Mechanistic studies of the isomerization of peroxynitrite to nitrate catalyzed by distal histidine metmyoglobin mutants

Journal of the American Chemical Society

Volumn 126, Issue 22, 2004, Pages 6945-6955

  Herold, Susanna ^a   Kalinga, Shivashankar ^a   Matsui, Toshitaka ^b   Watanabe, Yoshihito ^c  

^a LABORATORY OF INORGANIC CHEMISTRY   (Switzerland)

^b TOHOKU UNIVERSITY   (Japan)

^c NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; ISOMERIZATION; ISOMERS; NITRATION; PH EFFECTS;

OXIDIZING AGENT; TYROSINE;

NITRATES;

CARBON DIOXIDE; FERRIC ION; HEME; HEMOPROTEIN; HISTIDINE; HISTIDINE METMYOGLOBIN; METMYOGLOBIN; NITRATE; PEROXYNITRITE; TYROSINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DIFFUSION; ISOMERIZATION; NITRATION; OXIDATION; PH; REACTION ANALYSIS; WHALE;

ANIMALS; CATALYSIS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; GLOBINS; HEME; HISTIDINE; HYDROGEN-ION CONCENTRATION; ISOMERISM; KINETICS; METMYOGLOBIN; MUTATION; NITRATES; NITROGEN; PEROXYNITROUS ACID; TYROSINE; WHALES;

EID: 3042771981     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0493300     Document Type: Article

References (49)

