On the role of the conserved aspartate in the hydrolysis of the phosphocysteine intermediate of the low molecular weight tyrosine phosphatase

Journal of the American Chemical Society

Volumn 126, Issue 39, 2004, Pages 12677-12684

  Asthagiri, D ^a,c   Liu, Tiqing ^a,d   Noodleman, Louis ^a   Van Etten, Robert L ^b   Bashford, Donald ^a,e  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b PURDUE UNIVERSITY   (United States)

^c LOS ALAMOS NATIONAL LABORATORY   (United States)

^d MONTANA STATE UNIVERSITY   (United States)

^e Jude Children's Research Hospital   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CATALYSIS; ELECTROSTATICS; HYDROGEN BONDS; HYDROLYSIS; MOLECULAR WEIGHT; ORGANIC COMPOUNDS; OXYGEN; SOLUTIONS; SOLVENTS; WATER;

CONTINUUM ELECTROSTATICS MODEL; DEPHOSPHORYLATION; RATE DETERMINING STEPS; TYROSINE PHOSPHATASES;

ENZYMES;

ANION; ASPARTIC ACID; BASE; CYSTEINE; DEUTERIUM; ORGANOPHOSPHATE; OXYGEN; PHOSPHATASE; PHOSPHOAMINO ACID; PHOSPHOCYSTEINE; PHOSPHORUS ACID DERIVATIVE; SOLVENT; TYROSINE PHOSPHATASE; UNCLASSIFIED DRUG; WATER;

ARTICLE; BINDING AFFINITY; CATALYSIS; CHEMICAL REACTION; DEPHOSPHORYLATION; DEUTERIUM KINETIC ISOTOPE EFFECT; ENERGY BARRIER; ENERGY TRANSFER; ENZYME MECHANISM; HYDROGEN BOND; HYDROLYSIS; MOLECULAR WEIGHT; NUCLEOPHILE; NUCLEOPHILIC ATTACK; PKA; PROTON TRANSPORT; REACTION INTERMEDIATE; SOLVENT ISOTOPE EFFECT; TRANSITION STATE;

ANIMALS; ASPARTIC ACID; CATTLE; CYSTEINE; HYDROLYSIS; KINETICS; MODELS, MOLECULAR; MOLECULAR WEIGHT; PHOSPHORYLATION; PROTEIN-TYROSINE-PHOSPHATASE; QUANTUM THEORY; THERMODYNAMICS;

EID: 4644309817     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja048638o     Document Type: Article

References (60)

