 10.1002/bip.10295     Document Type: Article

References (72)

1. Toniolo, C.; Benedetti, E. Macromolecules 1991, 24, 4004-4009.
2. Toniolo, C.; Crisma, M.; Formaggio, F.; Peggion, C. Biopolymers (Pept Sci) 2001, 60, 396-419.
3. Toniolo, C. CRC Crit Rev Biochem 1980, 9, 1-44.
4. Venkatachalam, C. M. Biopolymers 1968, 6, 1425-1436.
5. Rose, G. D.; Gierasch, L. M.; Smith, J. A. Adv Protein Chem 1985, 37, 1-109.
6. Toniolo, C.; Benedetti, E. Trends Biochem Sci 1991, 16, 350-353.
7. Bolin, K. A.; Millhauser, G. L. Acc Chem Res 1999, 32, 1027-1033.
8. Toniolo, C.; Crisma, M.; Formaggio, F.; Valle, G.; Cavicchioni, G.; Précigoux, G.; Aubry, A.; Kamphuis, J. Biopolymers 1993, 33, 1061-1072.
9. Valle, G.; Crisma, M.; Toniolo, C.; Polinelli, S.; Boesten, W. H. J.; Schoemaker, H. E.; Meijer, E. M.; Kamphuis, J. Int J Pept Protein Res 1991, 37, 521-527.
10. Toniolo, C.; Crisma, M.; Bonora, G. M.; Klajc, B.; Lelj, F.; Grimaldi, P.; Rosa, A.; Polinelli, S.; Boesten, W. H. J.; Meijer, E. M.; Schoemaker, H. E.; Kamphuis, J. Int J Pept Protein Res 1991, 38, 242-252.
11. Formaggio, F.; Pantano, M.; Valle, G.; Crisma, M.; Bonora, G. M.; Mammi, S.; Peggion, E.; Toniolo, C.; Boesten, W. H. J.; Schoemaker, H. E.; Kamphuis, J. Macromolecules 1993, 26, 1848-1852.
12. Polese, A.; Formaggio, F.; Crisma, M.; Valle, G.; Toniolo, C.; Bonora, G. M.; Broxterman, Q. B.; Kamphuis, J. Chem Eur J 1996, 2, 1104-1111.
13. Lapeña, Y.; Lopez, P.; Cativiela, C.; Kaptein, B.; Broxterman, Q. B.; Kamphuis, J.; Mossel, E.; Peggion, C.; Formaggio, F.; Crisma, M.; Toniolo, C. J Chem Soc, Perkin Trans 2, 2000, 631-636.
14. Mossel, E.; Formaggio, F.; Valle, G.; Crisma, M.; Toniolo, C.; Doi, M.; Ishida, T.; Broxterman, Q. B.; Kamphuis, J. Lett Pept Sci 1998, 5, 223-225.
15. Toniolo, C.; Benedetti, E. In Molecular Conformation and Biological Interactions; Balaram, P., Ramaseshan, S., Eds.; Indian Academy of Sciences: Bangalore, India, 1991; pp 511-521.
16. Benedetti, E.; Di Blasio, B.; Pavone, V.; Pedone, C.; Santini, A.; Crisma, M.; Valle, G.; Toniolo, C. Biopolymers 1989, 28, 175-184.
17. Crisma, M.; Bonora, G. M.; Toniolo, C.; Barone, V.; Benedetti, E.; Di Blasio, B.; Pavone, V.; Pedone, C.; Santini, A.; Fraternali, F.; Bavoso, A.; Lelj, F. Int J Biol Macromol 1989, 11, 345-352.
18. Benedetti, E.; Di Blasio, B.; Pavone, V.; Pedone, C.; Santini, A.; Barone, V.; Fraternali, F.; Lelj, F.; Bavoso, A.; Crisma, M.; Toniolo, C. Int J Biol Macromol 1989, 11, 353-360.
19. Valle, G.; Crisma, M.; Toniolo, C.; Holt, E. M.; Tamura, M.; Bland, J.; Stammer, C. H. Int J Pept Protein Res 1989, 34, 56-65.
