Cyclopropane analogue of valine: Influence of side chain orientation on peptide folding

Tetrahedron Letters

Volumn 44, Issue 15, 2003, Pages 3147-3150

  Jiménez, Ana I ^a   Marraud, Michel ^b   Cativiela, Carlos ^a  

^a CSIC   (Spain)

^b LAB DE CHIM PHYS MACROMOLECULAIRE   (France)

Author keywords

2,3 methanovaline; Beta turn; Constrained amino acid; Crystal structure; Cyclopropane amino acid; Gamma turn; Peptide conformation; Peptide structure; Peptide turn; X ray diffraction

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; CYCLOPROPANE DERIVATIVE; DIPEPTIDE; HYDROGEN; PEPTIDE DERIVATIVE; VALINE;

ARTICLE; CRYSTAL STRUCTURE; DRUG SYNTHESIS; HYDROGEN BOND; PROTEIN FOLDING; SOLID STATE;

EID: 0037424781     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00514-8     Document Type: Article

References (24)

1. Venkatraman J., Shankaramma S.C., Balaram P. Chem. Rev. 101:2001;3131-3152.
2. Toniolo C., Crisma M., Formaggio F., Peggion C. Biopolymers. 60:2001;396-419.
3. Hill D.J., Mio M.J., Prince R.B., Hughes T.S., Moore J.S. Chem. Rev. 101:2001;3893-4011.
4. Hruby V.J. Acc. Chem. Res. 34:2001;389-397.
5. Hruby V.J., Li G., Haskell-Luevano C., Shenderovich M. Biopolymers. 43:1997;219-266.
6. Chakrabarti P., Pal D. Prog. Biophys. Mol. Biol. 76:2001;1-102.
7. Jiménez A.I., Vanderesse R., Marraud M., Aubry A., Cativiela C. Tetrahedron Lett. 38:1997;7559-7562.
8. Jiménez A.I., Cativiela C., Aubry A., Marraud M. J. Am. Chem. Soc. 120:1998;9452-9459.
9. Jiménez A.I., Cativiela C., Marraud M. Tetrahedron Lett. 41:2000;5353-5356.
10. Moye-Sherman D., Jin S., Ham I., Lim D., Scholtz J.M., Burgess K. J. Am. Chem. Soc. 120:1998;9435-9443.
11. Burgess K., Ho K.-K., Pal B. J. Am. Chem. Soc. 117:1995;3808-3819.
12. Lim D., Burgess K. J. Am. Chem. Soc. 119:1997;9632-9640.
13. Ramage G.R., Simonsen J.L. J. Chem. Soc. 1935;532-535.
14. Burk M.J., Allen J.G. J. Org. Chem. 62:1997;7054-7057.
15. Bodanszky M., Bodanszky A. The Practice of Peptide Synthesis. 1994;Springer-Verlag, Berlin.
16. Rose G.D., Gierasch L.M., Smith J.A. Adv. Protein Chem. 37:1985;1-109.
17. Aubry A., Cung M.T., Marraud M. J. Am. Chem. Soc. 107:1985;7640-7647.
18. Marraud M., Aubry A. Biopolymers. 40:1996;45-83.
19. Némethy G., Printz M.P. Macromolecules. 5:1972;755-758.
20. Benedetti E. Biopolymers. 40:1996;3-44.
21. Rizo J., Dhingra M.M., Gierasch L.M. Balaram P., Ramaseshan S. Molecular Conformation and Biological Interactions. 1991;469-496 Indian Academy of Sciences, Bangalore.
22. Alemán C., Jiménez A.I., Cativiela C., Pérez J.J., Casanovas J. J. Phys. Chem. B. 106:2002;11849-11858.
23. Alemán C., Casanovas J., Galembeck S.E. J. Comput. Aided Mol. Design. 12:1998;259-273.
24. Gómez-Catalán J., Alemán C., Pérez J.J. Theor. Chem. Acc. 103:2000;380-389.