1. Fischer, E. H.; Charbonneau, H.; Tonks, N. K. Science 1991, 253, 401-406.
2. Hunter, T. Cell 2000, 100, 113-127.
3. Kikawa, K. D.; Vidale, D. R.; Van Etten, R. L.; Kinch, M. S. J. Biol. Chem. 2002, 277, 39274-39279.
4. Jackson, M. D.; Denu, J. M. Chem. Rev. 2001, 101, 2313-3240
5. Zhang Z.-Y. Crit. Rev. Biochem. Mol. Biol. 1998, 33, 1-52.
6. Zhang Z.-Y.; Van Etten, R. L. J. Biol. Chem. 1991, 266, 1516-1525.
7. Dillet, V.; Van Etten, R. L.; Bashford, D. J. Phys. Chem. B 2000, 104, 11321-11333.
8. Asthagiri, D.; Dillet, V.; Liu, T.; Noodleman, L.; Van Etten, R. L.; Bashford, D. J. Am. Chem. Soc. 2002, 124, 10225-10235.
9. Zhang, Z.-Y.; Van Etten, R. L. Biochemistry 1991, 30, 8954-8959.
10. Denu, J. M.; Lohse, D. L.; Vijayalakshmi, J.; Saper, M. A.; Dixon, M. E. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 2493-2498.
11. Lohse, D. L.; Denu, J. M.; Santoro, N.; Dixon, J. E. Biochemistry 1997, 36, 4568-4575.
12. Zhang, Z.; Harms, E.; Van Etten, R. L. J. Biol. Chem. 1994, 269, 25947-25950.
13. Zhao, Y.; Zhang, Z.-Y. Biochem. 1996, 35, 11797-11804.
14. Bartmess, J. E. Negative ion energetics data. In NIST chemistry webbook; Linstrom, P. J., Mallard, W. G., Eds.; NIST standard reference database number 69; NIST: Gaithersberg, MD, 2001; http://webbook.nist.gov.
15. Zhang, Z.-Y. J. Biol. Chem. 1995, 270, 11190-11204.
16. Zhang, Z.-Y.; Malachowski, W. P.; Van Etten, R. L.; Dixon, J. E. J. Biol. Chem. 1994, 269, 8140-8145.
17. Zhang, Z.-Y.; Wu, L.; Chen, L. Biochem. 1995, 34, 16088-16096.
18. Zhang, Z. Mechanistic, kinetic, and chemical modification studies of low molecular weight protein tyrosine phosphatases. Thesis, Purdue University, 1994.
19. Wang, S.; Stauffacher, C. V.; Van Etten, R. L. Biochemistry 2000, 39, 1234-1242.
20. Wu, L.; Zhang, Z.-Y. Biochem. 1996, 35, 5426-5434.
21. Zhang, M.; Zhou, M.; Van Etten, R. L.; Stauffacher, C. V. Biochemistry 1997, 36, 15-23.
22. MacKerell, A. D., Jr.; Bashford, D.; Bellott, M.; Dunbrack, R. L., Jr.; Evanseck, J. D.; Field, M. J.; Fischer, S.; Gao, J.; Guo, H.; Ha, S.; Joseph-McCarthy, D.; Kuchnir, L.; Kuczera, K.; Lau, F. T. K.; Mattos, C.; Michnick, S.; Ngo, T.; Nguyen, D. T.; Prodhom, B.; Reiher, W. E., III; Roux, B.; Schlenkrich, M.; Smith, J. C.; Store, R.; Straub, J.; Watanabe, M.; Wiókiewicz-Kuczera, J.; Yin, D.; Karplus, M. J. Phys. Chem. B 1998, 102, 3586-3616.
23. Brooks, B. R.; Bruccoleri, R. E.; Olafson, B. D.; States, D. J.; Swaminathan, S.; Karplus, M. J. Comput. Chem. 1983, 4, 187-217.
24. Alhambra, C.; Gao, J. J. Comput. Chem. 2000, 21, 1192-1203.
25. Stewart, J. J. P. J. Comput. Chem. 1989, 10, 209-220.
26. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, Ö.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mannucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Salvador, P.; Dannenberg, J. J.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komáromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98; Gaussian, Inc.: Pittsburgh, PA, 1998.
27. Guerra, C. F.; Snijders, J. G.; te Velde, G.; Baerends, E. J. Theor. Chem. Acc. 1998, 99, 391-403.
28. Te Velde, G.; Bickelhaupt, F. M.; Baerends, E. J.; Fonseca Guerra, C.; Van Gisbergen, S. J. A.; Snijders, J. G.; Ziegler, T. J. Comput. Chem. 2001, 22, 931-967.
29. ADF 2.3, SCM, Theoretical Chemistry, Vrije Universiteit: Amsterdam, The Netherlands; http://www.scm.com.
30. Vosko, S. H.; Wilk, L.; Nusair, M. Can, J. Phys, 1980, 58, 1200-1211.
31. Becke, A. D. Phys. Rev. A 1988, 38, 3098.
32. Perdew, J. P. Phys. Rev. B 1986, 33, 8822-8824.
33. Head, J. D.; Zerner, M. C. Adv. Quant. Chem. 1988, 20, 1-100.
34. Li, J.; Nelson, M. R.; Peng, C. Y.; Bashford, D.; Noodleman, L. J. Phys. Chem. A 1998, 102, 6311-6324.
35. Keese, R. G.; Castleman, A. W., Jr. J. Am. Chem. Soc. 1989, 111, 9015-9018.
36. Wu, Y. D.; Houk, K. N. J. Am. Chem. Soc. 1993, 115, 11997-12002.
37. Ma, B.; Xie, Y.; Shen, M.; Schleyer, P. v. R.; Schaefer, H. F., III. J. Am. Chem. Soc. 1993, 115, 11169-11179.
38. Schulz, P. A.; Mead, R. D.; Jones, P. L.; Lineberger, W. C. J. Chem. Phys. 1982, 77, 1153.
39. Muftakhov, M. V.; Vasil'ev, Y. V.; Mazunov, V. A. Rapid Commun. Mass Spectrom. 1999, 13, 1104-1108.
40. Morris, R. A.; Knighton, W. B.; Viggiano, A. A.; Hoffman, B. C.; Schaefer, H. F., III. J. Chem. Phys. 1997, 106, 3545-3547.
41. Rudnyi, E. B.; Vovk, O. M.; Sidirov, L. N.; Sorokin, I. D.; Alikhanyan, A. S. High Temp. 1986, 24, 56.
42. Richardson, W. H.; Peng, C.-Y.; Bashford, D.; Noodleman, L.; Case, D. A. Int. J. Quantum Chem. 1997, 61, 207-217.
43. Chen, J. L.; Noodleman, L.; Case, D. A.; Bashford, D. J. Phys. Chem. 1994, 98, 11059-11068.
44. Hu, C.-H.; Brinck, T. J. Phys. Chem. A 1999, 103, 5379-5386.
45. Maegley, K. A.; Admiraal, S. J.; Herschlag, D. Proc. Natl. Acad. Sci. 1996, 93, 8160-8166.
46. Evans, B.; Tishmack, P. A.; Pokalsky, C.; Zhang, M.; Van Etten, R. L. Biochemistry 1996, 35, 13609-13617.
47. Zhang, Z.-Y.; Dixon, J. E. Biochemistry 1993, 32, 9340-9345.
48. Denu, J. M.; Dixon, J. E. Proc. Natl. Acad. Sci. 1995, 92, 5910-5914.
49. Mildvan, A. S. Proteins 1997, 29, 401-416.
50. Menger, F. M. Acc. Chem. Res. 1985, 18, 128-134.
51. Menger, F. M. Biochemistry 1992, 31, 5368-5373.
52. Herschlag, D.; Jencks, W. P. J. Am. Chem. Soc. 1989, 111, 7587-7596.
53. Thatcher, G. R. J.; Kluger, R. Adv. Phys. Org. Chem. 1989, 25, 99-265.
54. Admiraal, S. J.; Herschlag, D. J. Am. Chem. Soc. 2000, 122, 2145-2148.
55. Holtz, K. M.; Catrina, I. A.; Hengge, A. C.; Kantrowitz, E. R. Biochemistry 2000, 39, 9451-9458.
56. Valiev, M.; Kawai, R.; Adams, J. A.; Weare, J. H. J. Am. Chem. Soc. 2003, 125, 9926-9927.
57. Díaz, N.; Field, M. J. J. Am. Chem. Soc. 2004, 126, 529-542.
58. Hart, J. C.; Sheppard, D. W.; Hillier, I. H.; Burton, N. A. Chem. Commun. 1999, 79-80.
59. Hutter, M. C.; Helms, V. Protein Sci. 1999, 8, 2728-2733.
60. Hirano, Y.; Hata, M.; Hoshino, T.; Tsuda, M. J. Phys. Chem. B 2002, 106, 5788-5792.