Ionic hydrogen bonds in bioenergetics. 4. Interaction energies of acetylcholine with aromatic and polar molecules

Journal of the American Chemical Society

Volumn 121, Issue 7, 1999, Pages 1546-1557

  Deakyne, Carol A ^a   Meot Ner, Michael ^b,c  

^a EASTERN ILLINOIS UNIVERSITY   (United States)

^b NATIONAL INSTITUTE OF STANDARDS AND TECHNOLOGY   (United States)

^c UNIVERSITY OF CANTERBURY   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLCHOLINE; AROMATIC COMPOUND; ION;

ARTICLE; BIOENERGY; CONFORMATIONAL TRANSITION; HYDROGEN BOND; MEMBRANE CHANNEL; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; RECEPTOR BINDING;

EID: 0033599359     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja982549s     Document Type: Article

References (68)

1. Sussman, J. L.; Harel, M.; Frolow, F.; Oefner, C.; Goldman, A.; Toker, L.; Silman, I. Science 1991, 253, 871-879.
2. Sussman, J. L.; Silman, I. Curr. Opin. Struct. Biol. 1992, 2, 721-729.
3. Harel, M.; Quinn, D. M.; Nair, H. K.; Silman, I.; Sussman, J. L. J. Am. Chem. Soc. 1996, 118, 2340-2346.
4. Dougherty, D. A.; Stauffer, D. A. Science 1990, 250, 1558-1560.
5. Kumpf, R. A.; Dougherty, D. A. Science 1993, 261, 1708-1710.
6. Dougherty, D. A. Science 1996, 271, 163-168.
7. Meot-Ner (Mautner), M. In Computational Approaches in Supramolecular Chemistry; Wippf, G., Ed.; Kluwer Academic: Dordrecht, 1994; NATO ASI Series C, Vol. 426, pp 31-49.
8. Taylor, R.; Kennard, O. Acc. Chem. Res. 1984, 17, 320-326.
9. Meot-Ner (Mautner), M.; Deakyne, C. A. J. Am. Chem. Soc. 1985, 107, 469-474.
10. Steiner, T.; Saenger, W. J. Am. Chem. Soc. 1992, 114, 10146-10154.
11. Aakeröy, C. B.; Sneddon, K. R. Chem. Soc. Rev. 1993, 22, 397-407.
12. Lee, J. Y.; Lee, S. J.; Choi, H. S.; Cho, S. J.; Kim, K. S.; Ha, T.-K. Chem. Phys. Lett. 1995, 232, 67-71.
13. Viswamitra, M. A.; Radhakrishnan, R.; Bandekar, J.; Desiraju, G. R. J. Am. Chem. Soc. 1993, 115, 4868-4869.
14. Gil, F. P. S. C.; Amorim da Costa, A. M.; Teixeira-Dias, J. J. C. J. Phys. Chem. 1995, 99, 8066-8070.
15. Meot-Ner (Mautner), M. J. Am. Chem. Soc. 1988, 110, 3071-3075.
16. Meot-Ner (Mautner), M. J. Am. Chem. Soc. 1984, 106, 1265-1272.
17. Deakyne, C. A.; Meot-Mer (Mautner), M. J. Am. Chem. Soc. 1985, 107, 474-479.
18. Deakyne, C. A. J. Phys. Chem. 1986, 90, 6625-6632.
19. Deakyne, C. A. Mol. Struct. Energ. 1987, 4, 105-141.
20. Kim, K. S.; Lee, J. Y.; Lee, S. J.; Ha, T.-K.; Kim, D. H. J. Am. Chem. Soc. 1994, 116, 7399-7400.
21. Basch, H.; Stevens, W. J. J. Mol. Struct. (THEOCHEM) 1995, 338, 303-315.
22. Fuxreiter, M.; Warshel, A. J. Am. Chem. Soc. 1998, 120, 183-194.
23. Meot-Ner (Mautner), M.; Sieck, L. W. J. Am. Chem. Soc. 1991, 113, 4448-4460.
24. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B. Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, Revision C.3, NIST, 1995; Gaussian, Inc.: Pittsburgh, PA. Use of this program does not indicate NIST endorsement of this product.
25. Tsuzuki, S.; Uchimaru, T.; Tanabe, K.; Hirano, T. J. Phys. Chem. 1993, 97, 1346-1350.
26. Alemán, C.; Navas, J. J.; Muñoz-Guerra, S. J. Phys. Chem. 1995, 99, 17653-17661.
27. Watanabe, H.; Iwata, S. J. Phys. Chem. 1996, 100, 3377-3386.
28. Meot-Ner (Mautner), M.; Sieck, L. W.; Koretke, K. K.; Deakyne, C. A. J. Am. Chem. Soc. 1997, 119, 10430-10438.
29. Del Bene, J. E. J. Phys. Chem. 1988, 92, 2874-2880.
30. Pudzianowski, A. T. J. Chem. Phys. 1995, 102, 8029-8039.
31. Pullman, A.; Berthier, G.; Savinelli, R. J. Am. Chem. Soc. 1998, 120, 8553-8554.
32. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; John Wiley & Sons: New York. 1986.
33. Grev, R. S.; Janssen, C. L.; Schaefer, H. F., III J. Chem. Phys. 1991, 95, 5128-5132.
34. Meot-Ner (Mautner), M. J. Phys. Chem. 1991, 95, 6580-6585.
