A DFT study on the formation of a phosphohistidine intermediate in prostatic acid phosphatase

Journal of the American Chemical Society

Volumn 130, Issue 30, 2008, Pages 9708-9716

  Sharma, Satyan ^a   Rauk, Arvi ^b   Juffer, André H ^a  

^a UNIVERSITY OF OULU   (Finland)

^b UNIVERSITY OF CALGARY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACID PHOSPHATASE (ACPASE); ACTIVE SITES; AMERICAN CHEMICAL SOCIETY (ACS); BINDING POCKETS; DEPHOSPHORYLATION; DFT STUDY; HISTIDINE (HIS); NUCLEOPHILIC ATTACKS; PHOSPHATE GROUPS; PHOSPHO-TYROSINE; PROTON DONORS; PROTONATED; QUANTUM CHEMISTRY CALCULATIONS; QUANTUM MODELING; REACTION CATALYZED; TRANSITION STATE (TS); TWO STEP PROCESSES; WATER MOLECULES;

AMINO ACIDS; CATALYSTS; FOOD ADDITIVES; PROTEINS; PROTON TRANSFER; PROTONS; QUANTUM CHEMISTRY;

ENZYMES;

ACID PHOSPHATASE PROSTATE ISOENZYME; ARGININE DERIVATIVE; ASPARTIC ACID; HISTIDINE DERIVATIVE; PROTON;

ARTICLE; CALCULATION; DENSITY FUNCTIONAL THEORY; DEPHOSPHORYLATION; ENZYME ACTIVE SITE; ENZYME MECHANISM; ENZYME SUBSTRATE; ENZYME SYNTHESIS; MOLECULAR MODEL; PROTEIN MOTIF; PROTON TRANSPORT; QUANTUM CHEMISTRY;

BINDING SITES; COMPUTER SIMULATION; GUANIDINES; HISTIDINE; IMIDAZOLES; MODELS, MOLECULAR; PHOSPHORIC ACID ESTERS; PHOSPHORYLATION; PROTEIN TYROSINE PHOSPHATASES; QUANTUM THEORY; WATER;

EID: 48249094980     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja710047a     Document Type: Article

References (43)

