Stereochemical analysis of higher α,α-dialkylglycine containing peptides. Characterization of local helical conformations at dipropylglycine residues and observation of a novel hydrated multiple β-turn structure in crystals of a glycine rich peptide

Journal of the American Chemical Society

Volumn 119, Issue 50, 1997, Pages 12048-12054

  Karle, Isabella L ^b   Kaul, Ramesh ^a,c   Rao, R Balaji ^c   Raghothama, S ^a   Balaram, P ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

^b NAVAL RESEARCH LABORATORY   (United States)

^c BANARAS HINDU UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

PEPTIDE;

ARTICLE; CONFORMATIONAL TRANSITION; CRYSTAL STRUCTURE; CRYSTALLOGRAPHY; PROTEIN ANALYSIS; PROTEIN CONFORMATION; PROTEIN STRUCTURE; RESIDUE ANALYSIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

EID: 0031576688     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja970596z     Document Type: Article

References (41)

1. Balaram, P. Curr. Opin. Struct. Biol. 1992, 2, 845-851.
2. Benedetti, E.; Toniolo, C. Polymeric Materials Encyclopedia 1996, 8, 6472-6481.
3. (a) Abbreviations used: Aib, α-aminoisobutyric acid; Deg, α,α-diethylglycine; Dpg, α,α-di-n-propylglycine; Dbg, α,α-di-n-butylglycine; Boc, tert-butyloxycarbonyl; OMe, methyl ester; OBzl, benzyl ester; NHMe, methylamide.
4. (b) IUPAC-IUB Commission on Biochemical Nomenclature. Biochemistry 1970, 9, 3471-3479.
5. Prasad, B. V. V.; Balaram, P. CRC Crit. Rev. Biochem. 1984, 16, 307-347.
6. Karle, I. L.; Balaram, P. Biochemistry 1990, 29, 6747-6756.
7. Benedetti, E.; Toniolo, C.; Hardy, P. M.; Barone, V.; Bavoso, A.; Di Blasio, B.; Grimaldi, P.; Lelj, F.; Pavone, V.; Pedone, C.; Bonora, G. M.; Lingham, I. J. Am. Chem. Soc. 1984, 106, 8146-8152.
8. Bonora, G. M.; Toniolo, C.; DiBlasio, B.; Pavone, V.; Pedone, C.; Benedetti, E.; Lingham, I.; Hardy, P. M. J. Am. Chem. Soc. 1984, 106, 8152-8156.
9. Benedetti, E.; Barone, V.; Bavoso, A.; DiBlasio, B.; Lelj, F.; Pavone, V.; Pedone, C.; Bonora, G. M.; Toniolo, C.; Leplawy, M. T.; Kaczmarek, K.; Redlinski, A. Biopolymers 1988, 27, 357-371.
10. Toniolo, C.; Benedetti. E. Macromolecules 1991, 24, 4004-4009.
11. Barone, V.; Lelj, F.; Bavoso, A.; DiBlasio, B.; Grimaldi, P.; Pavone, V.; Pedone, C. Biopolymers 1985, 24, 1759-1767.
12. DiBlasio, B.; Pavone, V.; Isernia, C.; Pedone C.; Benedetti, E.; Toniolo, C.; Hardy, P. M.; Lingham, I. J. Chem. Soc, Perkin Trans. 2 1992, 2, 523-526.
13. Karle, I. L.; Rao R. B.; Prasad, S.; Kaul, R.; Balaram, P. J. Am. Chem. Soc. 1994, 116, 10355-10361.
14. Karle, I. L.; Gurunath, R.; Prasad, S.; Kaul, R.; Rao R. B.; Balaram, P. J. Am. Chem. Soc. 1995, 117, 9632-9637.
