Hydrogen tunneling steps in cyclooxygenase-2 catalysis

Journal of the American Chemical Society

Volumn 133, Issue 40, 2011, Pages 15846-15849

  Danish, Husain H ^a   Doncheva, Irina S ^a   Roth, Justine P ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOOXYGENASE 2; DEUTERIUM KINETIC ISOTOPE EFFECT; HEMOPROTEINS; HOMOLYSIS; HYDROGEN ATOM ABSTRACTION; NUCLEAR TUNNELING; PHYSIOLOGICAL LEVELS; TEMPERATURE DEPENDENT; TYROSYL RADICALS;

ABSTRACTING; AMINO ACIDS; BIOCHEMISTRY; CATALYSIS; DEUTERIUM; LINOLEIC ACID; RATE CONSTANTS;

HYDROGEN;

CARBON; CYCLOOXYGENASE 2; DEUTERIUM; DIOXYGENASE; HYDROGEN; LINOLEIC ACID; OXYGEN; PEROXIDASE; TYROSINE;

ARTICLE; CATALYSIS; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME METABOLISM; FATTY ACID OXIDATION; KINETICS; STEADY STATE; STOICHIOMETRY; TEMPERATURE DEPENDENCE;

ANIMALS; CYCLOOXYGENASE 2; HYDROGEN; LINOLEIC ACID; MICE; MODELS, MOLECULAR; OXIDATION-REDUCTION;

EID: 80053465271     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja2059523     Document Type: Article

References (33)

1. Rouzer, C. A.; Marnett, L. J. Chem. Rev. 2003, 103, 2239
2. Smith, W. L.; DeWitt, D. L.; Garavito, R. M. Annu. Rev. Biochem. 2000, 69, 145
3. Halliwell, B.; Gutteridge, J. M. C. Free Radicals in Biology and Medicine, 3 rd Ed.; Oxford University Press: New York, 2005.
4. Marnett, L. J. Annu. Rev. Pharmacol. Toxicol. 2009, 49, 265
5. Menter, D. G.; Schilsky, R. L.; DuBois, R. N. Clin. Cancer Res. 2010, 16, 1384
6. Tsai, A.-L.; Kulmacz, R. J. Arch. Biochem. Biophys. 2010, 493, 103
7. van der Ouderaa, F. J.; Buytenhek, M.; Nugteren, D. H.; Van Dorp, D. A. Biochim. Biophys. Acta 1977, 487, 315
8. Tsai, A.-L.; Hsi, L. C.; Kulmacz, R. J.; Palmer, G.; Smith, W. L. J. Biol. Chem. 1994, 269, 5085
9. Mukherjee, A.; Brinkley, D. W.; Chang, K. M.; Roth, J. P. Biochemistry 2007, 46, 3975
10. Hamberg, M. Arch. Biochem. Biophys. 1998, 349, 376
11. Malkowski, M. G.; Ginell, S. L.; Smith, W. L.; Garavito, R. M. Science 2000, 289, 1933
12. Vecchio, A. J.; Simmons, D. M.; Malkowski, M. G. J. Biol. Chem. 2010, 285, 22152
13. Dong, L.; Vecchio, A. J.; Sharma, N. P.; Jurban, B. J.; Malkowski, M. G.; Smith, W. L. J. Biol. Chem. 2011, 286, 19035
14. Lewis, E.; Johansen, E.; Holman, T. R. J. Am. Chem. Soc. 1999, 121, 1395)
15. Mukherjee, A. Ph.D. Dissertation, Johns Hopkins University, Baltimore, MD, 2009.
16. See the Supporting Information for details.
17. Hsuanyu, Y.; Dunford, H. B. J. Biol. Chem. 1992, 267, 17649
18. Wu, G.; Tsai, A.-L.; Kulmacz, R. J. Biochemistry 2009, 48, 11902
19. Kulmacz, R. J.; van der Donk, W. A.; Tsai, A.-L. Prog. Lipid Res. 2003, 42, 377
20. Yuan, C.; Rieke, C. J.; Rimon, G.; Wingerd, B. A.; Smith, W. L. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 6142
21. Goodwin, D. C.; Rowlinson, S. W.; Marnett, L. J. Biochemistry 2000, 39, 5422
22. Glickman, M. H.; Klinman, J. P. Biochemistry 1995, 34, 14077
23. Hamberg, M.; Samuelsson, B. J. Biol. Chem. 1967, 242, 5336
24. Schneider, C.; Brash, A. R. J. Biol. Chem. 2000, 275, 4743
25. Gupta, A.; Mukherjee, A.; Matsui, K.; Roth, J. P. J. Am. Chem. Soc. 2008, 130, 11274
26. Mukherjee, A.; Angeles-Boza, A. M.; Huff, G. S.; Roth, J. P. J. Am. Chem. Soc. 2011, 133, 227
27. Huff, G. S.; Doncheva, I. D.; Brinkley, D. W.; Angeles-Boza, A. M.; Mukherjee, A.; Cramer, C. J.; Roth, J. P. Biochemistry 2011, 50, 7375
28. Wu, G.; Lü, J.-M.; van der Donk, W. A.; Kulmacz, R. J.; Tsai, A.-L. J. Inorg. Biochem. 2011, 105, 382
29. Nagel, Z, D.; Klinman, J. P. Nat. Chem. Biol. 2009, 5, 543
30. Hammes-Schiffer, S. Acc. Chem. Res. 2006, 39, 93
31. Schwartz, S. D; Schramm, V. L. Nat. Chem. Biol. 2009, 5, 551
32. Johannissen, L. O.; Scrutton, N. S.; Sutcliffe, M. J. Angew. Chem., Int. Ed. 2011, 50, 2129
33. Knapp, M. J.; Seebeck, F. P.; Klinman, J. P. J. Am. Chem. Soc. 2001, 123, 2931