35. Hunter, E. P.; Lias, S. G. Proton Affinity Evaluation in NIST Chemistry WebBook, NIST Standard Data Base Number 69; Mallard, W. G., Linstrom, P. J., Eds.; National Institute of Standards and Technology: Gaithersburg, March 1998 (http://webbook.nist.gov).
36. Yamdagni, R.; Kebarle, P. J. Am. Chem. Soc. 1973, 95, 3504-3510.
37. Meot-Ner (Mautner), M.; Hamlet, P.; Hunter, E. P.; Field, F. H. J. Am. Chem. Soc. 1980, 102, 6393-6399.
38. Liquori, A. M.; Damiani, A.; De Coen, J. L. J. Mol. Biol. 1968, 33, 445-450.
39. Culvenor, C. C. J.; Ham, N. S. Chem. Commun. 1966, 537-539.
40. Svinning, T.; Sørum, H. Acta Crystallogr., Sect. B 1975, 31, 1581-1586.
41. Jagner, S.; Jensen, B. Acta Crystallogr., Sect. B 1977, 33, 2757-2762.
42. Datta, N.; Mondal, P.; Pauling, P. Acta Crystallogr., Sect. B 1980, 36, 906-909.
43. Harmon, K. M.; Akin, A. C.; Avci, G. F.; Nowos, L. S.; Tierney, M. B. J. Mol. Struct. 1991, 244, 223-236.
44. Desiraju, G. R. Acc. Chem. Res. 1991, 24, 290-296.
45. Jeffrey, G. A.; Saenger, W. Hydrogen Bonding in Biological Structures; Springer: Berlin, 1991.
46. Meot-Ner (Mautner), M.; Sieck, L. W.; Scheiner, S.; Duan, X. J. Am. Chem. Soc. 1994, 116, 7848-7856.
47. Meot-Ner (Mautner), M.; Scheiner, S. J. Am. Chem. Soc. In press.
48. Herdklotz, J. K.; Sass, R. L. Biochem. Biophys. Res. Commun. 1970, 40, 583-588.
49. Mahajan, V.; Sass, R. L. J. Cryst. Mol. Struct. 1974, 4, 15-21.
50. Mhin, B. J.; Kim, J.; Kim, K. S. Chem. Phys. Lett. 1993, 216, 305-308.
51. Bazelyansky, M.; Robey, C.; Kirsch, J. F. Biochemistry 1986, 25, 125-130.
52. Quinn, D. M. Chem. Rev. 1987, 87, 955-979.
53. Shafferman, A.; Kronman, C.; Flashner, Y.; Leitner, M.; Grosfeld, H.; Ordentlich, A.; Gozes, Y.; Cohen, S.; Ariel, N.; Barak, D.; Harel, M.; Silman, I.; Sussman, J. L.; Velan, B. J. Biol. Chem. 1992, 267, 17640-17648.
54. Radic, Z.; Gibney, G.; Kawamoto, S.; MacPhee-Quigley, K.; Bongiorno, C.; Taylor, P. Biochemistry 1992, 31, 9760-9767.
55. Ordentlich, A.; Barak, D.; Kronman, C.; Flashner, Y.; Leitner, M.; Segall, Y.; Ariel, N.; Cohen, S.; Velan, B.; Shafferman, A. J. Biol. Chem. 1993, 268, 17083-17095.
56. Froede, H. C.; Wilson, I. B. In The Enzymes, 3rd ed.; Boyer, P. D., Ed.; Academic Press: New York, 1971; Vol. 5, pp 87-114.
57. Eastman, J.; Wilson, E. J.; Cerveñansky, C.; Rosenberry, T. L. J. Biol. Chem. 1995, 270, 19694-19701.
58. Harel, M.; Schalk, I.; Ehret-Sabatier, L.; Bouet, F.; Goeldner, M.; Hirth, C.; Axelsen, P. H.; Silman, I.; Sussman, J. L. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 9031-9035.
59. Hosea, N. A.; Radic, Z.; Tsigelny, I.; Berman, H. A.; Quinn, D. M.; Taylor, P. Biochemistry 1996, 35, 10995-11004.
60. Antosiewicz, J.; Wlodek, S. T.; McCammon, J. A. Biopolymers 1996, 39, 85-94.
61. Gentry, M. K.; Doctor, B. P. In Cholinesterases: Structure, Function, Mechanism, Genetics, and Cell Biology; Massoulié, J., Bacou, F., Barnard, E., Chatonnet, A., Doctor, B. P., Quinn, D. M., Eds.; American Chemical Society: Washington, DC, 1991; pp 394-398.
62. Taylor, P.; Lappi, S. Biochemistry 1975, 14, 1989-1997.
63. Adam, G.; Delbruck, M. In Structurai Chemistry in Molecular Biology; Rich, A., Davidson, N., Eds.; Freeman: San Francisco, 1968; pp 198-215.
64. Eigen, M. In Quantum Statistical Mechanics in the Natural Sciences; Mintz, S. L., Widinger, S. M., Eds.; Plenum: New York, 1974; pp 37-61.
65. Pang, Y.-P.; Quiram, P.; Jelacic, T.; Hong, F.; Brimijoin, S. J. Biol. Chem. 1996, 271, 23646-23649.
66. Guo, B. C.; Purnell, J. W.; Castleman, A. W., Jr. Chem. Phys. Lett. 1990, 168, 155-160.
67. Sunner, J.; Nishizawa, K.; Kebarle, P. J. Phys. Chem. 1981, 85, 1814-1820.
68. Schowen, K. B.; Smissman, E. E.; Stephen, W. F., Jr. J. Med. Chem. 1975, 18, 292-300.