Computational study of phosphatase activity in soluble epoxide hydrolase: High efficiency through a water bridge mediated proton shuttle

Journal of the American Chemical Society

Volumn 127, Issue 32, 2005, Pages 11226-11227

  De Vivo, Marco ^a   Ensing, Bernd ^a   Klein, Michael L ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE HYDROLASE; MAGNESIUM; PHOSPHATASE; PROTON; WATER;

AMINO TERMINAL SEQUENCE; ARTICLE; CATALYSIS; CRYSTAL STRUCTURE; DETOXIFICATION; ENZYME ACTIVITY; FATTY ACID METABOLISM; HYDROLYSIS; MICHAELIS CONSTANT; PHOSPHORYLATION; PROTON TRANSPORT;

ANIMALS; CATALYSIS; COMPUTATIONAL BIOLOGY; COMPUTER SIMULATION; EPOXIDE HYDROLASES; MODELS, MOLECULAR; PHOSPHORIC MONOESTER HYDROLASES; PROTONS; WATER;

EID: 23844483422     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja053049j     Document Type: Article

References (22)

1. (a) Cronin, A.; Mowbray, S.; Durk, H.; Homburg, S.; Fleming, I.; Fisslthaler, B.; Oesch, F.; Arand, M. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 1552.
2. (b) Newman, J. W.; Morisseau, C.; Harris, T. R.; Hammock, B. D. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 1558.
3. Hammock, B. D.; Storms, D. H.; Grant, D. F. Epoxide Hydrolyses, Comprehensive Toxicology, Guengerich, F. P., Ed.: Pergamon: Oxford. 1997; Vol. 3, pp 283-305.
4. (a) Zheng, J.; Plopper, C. G.; Lakritz, J.; Storms, D. H.; Hammock, B. D. Am. J. Respir. Cell. Mol. Biol. 2001, 25, 434.
5. (b) Node, K.; Huo, Y.; Ruan, X.; Yang, B.; Spiecker, M.; Ley, K.; Zeldin, D. C.; Laio, J. K. Science 1999, 285, 1276.
6. (c) Moghaddan, M. F.; Grant, D. F.; Cheek, J. M.; Greene, J. F.; Williamson, K. C.; Hammock, B. D. Nat. Med. 1997, 3, 652.
7. (a) Morais, M. C.; Zhang, W.; Baker, A. S.; Zhang, G.; Dunaway-Mariano, D.; Allen, K. N. Biochemistry 2000, 39, 10385.
8. (b) Gomez, G. A.; Morisseau, C.; Hammock, B. D.; Christianson, D. Biochemistry 2004, 43, 4716.
9. (a) Carloni, P.; Rothlisberger, U.; Parrinello, M. Acc. Chem. Res. 2002, 35, 455.
10. (b) Laio, A.: VandeVondele, J.; Rothlisberger, U. J. Chem. Phys. 2002, 116, 6941.
11. (c) Ciccotti, G.; Ferrario, M.; Hynes, J. T.; Kapral, R. Chem. Phys. 1989, 129, 241.
12. Cornell, W. D.; Cieplak, P.; Bayly, C. I.; Gould, I. R.; Merz, K. M.; Ferguson, D. M.; Spellmeyer, D. C.; Fox, T.; Caldwell, J. W.; Kollman, P. A. J. Am. Chem. Soc. 1995, 117, 5179.
13. 2+ cation plus its six coordinated ligands, namely, the side chains of Asp9 and Asp 185, the backbone of Asp11, two/three water molecules and the phosphate group of the substrate. Figure 1 shows the QM atoms highlighted.
14. -1 reported for the erythro-PHO hydrolysis in ref 1b.
15. (a) Cavalli, A.; De Vivo, M.; Recanatini, M. Chem. Commun. 2003, 1308.
16. (b) Bernardi, F.; Bottoni, A.; De Vivo, M.; Garavelli, M.; Keserii, G.; Náray-Szabó, G. Chem. Phys. Lett. 2002, 362, 1.
17. (a) Lahiri, D. S.; Zhang, G.; Dunaway-Mariano, D.; Allen, N. K. Science 2003, 299, 2067.
18. (b) Allen, N. K.; Dunaway-Mariano, D. Trends Biochem. Sci. 2004, 29, 495.
19. (c) Tremblay, L. W.; Zhang, G.; Dai, J.; Dunaway-Mariano, D.; Allen, N. K. J. Am. Chem. Soc. 2005, 117, 5179.
20. Florian, J.; Warshel, A. J. Phys. Chem. B 1998, 102, 719.
21. (a) Schlichting, I.; Reinstein, J. Nat. Struct. Biol. 1999, 6, 721.
22. (b) Schlichting, I.; Reinstein, J. Biochemistry 1997, 36, 9290.