Nonstandard Amino Acids in Conformational Design of Peptides. Helical Structures in Crystals of 5-10 Residue Peptides Containing Dipropylglycine and Dibutylglycine

Journal of the American Chemical Society

Volumn 116, Issue 23, 1994, Pages 10355-10361

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

^a NAVAL RESEARCH LABORATORY   (United States)

^b BANARAS HINDU UNIVERSITY   (India)

^c INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; DIBUTYLGLYCINE; DIPROPYLGLYCINE; PEPTIDE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; PROTEIN STRUCTURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0028073648     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00102a001     Document Type: Article

References (40)

1. Toniolo, C. Int. J. Pept. Protein Res. 1990, 35, 287-300.
2. Hruby, V.J.; Al-Obeidi, F.; Kazmierski, W.M. Biochem. J. 1990, 268, 249-262.
3. Balaram, P. Curr. Opin. Struct. Biol. 1992 2, 845-851.
4. Balaram, P. Pure Appl. Chem. 1992, 64, 1061-1066.
5. Karle, I.L.; Flippen-Anderson, J.L.; Sukumar, M.; Uma, K.; Balaram, P. J. Am. Chem. Soc. 1991, 113, 3952-3956.
6. Toniolo, C.; Bonora, G.M.; Bavoso, A.; Benedetti, E.; di Blasio, B.; Pavone, V.; Pedone, C. Biopolymers 1983, 22, 205-215.
7. Prasad, B.V.V.; Balaram, P. CRC Crit. Rev. Biochem. 1984, 16, 307-347.
8. Karle, I.L.; Balaram, P. Biochemistry 1990, 29, 6747-6756.
9. Di Blasio, B. ; Pavone, V.; Saviano, M.; Lombardi, A.; Nastri, F.; Pedone, C.; Benedetti, E.; Crisma, M.; Anzolin, M.; Toniolo, C. J. Am. Chem. Soc. 1992, 114, 6273-6278.
10. Karle, I.L.; Flippen-Anderson, J.L.; Uma, K.; Balaram, P. Proc. Natl. Acad. Sci. U.S.A. 1990, 87, 7921-7925.
11. Fox, R.O.; Richards, F.M. Nature 1982, 300, 325-330.
12. Karle, I.L.; Flippen-Anderson, J.L.; Agarwalla, S.; Balaram, P. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 5307-5311.
13. Karle, I.L.; Flippen-Anderson, J.L.; Agarwalla, S.; Balaram, P. Protein Struct. Fund. Sarma, R.H., Sarma, M.H., Eds. 1992, 2, 97-111.
14. Agarwalla, S.; Mellor, I.R.; Sansom, M.S.P.; Karle, I.L.; Flippen-Anderson, J.L.; Uma, K.; Krishna, K.; Sukumar, M.; Balaram, P. Biochem. Biophys. Res. Commun. 1992, 186, 8-15.
15. Bardi, R.; Piazzessi, A.M.; Toniolo, C.; Sukumar, M.; Raj, P.A.; Balaram, P. Int. J. Pept. Protein Res. 1985, 25, 628-639.
16. Paul, P.K.C.; Sukumar, M.; Bardi, R.; Piazzessi, A.M.; Valle, G.; Toniolo, C.; Balaram, P. J. Am. Chem. Soc. 1986, 108, 6363-6370.
17. Pavone, V.; Benedetti, E.; Barone, V.; di Blasio, B.; Lelj, F.; Pedone, C.; Santini, A.; Crisma, M.; Bonora, G.M.; Toniolo, C. Macromolecules 1988, 21, 2064-2070.
18. Valle, G.; Crisma, M.; Toniolo, C.; Sen. N.; Sukumar, M.; Balaram, P. J. Chem. Soc., Perkin Trans. 2 1988, 393-398.
19. Di Blasio, B.; Lombardi, A.; Nastri, F.; Saviano, M.; Pedone, C.; Yamada, T.; Nakao, M.; Kuwara, S.; Pavone, V. Biopolymers 1992, 32, 1155-1161.
