Computational and experimental studies of (2,2)-Bis(indol-1-yl- methyl)acetate suggest the importance of the hydrophobic effect in aromatic stacking interactions

Journal of the American Chemical Society

Volumn 121, Issue 8, 1999, Pages 1717-1725

  Pang, Yuan Ping ^a,b,c   Miller, Jennifer L ^d   Kollman, Peter A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b MAYO CLINIC   (United States)

^c MAYO CLINIC   (United States)

^d NONE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,2 BIS(INDOL 1 YLMETHYL)ACETATE; ACETIC ACID; AROMATIC AMINO ACID; UNCLASSIFIED DRUG; WATER;

ARTICLE; CALCULATION; HYDROPHOBICITY; NUCLEAR MAGNETIC RESONANCE; PROTEIN CONFORMATION; PROTEIN FOLDING; PROTEIN STABILITY; SYNTHESIS;

EID: 0033518870     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9828410     Document Type: Article

References (42)

1. Burley, S. K.; Petsko, G. A. Adv. Protein Chem. 1988, 39, 125.
2. Saenger, W. Principles of Nucleic Acid Structure; Springer-Verlag: New York, 1984.
3. Muller, N. Acc. Chem. Res. 1990, 23, 23.
4. Ts'o, P. O. P. In Basic Principles in Nucleic Acid Chemistry; Ts'o, P. O. P., Ed.; Academic Press: New York, 1974; Vol. I.
5. Crothers, D. M.; Ratner, D. I. Biochemistry 1968, 7, 1823.
6. Ts'o, P. O. P.; Kondo, N. S.; Robins, R. K.; Broom, A. D. J. Am. Chem. Soc. 1969, 91, 5625.
7. Tazawa, I.; Koike, T.; Inoue, Y. Eur. J. Biochem. 1980, 109, 33.
8. Friedman, R. A.; Honig, B. Biophys. J. 1995, 69, 1528-1535.
9. Newcomb, L. F.; Gellman, S. H. J. Am. Chem. Soc. 1994, 116, 4993-4994.
10. Newcomb, L. F.; Haque, T. S.; Gellman, S. H. J. Am. Chem. Soc. 1995, 117, 6509-6519.
11. Gellman, S. H.; Haque, T. S.; Newcomb, L. F. Biophys. J. 1996, 71, 3523-3525.
12. Browne, D. T.; Eisinger, J.; Leonard, N. J. J. Am. Chem. Soc. 1968, 90, 7302-7323.
13. Frank, J. K.; Paul, I. C. J. Am. Chem. Soc. 1973, 95, 2324-2332.
14. Leonard, N. J.; Ito, K. J. Am. Chem. Soc. 1973, 95, 4010-4016.
15. Leonard, N. J. Acc. Chem. Res. 1979, 12, 423.
16. Constant, J. F.; Laugaa, P.; Roques, B. P.; Lhomme, J. Biochemistry 1988, 27, 3997-4003.
17. Mutai, K.; Gruber, B. A.; Leonard, N. J. J. Am. Chem. Soc. 1975, 97, 4095-4104.
18. Voet, D. J. Am. Chem. Soc. 1980, 102, 2071-2074.
19. Ishida, T.; Shibata, M.; Fujii, K.; Inoue, M. Biochemistry 1983, 22, 3571-3581.
20. Friedman, R. A.; Honig, B. Biophys. J. 1996, 71, 3525-3526.
21. Hunter, C. A.; Sanders, K. M. J. Am. Chem. Soc. 1990, 112, 5525-5534.
22. Kollman, P. Chem. Rev. 1993, 93, 2395-2417.
23. Pearlman, D. A.; Case, D. A.; Caldwell, J. W.; Ross, W. S.; Cheatham III, T. E.; Debolt, S.; Ferguson, D.; Seibel, G.; Kollman, P. A. Comput. Phys. Commun. 1995, 91, 1-41.
24. Sun, Y. C.; Veenstra, D. L.; Kollman, P. A. Protein Eng. 1996, 9, 273-281.
25. Tobias, D. J.; Brooks, C. L. J. Chem. Phys. 1988, 89, 5115-5127.
26. Jorgensen, W. L.; Chandreskhar, J.; Madura, J. D.; Impey, R. W.; Klein, M. L. J. Chem. Phys. 1982, 79, 926-935.
27. Silverstein, R. M.; Bassler, G. C.; Morill, T. C. Spectroscopic Identification of Organic Compounds, 5th ed.; Wiley: New York, 1991; p 196.
28. Cornell, W. D.; Cieplak, P.; Bayly, C. I.; Gould, I. R.; Merz, K. M., Jr.; Ferguson, D. M.; Spellmeyer, D. C.; Fox, T.; Caldwell, J. W.; Kollman, P. A. J. Am. Chem. Soc. 1995, 117, 5179-5197.
29. Chipot, C.; Jaffe, R.; Maigret, B.; Pearlman, D. A.; Kollman, P. A. J. Am. Chem. Soc. 1996, 118, 11217-11224.
30. Linse, P. J. Am. Chem. Soc. 1992, 114, 4366.
31. Hobza, P.; Selzle, H. L.; Schlag, E. W. J. Am. Chem. Soc. 1994, 116, 3500-3506.
32. Doebel, K. J.; Wasley, J. W. F. J. Med. Chem. 1972, 15, 1081-1082.
33. Pouchert, C. J.; Belmke, J. The Aldrich library of 13C and 1H FT-NMR spectra; Aldrich Chemical; Milwaukee, WI, 1992.
34. Gaussian 92 and 94; Gaussian, Inc.: Pittsburgh, PA 1992.
35. Bugg, C. E.; Thomas, J. M.; Sundaralingam, M.; Rao, S. T. Biopolymers 1971, 10, 175-219.
36. Janda, K. C.; Hemminger, J. C.; Winn, J. S.; Novick, S. E.; Harris, S. J.; Klemperer, W. J. Chem. Phys. 1975, 63, 1419.
37. Cox, E. G.; Cruikshank, D. W. J.; Smith, J. A. C. Proc. R. Soc. London 1958, 4247, 1.
38. Paliwal, S.; Geib, S.; Wilcox, C. S. J. Am. Chem. Soc. 1994, 116, 4497-4498.
39. Ryckaert, J. P.; Ciccotti, G.; Berendsen, H. J. C. J. Comput. Phys. 1977, 23, 327-341.
40. Berendsen, H. J. C.; Postma, J. P. M.; van Gunsteren, W. F.; Di Nola, A.; Haak, J. R. J. Chem. Phys. 1984, 81, 3684-3690.
41. Cieplak, P.; Cornell, W. D.; Bayly, C.; Kollman, P. A. J. Comput. Chem. 1995, 16, 1357-1377.
42. Pearlman, D. A.; Kollman, P. A. J. Chem. Phys. 1991, 94, 4532-4545.