15. Karle, I. L.; Rao R. B.; Kaul, R.; Prasad, S.; Balaram, P. Biopolymers 1996, 39, 75-84.
16. Karle, I. L.; Gurunath, R.; Prasad, S.; Rao R. B.; Balaram, P. Int. J. Peptide Protein Res. 1996, 47, 376-382.
17. Prasad S.; Mitra S.; Subramanian, E.; Velmurugan, D.; Rao, R. B.; Balaram, P. Biochem. Biophys. Res. Commun. 1994, 198, 424-430.
18. Richardson, J. S.; Richardson, D. C. In Prediction of Protein Structure and Principles of Protein Conformation. Fasman, G. D., Ed.; Plenium Press: New York, pp 1-95.
19. Karle, I. L.; Banerjee, A.; Bhattacharjya, S.; Balaram, P. Biopolymers 1996, 38, 515-526.
20. Toniolo, C.; Peggion, C.; Crisma, M.; Formaggio, F.; Shui, X.; Eggleston, D. S. Nature Struct. Biol. 1994, 1, 908-914.
21. Gurunath, R.; Balaram, P. Biopolymers 1995, 35, 21-29.
22. Monaco, V.; Formaggio, F.; Crisma, M.; Toniolo, C.; Shui, X.; Eggleston, D. S. Biopolymers 1996, 39, 31-42.
23. Prasad, S.; Rao, R. B.; Balaram, P. Biopolymers 1995, 35, 11-20.
24. Wuthrich, K. NMR of Proteins and Nucleic Acids; John Wiley and Sons: New York, 1986.
25. Kopple, K. D.; Schamper, T. J. J. Am. Chem. Soc. 1972, 94, 3644-3646.
26. Kopple, K. D.; Go, A.; Pilipauskas, D. R. J. Am. Chem. Soc. 1975, 97, 6830-6838.
27. Pitner, T. P., Urry D. W. J. Am. Chem. Soc. 1972, 94, 1399-1400.
28. Iqbal, M.; Balaram, P. J. Am. Chem. Soc. 1981, 103, 5548-5552.
29. Karle, I. L. Biopolymers 1996, 40, 157-180.
30. Schellman, C. In Protein Folding; Janenicke, R., Ed.; Elsevier/North Holland Biochemical Press: Amsterdam, 1980; pp 53-61.
31. Milner-White, E. J. J. Mol. Biol. 1988, 199, 503-511.
32. Nagarajaram, H. A.; Sowdhamini, R.; Ramakrishnan, C.; Balaram, P. FEBS Lett. 1993, 321, 79-83.
33. Aurora, R.; Srinivasan, R.; Rose, G. D. Science 1994, 264, 1126-1130.
34. Karle, I. L.; Flippen-Anderson, J. L.; Uma, K.; Balaram, P. Int. J. Pept. Protein Res. 1993, 42, 401-410.
35. Rajashankar, K. R.; Ramakumar, S.; Mal, T. K.; Jain, R. M.; Chauhan, V. S. Angew. Chem., Int. Ed. Engl. 1996, 35, 765-768.
36. Banerjee, A.; Datta, S.; Pramanik, A.; Shamala, N.; Balaram, P. J. Am. Chem. Soc. 1996, 118, 9477-9483.
37. Banerjee, A.; Raghothama, S.; Karle, I. L.; Balaram, P. Biopolymers 1996, 39, 279-285.
38. Dentino, A, R.; Raj, P. A.; Bhandary, K. K.; Wilson, M. E.; Levine, M. J. J. Biol. Chem. 1991, 266, 18460-18468.
39. Prasad, S.; Rao, R. B.; Bergstrand, H.; Lundquist, B.; Becker, E. L.; Balaram, P. Int. J. Pept. Protein Res. 1996, 48, 312-318.
40. Datta, S.; Kaul, R.; Rao, R. B.; Shamala, N.; Balaram, P. J. Chem. Soc., Perkin Trans. 2 1997, in press.
41. Crisma, M.; Valle, G.; Toniolo. C.; Rao, R. B.; Prasad, S.; Balaram, P. Biopolymers 1995, 35, 1-9.