On the mechanism of acetylcholinesterase action: The electrostatically induced acceleration of the catalytic acylation step

Journal of the American Chemical Society

Volumn 119, Issue 35, 1997, Pages 8159-8165

  Wlodek, Stanislaw T ^a   Antosiewicz, Jan ^b   Briggs, James M ^c  

^a UNIVERSITY OF HOUSTON   (United States)

^b UNIVERSITY OF WARSAW   (Poland)

^c UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLCHOLINESTERASE;

ACYLATION; ARTICLE; CHEMICAL MODIFICATION; ENZYME ACTIVE SITE; ENZYME ACTIVITY; ENZYME KINETICS; MUTANT; QUANTUM CHEMISTRY; TORPEDO CALIFORNICA;

EID: 0030755235     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja970395v     Document Type: Article

References (35)

1. Nolte, H. J.; Rosenberry, T. L.; Neumann, E. Biochemistry 1980, 19, 3705-3711.
2. Hassinoff, B. B. Biochim. Biophys. Acta 1982, 704, 52-58.
3. Bazelyansky, M.; Robey, E.; Kirsch, J. F. Biochemistry 1986, 25, 125-130.
4. Sussman, J. L.; Harel, M.; Frolow, F.; Oefner, C.; Goldman, A.; Toker, L.; Silman, I. Science 1991, 253, 872-879.
5. Stroud, R. M. Sci. Am. 1974, 213, 74-88.
6. Blow, D. M. Acc. Chem. Res. 1976, 9, 145-152.
7. Kraut, J. Annu. Rev. Biochem. 1977, 46, 331-358.
8. Ordentlich, A.; Barak, D.; Kronman, C.; Flashner, Y.; Leitner, M.; Segall, Y.; Ariel, N.; Cohen, S.; Belan, B.; Shafferman, A. J. Biol. Chem. 1993, 268, 17083-17095.
9. Selwood, T.; States, S. R. Feasterand, M. J.; Pryor, A. N.; Quinn, D. J. Am. Chem. Soc. 1993, 115, 10477-10482.
10. Harel, M.; Quinn, D. M.; Nair, H. K.; Silman, I.; Sussman, J. L. J. Am. Chem. Soc. 1996, 118, 2340-2346.
11. Henderson, R. J. Mol. Biol. 1970, 54, 341-354.
12. Marquart, M.; Walter, J.; Deisenhofer, J.; Bode, W.; Huber, R. Acta Crystallogr., Sect. B 1983, 39, 480-490.
13. Robertus, J. D.; Kraut, J.; Alden, R. A.; Borktoft, J. J. Biochemistry 1972, 11, 4293-4303.
14. Antosiewicz, J.; McCammon, J. A.; Wlodek, S. T.; Gilson, M. K. Biochemistry 1995, 34, 4211-4219.
15. Radić, Z.; Pickering, N. A.; Vellom, D. C.; Camp, S.; Taylor, P. Biochemistry 1993, 32, 12074-12084.
16. Radić, Z.; Gibney, G.; Kawamoto, S.; MacPhee-Quigley, K.; Bongiorno, C.; Taylor, P. Biochemistry 1992, 31, 9760-9767.
17. Quinn, D. M. 1997, personal communication.
18. Pullman, A. Binding sites of acetylcholine in the aromatic gorge leading to the active site of acetylcholinesterase. In Modelling of Biomolecular Structures and Mechanisms; Pullman, A., Jortner, J., Pullman, B., Eds.; Kluwer Academic Publishers. 1995; pp 11-23.
19. Gibney, G.; Camp, S.; Dionne, M.; MacPhee-Quigley, K.; Taylor, P. Proc. Natl. Acad. Sci. U.S.A. 1990, 87, 7546-7550.
20. March, J. Advanced organic chemistry, reactions, mechanisms, and structure; John Wiley & Sons: New York, 1992.
21. Madura, J. D.; Davis, M. E.; Gilson, M. K.; Wade, R. C.; Luty, B. L.; McCammon, J. A. Rev. Comput. Chem. 1994, 5, 229-267.
22. McCammon, J. A.; Northrup, S. H.; Allison, S. A. J. Phys. Chem. 1986, 90, 3901-3905.
23. Davis, M. E.; Madura, J. D.; Luty, B. A.; McCammon, J. A. Comput. Phys. Commun. 1991, 62, 187-197.
24. Madura, J. D.; Briggs, J. M.; Wade, R. C.; Davis, M. E.; Luty, B. A.; Ilin, A.; Antosiewicz, J.; Gilson, M. K.; Bagheri, B.; Scott, L. R.; McCammon, J. A. Comput. Phys. Commun. 1995, 91, 57-95.
25. Warwicker, J.; Watson, H. C. J. Mol. Biol. 1982, 157, 671-679.
26. Antosiewicz, J.; McCammon, J. A.; Gilson, M. K. J. Mol. Biol. 1994, 238, 415-436.
27. Gilson, M. K. Proteins: Struct. Funct. Gen. 1993, 15, 266-282.
28. 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 B.1; Gaussian, Inc.: Pittsburgh, PA, 1995.
29. Radić, Z. 1997. personal communication.
30. Shafferman, A. A.; Ordentlich, A.; Barak, D.; Kronman, C.; Ber, R.; Bino, T.; Ariel, N.; Osman, R.; Velan, B. EMBO J. 1995, 13, 3448-3455.
31. Wlodek, S. T.; Antosiewicz, J.; McCammon, A.; Gilson, M. K. Binding of cations and protons in the active site of acetylcholinesterase. In Modelling of Biomolecular Structures and Mechanisms; Pullman, A.; Jortner, J., Pullman, B., Eds.; Kluwer Academic Publishers: 1995; pp 25-37.
32. Dive, G.; Dehareng, D.; Peeters, D. J. Quant. Chem. 1996, 58, 85-107.
33. Blow, D. M.; Birktoft, J. J.; Hartley, B. S. Nature 1969, 221, 337-340.
34. Vasilyev, V. V. J. Mol. Str. 1994, 304, 129-141.
35. MSI. InsightII; Molecular Simulations, Inc.: San Diego, CA, 1996.