20. Bardi, R.; Piazzessi, A.M.; Toniolo, C.; Sukumar, M.; Balaram, P. Biopolymers 1986, 25, 1635-1644.
21. Santini, A.; Barone, V.; Bavoso, A.; Benedetti, E.; Di Blasio, B.; Fratemali, F.; Lelj, F.; Pavone, V.; Pedone, C.; Crisma, M.; Bonora, G.M.; Toniolo, C. Int. J. Biol. Macromol. 1988, 10, 292-299.
22. Crisma, M.; Bonora, G.M.; Toniolo, C; Benedetti, E.; Bavoso, A.; Di Blasio, B.; Pavone, V.; Pedone, C. Int. J. Biol. Macromol. 1988, 10, 300-304.
23. Valle, G.; Crisma, M.; Toniolo, C. Can. J. Chem. 1988, 66, 2575-2582.
24. Crisma, M.; Bonora, G.M.; Toniolo, C.; Barone, V.; Benedetti, E.; Di Blasio, B.; Pavone, V.; Pedone, C.; Santini, A.; Fratemali, F.; Bavoso, A.; Lelj, F. Int. J. Biol. Macromol. 1989, 11, 345-352.
25. Benedetti, E.; Di Blasio, B.; Pavone, V.; Pedone, C.; Santini, A.; Barone, V.; Fratemalli, F.; Lelj, F.; Bavoso, A.; Crisma, M.; Toniolo, C. Int. J. Biol. Macromol. 1989, 11, 353-358.
26. Valle, G.; Crisma, M.; Toniolo, C.; Sudhanand; B.; Rao, R.; Sukumar, M.; Balaram, P. Int. J. Pept. Protein Res. 1991, 38, 511-518.
27. Benedetti, E.; Toniolo, C.; Hardy, P.; Barone, V.; Bavoso, A.; Di Blasio, B.; Grimaldi, P.; Lelj, F.; Pavone, V.; Pedone, C.; Borona, G.M.; Lingham, I. J. Am. Chem. Soc. 1984, 106, 8146-8152.
28. Barone, V.; Lelj, F.; Bavoso, A.; Di Blasio, B.; Grimaldi, P.; Pavone, V.; Pedone, C. Biopolymers 1985, 24, 1759-1767.
29. Benedetti, E.; Barone, V.; Bavoso, A.; Di Blasio, B.; Lelj, F.; Pavone, V.; Pedone, C.; Bonora, G.M.; Toniolo, C.; Leplawy, M.T.; Kaczmarek, K.; Redlinski, A. Biopolymers 1988, 27, 357-371.
30. Bonora, G.M.; Toniolo, C.; Di Blasio, B.; Pavone, V.; Pedone, C.; Benedetti, E.; Lingham, I.; Hardy, P. J. Am. Chem. Soc. 1984, 106, 8152-8156.
31. Toniolo, C.; Bonora, G.M.; Bavoso, A.; Benedetti, E.; Di Blasio, E.; Pavone, V.; Pedone, C.; Barone, V.; Lelj, F.; Leplawy, M.T.; Kaczmarek, K.; Redlinski, A. Biopolymers 1988, 27, 373-379.
32. Dentino, A.R.; Raj, P.A.; Bhandary, K.K.; Wilson, M.E.; Levine, M.J. J. Biol. Chem. 1991, 266, 18460-18468.
33. Di Blasio, B.; Pavone, V.; Isemia, C.; Pedone, C.; Benedetti, E.; Toniolo, C.; Hardy, P.M.; Lingham, I. J. Chem. Soc., Perkin Trans. 1992, 523-526.
34. Prasad, S.; Mitra, S.; Subramanian, E.; Velmurugan, D.; Balaji Rao, R.; Balaram, P. Biochem. Biophys. Res. Commun., in press.
35. Balaram, H.; Sukumar, M.; Balaram, P. Biopolymers 1986, 25, 2209-2223.
36. Egert, E.; Sheldrick, G.M. Acta Crystallogr. 1985, A41, 262-268.
37. Toniolo, C.; Bonora, G.M.; Bavoso, A.; Benedetti, E.; Di Blasio, D.; Pavone, V.; Pedone, C. J. Biomol. Struct. Dynam. 1985, 3, 518-526.
38. Karle, I.L.; Flippen-Anderson, J.L.; Sukumar, M.; Balaram, P. Int. J. Pept. Protein Res. 1990, 35, 518-526.
39. Karle, I.L.; Flippen-Anderson, J.L.; Uma, K.; Balaram, P. Biopolymers 1990, 29, 1835-1845.
40. Karle, I.L. Acta Crystallogr. 1992, B48, 341-356.