Stabilization of a novel β-turn-like motif by nonconventional intramolecular hydrogen-bonding interactions in a model peptide incorporating β-alanine

Biopolymers

Volumn 53, Issue 6, 2000, Pages 447-454

  Thakur, A K ^a   Kishore, R ^a  

^a INSTITUTE OF MICROBIAL TECHNOLOGY   (India)

Author keywords

Ala residue; turn like structure; Nonconventional hydrogen bonding interactions

Indexed keywords

AMINO ACIDS; CONFORMATIONS; CRYSTAL STRUCTURE; CRYSTALLIZATION; HYDROGEN BONDS; MOLECULAR STRUCTURE; POLYPEPTIDES; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

BETA ALANINE;

BIOPOLYMERS;

BETA ALANINE; PEPTIDE;

ARTICLE; CRYSTAL STRUCTURE; HYDROGEN BOND; PROTEIN FOLDING; PROTEIN SECONDARY STRUCTURE; PROTEIN STABILITY; PROTEIN TERTIARY STRUCTURE; STEREOSPECIFICITY; STRUCTURE ANALYSIS;

BETA-ALANINE; HYDROGEN; MODELS, MOLECULAR; PEPTIDES; PROTEIN FOLDING;

EID: 0034052404     PISSN: 00063525     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1097-0282(200005)53:6<447::AID-BIP1>3.0.CO;2-H     Document Type: Article

References (42)

1. Karle, I. L.; Handa, B. K.; Hassal. C. H. Acta Crystallogr 1975, 31, 555-560.
2. Springer, J. P.; Cole, R. J.; Dorner, J. W.; Cox, R. H.; Richard, J. L.; Barnes, C. L.; van der Helm, D. J Am Chem Soc 1984, 106, 2388-2392.
3. Aubry, A.; Murraud, M. Biopolymers 1989, 28, 109-122.
4. Di Blasio, B.; Lombardi, A.; Yang, X.; Pedone, C.; Pavone, V. Biopolymers 1991, 31, 1181-1188.
5. Saviano, G.; Temussi, P. A.; Motta, A.; Maggi, C. A.; Rovero, P. Biochemistry 1991, 10175-10181.
6. Tormo, J.; Puiggali, J.; Vives, J.; Fila, I.; Lloveras, J.; Bella, J.; Aymami, J.; Subirana, J. A. Biopolymers 1992, 32, 643-648.
7. Pavone, V.; Di Blasio, B.; Lombardi, A.; Isernia, C.; Pedone, C.; Benedetti, E.; Valle, G.; Crisma, M.; Toniolo, C.; Kishore, R. J Chem Soc Perkin Trans II 1992, 1233-1237.
8. Bardi, R.; Piazzesi, A. M.; Crisma, M.; Toniolo, C.; Kishore, R. Zeit Krystallogr 1993, 207, 290-292.
9. Dado, G. P.; Gellman, S. H. J Am Chem Soc 1994, 116, 1054-1062.
10. Pavone, V.; Lombardi, A.; Saviano, M.; Nastri, F.; Fattorusso, R.; Maglio, O.; Isernia, C.; Paolillo, L.; Pedone, C. Biopolymers 1994, 34, 1517-1526.
11. Lombardi, A.; Saviano, M.; Nastri, F.; Fattorusso, R.; Maglio, O.; Mazzeo, M.; Pedone, C.; Isernia, C.; Pavone, V. Biopolymers 1996, 38, 683-691.
12. Kishore, R. Tetrahedron Lett 1996, 37, 5747-5750.
13. Benedetti, E. Biopolymers (Peptide Sci) 1996, 40, 3-44.
14. Karle, I. L.; Pramanik, A.; Banerjee, A.; Bhattacharjya, S.; Balaram, P. J Am Chem Soc 1997, 39, 9088-9095.
15. Wrighton, N. C.; Balasubramanian, P.; Barbone, F. P.; Kashyap, A. K.; Farrell, F. X.; Jolliffe, L. K.; Barret, R. W.; Dower, W. J. Nature Biotech 1997, 15, 1261-1265.
16. Thakur, A. K.; Kishore, R. Tetrahedron Lett 1998, 39, 9553-9556.
17. Thakur, A. K.; Kishore, R. Tetrahedron Lett 1999, 40, 5091-5094.
18. Wu, Y.-D.; Wang, D.-P. J Am Chem Soc 1998, 120, 13487-13488.
19. Sheldrick, G. M. SHELXS-86: Program for Crystal Structure Solution, University of Gottingen, Germany, 1986.
20. Sheldrick, G. M. SHELX-76: Program for Crystal Structure Determination; University of Cambridge, England, 1976.
21. Paul, P. K. C.; Sukumar, M.; Bardi, R.; Piazzesi, A. M.; Valle, G.; Toniolo, C.; Balaram, P. J Am Chem Soc 1986, 108, 6363-6370.
22. Venkatachalam, C. M. Biopolymers 1968, 6, 1425-1436.
23. Rose, G. D.; Gierasch, L. M.; Smith, J. A. Adv Protein Chem 1985, 37, 1-109.
24. Desiraju, G. R. Angew Chem Int Ed Engl 1995, 34, 2311-2327.
25. Desiraju, G. R. Acc Chem Res 1996, 29, 441-449.
26. Steiner, T. Chem Commun 1997, 727-728.
27. Taylor, R.; Kennard, O. Acc Chem Res 1984, 23, 320-326.
28. Aakeröy, C. B.; Seddom, K. R. Chem Soc Rev 1993, 397-407.
29. Philip, D.; Stoddart, J. F. Angew Chem Int Ed Engl 1996, 35, 1154-1196.
30. Steiner, T.; Desiraju, G. R. Chem Commun 1997, 891-892.
31. Desiraju, G. R. Crystal Engineering: The Design of Organic Solids; Elsevier: Amsterdam, 1989.
32. Braga, D.; Grepioni, F.; Desiraju, G. R. Chem Rev 1998, 98, 1375-1405.
33. Derewenda, Z. S.; Derewenda, U.; Kobos, P. M. J Mol Biol 1994, 241, 83-93.
34. Derewenda, Z. S.; Lee, L.: Derewenda, U. J Mol Biol 1995, 252, 248-268.
35. Bella, J.; Berman, H. M. J Mol Biol 1996, 264, 734-740.
36. Kramer, R. Z.; Vitagliano, L.; Bella, J.; Berisio, R.; Mazzarella, L.; Brodsky, B.; Zagari, A.; Berman, H. M. J Mol Biol 1998, 280, 623-638.
37. Crisma, M.; Formaggio, F.; Toniolo, C.; Yoshikawa, T.; Wakamiya, T. J Am Chem Soc 1999, 121, 3272-3278.
38. Bardi, R.; Piazzesi, A. M.; Toniolo, C.; Sukumar, M.; Raj, P. A.; Balaram, P. Int J Peptide Protein Res 1985, 25, 628-639.
39. Valle, G.; Crisma, M.; Toniolo, C.; Sen, N.; Sukumar, M.; Balaram, P. J Chem Soc Perkin Trans II 1988, 393-398.
40. Benedetti, E.; Bavoso, A.; Di Blasio, B.; Grimaldi, P.; Pavone, V.; Pedone, C.; Toniolo, C.; Bonora, G. M. Int J Macromol 1985, 7, 81-88.
41. Griffith, O. W. Ann Rev Biochem 1986, 55, 855-878.
42. Kleinkauf, H.; Von Dohren, H. Ann Rev Microbiol 1987, 41, 259-289.