20. Barone, V.; Fraternali, F.; Cristinziano, P. L.; Lelj, F.; Rosa, A. Biopolymers 1988, 26, 1673-1685.
21. Balaji, V. N.; Ramnarayan, K.; Chan, M. F.; Rao, S. N. Pept Res 1994, 7, 60-71.
22. Aleman, C. J Phys Chem 1997, B101, 5046-5050.
23. Aleman, C.; Casanovas, J.; Galembeck, S. E. J Comput-Aided Mol Design 1998, 12, 259-273.
24. Varughese, K. I.; Srinivasan, A. R.; Stammer, C. H. Int J Pept Protein Res 1985, 26, 242-251.
25. Mapelli, C.; Elrod, L. F.; Switzer, F. L.; Stammer, C. H.; Holt, E. M. Biopolymers 1989, 28, 123-128.
26. Burgess, K.; Ho, K.-K.; Pettitt, B. M. J Am Chem Soc 1995, 117, 54-65.
27. Burgess, K.; Ho, K.-K.; Pal, B. J Am Chem Soc 1995, 117, 3808-3819.
28. Burgess, K.; Ke, C.-Y. J Org Chem 1996, 61, 8627-8631.
29. Burgess, K.; Ke, C.-Y. J Pept Res 1997, 49, 201-209.
30. Burgess, K.; Li, W.; Lim, D.; Moye-Sherman, D. Biopolymers 1997, 42, 439-453.
31. Burgess, K.; Lim, D. J Am Chem Soc 1997, 119, 9632-9640.
32. Moye-Sherman, D.; Jin, S.; Li, S.; Welch, M. B.; Reibenspies, J.; Burgess, K. Chem Eur J 1999, 5, 2730-2739.
33. Jiménez, A. I.; Vanderesse, R.; Marraud, M.; Aubry, A.; Cativiela, C. Tetrahedron Lett 1997, 38, 7559-7562.
34. Jiménez, A. I.; Cativiela, C.; Aubry, A.; Marraud, M. J Am Chem Soc 1998, 120, 9452-9459.
35. Sheldrick, G. M. In SHELXS 97. Program for the Solution of Crystal Structures; University of Göttingen: Göttingen, Germany, 1997.
36. Sheldrick, G. M. In SHELXL 97. Program for the Refinement of Crystal Structures; University of Göttingen: Göttingen, Germany, 1997.
37. Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; Moliterni, A. G. G.; Polidori, G. In SIR 97. A Program for the Automatic Solution and Refinement of Crystal Structures; University of Bari: Bari, Italy, 1997.
38. Cromer, D. T.; Waber, J. T. In International Tables for X-Ray Crystallography, Vol. IV, Table 2.2 B; Kynoch Press:, Birmingham, UK (now distributed by D. Reidel Publ. Co.).
39. Ramage, G. R.; Simonsen, J. L. J Chem Soc 1935, 532-533.
40. Cativiela, C.; Díaz-de-Villegas, M. D.; Jiménez, A. I. Tetrahedron: Asymmetry 1995, 6, 177-182.
41. Moroder, L.; Hallet, A.; Wünsch, E.; Keller, O.; Wersin, G.; Hoppe-Seyler's Z Physiol Chem 1976, 357, 1651-1653.
42. Burk, M. J.; Allen, J. G. J Org Chem 1997, 62, 7054-7057.
43. Minguillón, C.; Franco, P.; Oliveros, L.; López, P. J Chromatogr A 1996, 728, 407-414.
44. Easton, C. J.; Fryer, N. L.; Ivory, A. J.; Tiekink, E. R. T. J Chem Soc, Perkin Trans 1, 1998, 3725-3729.
45. Chinchilla, R.; Nájera, C.; García-Granda, S.; Menéndez-Velázquez, A. Tetrahedron Lett 1993, 34, 5799-5802.
46. Kruizinga, W. H.; Bolster, J.; Kellogg, R. M.; Kamphuis, J.; Boesten, W. H. J.; Meijer, E. M.; Schoemaker, H. E. J Org Chem 1988, 53, 1826-1827.
