Aromatic-aromatic interactions in crystal structures of helical peptide scaffolds containing projecting phenylalanine phenylalanine residues

Journal of the American Chemical Society

Volumn 125, Issue 18, 2003, Pages 5308-5315

  Aravinda, Subrayashastry ^a   Shamala, Narayanaswamy ^a   Das, Chittaranjan ^a   Sriranjini, Arumugam ^a   Karle, Isabella L ^b   Balaram, Padmanabhan ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

^b NAVAL RESEARCH LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC HYDROCARBONS; CONFORMATIONS; POLYPEPTIDES;

INTERMOLECULAR AROMATIC INTERACTIONS;

CRYSTAL STRUCTURE;

N TERT BUTYLOXYCARBONYLVALYLALANYLPHENYLALANYLVALYLALANYLPHENYLALANYLAMINOISOBUTYRIC ACID O METHYL ESTER; PHENYLALANINE; SYNTHETIC PEPTIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL INTERACTION; CRYSTAL STRUCTURE; ELECTRIC POTENTIAL; ENERGY TRANSFER; MOLECULAR INTERACTION; PEPTIDE ANALYSIS; PROTEIN CONFORMATION; SOLID STATE; STRUCTURE ANALYSIS; X RAY DIFFRACTION;

CRYSTALLOGRAPHY, X-RAY; MODELS, MOLECULAR; OLIGOPEPTIDES; PHENYLALANINE; PROTEIN STRUCTURE, SECONDARY;

EID: 0038631832     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0341283     Document Type: Article

References (64)