1. Horton, H. R.; Moran, L. A.; Scrtmgeour, K. G.; Perry, M. D.; Rawn, J. D. Principles of biochemistry; Pearson Prentice Hall: New York, 2006.
2. Martin, B. L.; Graves, D. J. J. Biol. Chem. 1986, 261, 14545-14550.
3. Kolmodin, K.; Aqvist, J. FEBS Lett. 2001, 498, 208-213.
4. Gutman, E. B.; Sproul, E. E.; Gutman, A. B. Am. J. Cancer 1936, 28, 485-495.
5. Lin, M. F.; DaVolio, J.; Garcia-Arenas, R. Cancer Res. 1992, 52, 4600-4607.
6. Lin, M. F.; Lee, M. S.; Zhou, X. W.; Andressen, J. C.; Meng, T. C.; Johansson, S. L.; West, W. W.; Taylor, R. J.; Anderson, J. R.; Lin, F. F. J. Urol. 2001, 166, 1943-1950.
7. Lin, M. F.; Clinton, G. M. Mol. Cell. Biol. 1988, 8, 5477-5485.
8. Meng, T. C.; Lin, M. F. J. Biol. Chem. 1998, 273, 22096-22104.
9. Sharma, S.; Pirila, P.; Kaija, P. H.; Vihko, P.; Juffer, A. H. Proteins 2005, 58, 295-308.
10. Zhang, Z. Y. Crit. Rev. Biochem. Mol. Biol. 1998, 33, 1-52.
11. Zhang, Z.; Harms, E.; Van Etten, R. L. J. Biol. Chem. 1994, 269, 25947-25950.
12. Ostanin, K.; Saeed, A.; Van Etten, R. L. J. Biol. Chem. 1994, 269, 8971-8978.
13. Van Etten, R. L.; Davidson, R.; Stevis, P. E.; MacArthur, H.; Moore, D. L. J. Biol. Chem. 1991, 266, 2313-2319.
14. Van Etten, R. L. Ann. N. Y. Acad. Sci. 1982, 390, 27-51.
15. Ostanin, K.; Harms, E. H.; Stevis, P. E.; Kuciel, R.; Zhou, M. M.; Van Etten, R. L. J. Biol. Chem. 1992, 267, 22830-22836.
16. Okar, D. A.; Live, D. H.; Devany, M. H.; Lange, A. J. Biochemistry 2000, 39, 9754-9762.
17. Kerovuo, J.; Rouvinen, J.; Hatzack, F. Biochem. J. 2000, 352, 623-628.
18. Porvari, K. S.; Herrala, A. M.; Kurkela, R. M.; Taavitsainen, P. A.; Lindqvist, Y.; G.; Schneider, G.; Vihko, P. T. J. Biol. Chem. 1994, 269, 22642-22646.
19. Zhang, X. Q.; Lee, M.-S.; Zelivianski, S.; Lin, M. F. J. Biol. Chem. 2001, 276, 2544-2550.
20. Ortlund, E.; LaCount, M. W.; Lebioda, L. Biochemistry 2003, 42, 383-389.
21. Frisch, M. J.; et al. Gaussian 98, revision A.11; Gaussian, Inc.: Pittsburgh, PA, 1998.
22. Frisch, M. J.; et al. Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
23. Humbel, S.; Sieber, S.; Morokuma, K. J. Chem. Phy. 1996, 105, 1959-1967.
24. Svensson, M.; Humbel, S.; Froese, R. D. J.; Matsubara, T.; Sieber, S.; Morokuma, K. J. Phys. Chem. 1996, 100, 19357-19363.
25. Froese, R. D. J.; Morokuma, K. In Encyclopedia of Computational Chemistry; Schleyer, P. v. R., Ed.; Wiley: New York, 1998; pp 1245-1247.
26. Cheng, Y.; Zhang, Y.; McCammon, J. A. J. Am. Chem. Soc. 2005, 127, 1553-1562.
27. Alberts, I. L.; Wang, Y.; Schlick, T. J. Am. Chem. Soc. 2007, 129, 11100-11110.
28. Berendsen, H. J. C.; van der Spoel, D.; van Drunen, R. Comput. Phys. Commun. 1995, 91, 43-56.
29. Lindahl, E.; Hess, B.; van der Spoel, D. J. Mol. Mod. 2001, 7, 306-317.
30. Berman, H. M.; Westbrook, J.; Feng, Z.; Gilliland, G.; Bhat, T. N.; Weissig, H.; Shindyalov, I. N.; Bourne, P. E. Nucleic Acids Res. 2000, 28, 235-242.
31. Miertus, S.; Tomasi, J. Chem. Phys. 1982, 65, 239-245.
32. Barone, V.; Cossi, M. J. Phys. Chem. A 1998, 102, 1995-2001.
33. Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Comput. Chem. 2003, 24, 669-681.
34. Asthagiri, D.; Dillet, V.; Liu, T.; Noodleman, L.; van Etten, R. L.; Bashford, D. J. Am. Chem. Soc. 2002, 124, 10225-10235.
35. De Vivo, M.; Ensing, B.; Klein, M. L. J. Am. Chem. Soc. 2005, 127, 11226-11227.
36. Allen, K. N.; Dunaway-Mariano, D. Trends Biochem. Sci. 2004, 29, 495-503.
37. Lee, D. C.; Cottrill, M. A.; Forsberg, C. W.; Jia, Z. J. Biol. Chem. 2003, 278, 31412-31418.
38. Lim, D.; Golovan, S.; Forsberg, C. W.; Jia, Z. Nat. Struct. Biol. 2000, 7, 108-113.
39. Lahiri, S. D.; Zhang, G.; Dunaway-Mariano, D.; Allen, K. N. Science 2003, 299, 2067-2071.
40. Wang, Y.; Liu, L.; Wei, Z.; Cheng, Z.; Lin, Y.; Gong, W. J. Biol. Chem. 2006, 281, 39642-39648.
41. Resat, H.; Straatsma, T. P.; Dixon, D. A.; Miller, J. H. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 6033-6038.
42. Fauman, E. B.; Yuvaniyama, C.; Schubert, H. L.; Stuckey, J. A.; Saper, M. A. J. Biol. Chem. 1996, 271, 18780-18788.
43. Kamerun, S. C. L.; Wilkie, J. Org. Biomol. Chem. 2007, 5, 2098-2108.