47. Kaptein, B.; Boesten, W. H. J.; Broxterman, Q. B.; Peters, P. J. H.; Schoemaker, H. E.; Kamphuis, J. Tetrahedron: Asymmetry 1993, 4, 1113-1116.
48. Carpino, L. A. J Am Chem Soc 1993, 115, 4397-4398.
49. Leplawy, M. T.; Jones, D. S.; Kenner, G. W.; Sheppard, R. C. Tetrahedron 1960, 11, 39-51.
50. Valle, G.; Formaggio, F.; Crisma, M.; Bonora, G. M.; Toniolo, C.; Bavoso, A.; Benedetti, E.; Di Blasio, B.; Pavone, V.; Pedone, C. J Chem Soc, Perkin Trans II, 1986, 1371-1376.
51. Schröder, E.; Lübke, K. Liebigs Ann Chem 1962, 655, 211-218.
52. Toniolo, C.; Valle, G.; Bonora, G. M.; Crisma, M.; Formaggio, F.; Bavoso, A.; Benedetti, E.; Di Blasio, B.; Pavone, V.; Pedone, C. Biopolymers 1986, 25, 2237-2253.
53. Cung, M. T.; Marraud, M.; Neél, J. Ann Chim 1972, 183-209.
54. Bonora, G. M.; Mapelli, C.; Toniolo, C.; Wilkening, R. R.; Stevens, E. S. Int J Biol Macromol 1984, 6, 179-188.
55. Némethy, G.; Printz, M. P. Macromolecules 1972, 5, 755-758.
56. Kopple, K. D.; Ohnishi, M.; Go, A. Biochemistry 1969, 8, 4087-4095.
57. Martin, D.; Hauthal, H. G. In Dimethyl Sulphoxide; van Nostrand-Reinhold: Wokingham, England, 1975.
58. Kopple, K. D.; Schamper, T. J. J Am Chem Soc 1972, 94, 3644-3646.
59. IUPAC-IUB Commission for Biochemical Nomenclature, Biochemistry 1970, 9, 3471-3479.
60. Benedetti, E.; Pedone, C.; Toniolo, C.; Némethy, G.; Pottle, M. S.; Scheraga, H. A. Int J Pept Protein Res 1980, 16, 156-172.
61. Schweizer, W. B.; Dunitz, J. D. Helv Chim Acta 1982, 65, 1547-1554.
62. Benedetti, E. In Chemistry and Biochemistry of Amino Acids, Peptides and Proteins; Vol. 6; Weinstein, B., Ed.; Dekker: New York, 1982; pp 105-184.
63. Ashida, T.; Tsunogae, Y.; Tanaka, I.; Yamane, T. Acta Crystallogr 1987, B43, 212-218.
64. Paterson, Y.; Rumsey, S. M.; Benedetti, E.; Némethy, G.; Scheraga, H. A. J Am Chem Soc 1981, 103, 2947-2955.
65. Valle, G.; Crisma, M.; Formaggio, F.; Toniolo, C.; Jung, G. Liebigs Ann 1987, 1055-1060.
66. Zimmerman, S. S.; Pottle, M. S.; Némethy, G.; Scheraga, H. A. Macromolecules 1977, 10, 1-9.
67. Ramakrishnan, C.; Prasad, N. Int J Protein Res 1971, 3, 209-231.
68. Taylor, R.; Kennard, O.; Versichel, W. Acta Crystallogr 1984, B40, 280-288.
69. Görbitz, C. H. Acta Crystallogr 1989, B45, 390-395.
70. Dunitz, J. D.; Strickler, P. In Structural Chemistry and Molecular Biology; Rich, A., Davidson, N., Eds.; Freeman: San Francisco, 1968; pp 595-602.
71. Marshall, G. R. In Intra-Science Chemistry Report; Kharasch, N., Ed.; Gordon & Breach: New York, 1971; pp 305-316.
72. Karle, I. L.; Balaram, P. Biochemistry 1990, 29, 6747-6756.