1. Burley, S. K.; Petsko, G. A. Science 1985, 229, 23-28.
2. Singh, J.; Thornton, J. M. FEBS Lett. 1985, 191, 1-6.
3. Burley, S. K.; Petsko, G. A. J. Am. Chem. Soc. 1986, 108, 7995-8001.
4. Burley, S. K.; Petsko, G. A. Adv. Protein Chem. 1988, 39, 125-189.
5. Hunter, C. A.; Singh, J.; Thornton, J. M. J. Mol. Biol. 1991, 218, 837-846.
6. Serrano, L.; Bycroft, M.; Fersht, A. R. J. Mol. Biol. 1991, 218, 465-475.
7. McGaughey, G. B.; Gagnes, M.; Rappe, A. K. J. Biol. Chem. 1998, 273, 15458-15463.
8. Cox, E. G.; Cruickshank, D. W. J.; Smith, J. A. S. Proc. R. Soc. London, Ser. A 1958, 247, 1-21.
9. (b) William, D. E. Acta Crystallogr. 1974, A30, 71-74.
10. (c) Hall, D.; Williams, D. E. Acta Crystallogr. 1975, A31, 56-58.
11. (a) Janda, K. C.; Hemminger, J. C.; Winn, J. S.; Novick, S. E.; Harris, S. J.; Klemperer, W. J. Chem. Phys. 1975, 63, 1419-1421.
12. (b) Steed, J. M.; Dixon, T. A.; Klemperer, W. J. Chem. Phys. 1979, 70, 4940-4946.
13. (c) Henson, B. F.; Hartland, G. V.; Venturo, V. A.; Felker, P. M. J. Chem. Phys. 1992, 97, 2189.
14. (d) Ferguson, S. B.; Sanford, E. M.; Seward, E. M.; Diederich, F. J. Am. Chem. Soc. 1991, 113, 5410-5419.
15. (e) Paliwal, S.; Geib, S.; Wilcox, C. S. J. Am. Chem. Soc. 1994, 116, 4497-4498.
16. Hobza, P.; Selzle, H. L.; Schlag E. W. J. Am. Chem. Soc. 1994, 116, 3500-3506.
17. Laatikainen, R.; Ratilainen, J.; Sebastian, R.; Santa, H. J. Am. Chem. Soc. 1995, 117, 11006-11010.
18. Tsuzuki, S.; Uchimaru, T.; Mikami, M.; Tanabe, K. Chem. Phys. Lett. 1996, 206-210.
19. Jaffe, R. L.; Smith, G. D. J. Chem. Phys. 1996, 105, 2780-2788.
20. Chipot, C.; Jaffe, R.; Maiggret, B.; Pearlman, D. A.; Kollman, P. A. J. Am. Chem. Soc. 1996, 118, 11217-11224.
21. Hobza, P.; Selzle, H. L.; Schlag, E. W. J. Phys. Chem. 1996, 100, 18790-18794.
22. Sun, S.; E. R. Bernstein, E. R. J. Phys. Chem. 1996, 100, 13348-13366.
23. Sinnokrot, M. O.; Valeev, E.; Sherrill, C. D. J. Am. Chem. Soc. 2002, 124, 10887-10893.
24. (a) Bhattacharyya, R.; Samanta, U.; Chakrabarti, P. Protein Eng. 2002, 15, 91-100.
25. (b) Thomas, A.; Meurisse, R.; Brasseur, R. Proteins: Struct., Funct., Genet., 2002, 48, 635-644.
26. (c) Thomas, A.; Meurisse, R.; Charloteaux, B.; Brasseur, R. Proteins: Struct., Funct., Genet. 2002, 48, 628-634.
27. (d) Tóth, G.; Watts, C. R.; Murphy, R. F.; Lovas, S. Proteins: Struct., Funct., Genet. 2001, 43, 373-381.
28. (e) Mitchell, J. B. O.; Laskowski, R. A.; Thornton, J. M. Proteins: Struct., Funct. Genet. 1997, 29, 370-380.
29. Chelli, R.; Gervasio, F. L.; Procacci, P.; Schettino, V. J. Am. Chem. Soc. 2002, 124, 6133-6143.
30. Butterfield, S. M.; Patel, P. R.; Waters, M. L. J. Am. Chem. Soc. 2002, 124, 9751-9755.
31. (a) Tatko, C. D.; Waters, M. L. J. Am. Chem. Soc. 2002, 124, 9372-9373.
32. (b) Walters. M. L. Curr. Opin Chem. Biol. 2002, 6, 736-741.
33. Schindelin, H.; Jiang, W.; Inouye, M.; Heinemann. U. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 5119-5123.
34. (a) Das, C.; Shankaramma, S. C.; Balaram, P. Chem.-Eur. J. 2001, 7, 840-847.
35. (b) Aravinda, S.; Shamala, N.; Rajkishore, R.; Gopi, H. N.; Balaram, P. Angew. Chem., Int. Ed. 2002, 41, 3863-3865.
36. Gervasio, F. L.; Chelli, R.; Procacci, P.; Schettino, V. Proteins: Struct., Funct., Genet. 2002, 48, 117-125.7
37. Venkatraman, J.; Shankaramma, S. C.; Balaram, P. Chem. Rev. 2001, 101, 3131-3152.
38. Kaul, R.; Balaram, P. Bioorg. Med. Chem. 1999, 7, 105-117.
39. Prasad, B. V. V.; Balaram, P. CRC Crit. Rev. Biochem. 1984, 16, 307-347.
40. Karle, I. L.; Balaram, P. Biochemistry 1990, 29, 6747-6756.
41. Toniolo, C.; Benedetti, E. Trends Biochem. Sci. 1991, 16, 350-353.
42. Balaram, P. Curr. Opin. Struct. Biol. 1992, 2, 845-851.
43. (a) Sheldrick, G. M. SHELXS 97. Program for Automatic Solution of Crystal Structures; University of Göttingen: Göttingen, Germany, 1997.
44. (b) Sheldrick, G. M. SHELXL 97, Program for crystal structure refinement; University of Göttingen: Göttingen, Germany, 1997.
45. Nordman, C. E.; Nakatsu, K. J. Am. Chem. Soc. 1963, 85, 353-354.
46. Egert, E.; Sheldrick, G. M. Acta Crystallogr. 1985, A41, 262-268.
47. Karle, J. Acta Crystallogr. 1968, B24, 182-186.
48. Vijayalakshmi, S.; Rao, R. B.; Karle, I. L.; Balaram, P. Biopolymers 2000, 53, 84-98.
49. Sheldrick, G. M.; Schneider, T. R. Direct Methods for Macromolecules. Methods in Macromolecular Crystallography; Turk, D., Johnson, L., Eds.; IOS Press: Amsterdam. 2001; pp 72-81.
50. Datta, S.; Shamala, N.; Banerjee, A.; Balaram, P. J. Pept. Res. 1997, 49, 604-611.
51. Baker, E. N.; Hubbard, R. E. Prog. Biophys. Mol. Biol. 1984, 44, 97-179.
52. Chakrabarti, P.; Pal, D. Prog. Biophys. Mol. Biol. 2001, 76, 1-102.
53. (a) Karle, I. L. Acta Crystallogr. 1992, B48, 341-356.
54. (b) Karle, I. L. Biopolymers 1996, 40, 157-180.
55. (c) Karle, I. L. Acc. Chem. Res. 1999, 32, 693-701.
56. (a) Brown, N. M. D.; Swinton, F. L. J. Chem. Soc., Chem. Commun. 1974, 770.
57. (b) Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525-5534.
58. (c) Hunter, C. A.; Lawson, K. R.; Perkins, J.; Urch, C. J. J. Chem. Soc., Perkin Trans. 2 2001, 651-669.
59. Shetty, A. S.; Zhang, J.; Moore, J. S. J. Am. Chem. Soc. 1996, 118, 1019-1027.
60. (a) Gazit, E. FASEB J. 2002, 16, 77-83.
61. (b) Gazit, E. Curr. Med. Chem. 2002, 9, 1667-1675.
62. Birkedal, H.; Schwarzenbach, D.; Pattison, P. Chem. Commun. 2002, 2812-2813.
63. IUPAC-IUB Commission on Biochemical Nomenclature. Biochemistry 1970, 9, 3471-3479.
64. Koradi, R.; Billeter, M.; Wuthrich, K. J. Mol. Graphics 1996, 14, 51-55.