1. 2-Tyr, 3-nitrotyrosine.
2. Beckman, J. S.; Beckman, T. W.; Chen, J.; Marshall, P. A.; Freeman, B. A. Proc. Natl. Acad. Sci. U.S.A. 1990, 87, 1620-1624.
3. Lymar, S. V.; Hurst, J. K. J. Am. Chem. Soc. 1995, 117, 8867-8868.
4. Denicola, A.; Freeman, B. A.; Trujillo, M.; Radi, R. Arch. Biochem. Biophys. 1996, 333, 49-58.
5. Meli, R.; Nauser, T.; Koppenol, W. H. Helv. Chim. Acta 1999, 82, 722-725.
6. Floris, R.; Piersma, S. R.; Yang, G.; Jones, P.; Wever, R. Eur. J. Biochem. 1993, 215, 767-775.
7. Sampson, M. B.; Ye, Y.-Z.; Rosen, H.; Beckman, J. S. Arch. Biochem. Biophys. 1998, 356, 207-213.
8. Zou, M.-H.; Daiber, A.; Peterson, J. A.; Shoun, H.; Ullrich, V. Arch. Biochem. Biophys. 2000, 376, 149-155.
9. Daiber, A.; Herold, S.; Schöneich, C.; Namgaladze, D.; Peterson, J. A.; Ullrich, V. Eur. J. Biochem. 2000, 267, 6729-6739.
10. Exner, M.; Herold, S. Chem. Res. Toxicol. 2000, 13, 287-293.
11. Sharpe, M. A.; Cooper, C. E. J. Biol. Chem. 1998, 273, 30961-30972.
12. Pearce, L. L.; Pitt, B. R.; Peterson, J. J. Biol. Chem. 1999, 274, 35763-35767.
13. Herold, S.; Shivashankar, K. Biochemistry 2003, 42, 14036-14046.
14. Jensen, M. P.; Riley, D. P. Inorg. Chem. 2002, 41, 4788-4797.
15. Herold, S.; Matsui, T.; Watanabe, Y. J. Am. Chem. Soc. 2001, 123, 4085-4086.
16. Yang, H.-J.; Matsui, T.; Ozaki, S.; Kato, S.; Ueno, T.; Phillips, G. N., Jr.; Fukuzumi, S.; Watanabe, Y. Biochemistry 2003, 42, 10174-10181.
17. Brancaccio, A.; Cutruzzola, F.; Travaglini-Allocatelli, C.; Brunori, M.; Smerdon, S. J.; Wilkinson, A. J.; Dou, Y.; Keenan, D.; Ikeda-Saito, M.; Brantley, R. E., Jr.; Olson, J. S. J. Biol. Chem. 1994, 269, 13843-13853.
18. Herold, S.; Shivashankar, K.; Mehl, M. Biochemistry 2002, 41, 13460-13472.
19. Koppenol, W. H.; Kissner, R.; Beckman, J. S. Methods Enzymol. 1996, 269, 296-302.
20. Bohle, D. S.; Glassbrenner, P. A.; Hansert, B. Methods Enzymol. 1996, 269, 302-311.
21. Harned, H. S.; Bonner, F. T. J. Am. Chem. Soc. 1945, 67, 1026-1031.
22. Matsui, T.; Ozaki, S.; Watanabe, Y. J. Am. Chem. Soc. 1999, 121, 9952-9957.
23. Ozaki, S.; Hara, I.; Matsui, T.; Watanabe, Y. Biochemistry 2001, 40, 1044-1052.
24. Antonini, E.; Brunori, M. Hemoglobin and Myoglobin in Their Reactions with Ligands; North-Holland: Amsterdam, 1971.
25. Herold, S. Arch. Biochem. Biophys. 1999, 372, 393-398.
26. Koppenol, W. H. In Metals in Biology; Siegel, H., Ed.; Marcel Dekker: New York, 1999; Vol. 36, pp 597-619.
27. Since the reaction is strongly pH dependent (see below), the small differences observed in the second-order rate constants may be attributed to experimental errors in the preparation of solutions with an exact final pH value of 7.5 (see Experimental Procedures).
28. Herold, S. FEBS Lett. 1999, 443, 81-84.
29. Herold, S.; Exner, M.; Nauser, T. Biochemistry 2001, 40, 3385-3395.
30. Groves, J. T. Third International Conference on Peroxynitrite and Reactive Nitrogen Species in Biology and Medicine; Pacific Grove, CA, 2001.
31. Bonini, M. G.; Radi, R.; Ferrer-Sueta, G.; Ferreira, A. M. D. C.; Augusto, O. J. Biol. Chem. 1999, 274, 10802-10806.
32. Goldstein, S.; Czapski, G.; Lind, J.; Merényi, G. Chem. Res. Toxicol. 2001, 14, 1273-1276.
33. Hodges, G. R.; Ingold, K. U. J. Am. Chem. Soc. 1999, 121, 10695-10701.
34. Meli, R.; Nauser, T.; Latal, P.; Koppenol, W. H. J. Biol. Inorg. Chem. 2002, 7, 31-36.
35. Boccini, F.; Domazou, A.; Herold, S. J. Phys. Chem. A 2004, submitted.
36. Koppenol, W. H.; Moreno, J. J.; Pryor, W. A.; Ischiropoulos, H.; Beckman, J. S. Chem. Res. Toxicol. 1992, 5, 834-842.
37. Kissner, R.; Koppenol, W. H. J. Am. Chem. Soc. 2002, 124, 234-239.
38. Bourassa, J. L.; Ives, E. P.; Marqueling, A. L.; Shimanovich, R.; Groves, J. T. J. Am. Chem. Soc. 2001, 123, 5142-5143.
39. Tew, D.; Ortiz de Montellano, P. R. J. Biol. Chem. 1988, 263, 17880-17886.
40. Wilks, A.; Ortiz de Montellano, P. J. Biol. Chem. 1992, 267, 8827-8833.
41. Butler, J.; Land, E. J.; Prütz, W. A.; Swallow, A. J. Biochim. Biophys. Acta 1982, 705, 150-162.
42. Lardinois, O. M.; de Montellano, P. R. O. J. Biol. Chem. 2003, 278, 36214-36226.
43. Lymar, S. V.; Hurst, J. K. Chem. Res. Toxicol. 1996, 9, 845-850.
44. Da Settimo, A. Ann. Chim. (Rome) 1962, 52, 17-24.
45. De Fazi, R.; Berti, G.; Da Settimo, A. Gazz. Chim. Ital. 1959, 89, 2238-2257.
46. Brucker, E. A.; Olson, J. S.; Phillips, G. N., Jr.; Dou, Y.; Ikeda-Saito, M. J. Biol. Chem. 1996, 271, 25419-25422.
47. Smith, R. D. Thesis, Rice University, Houston, TX, 1999.
48. Matsui, T.; Ozaki, S.; Liong, E.; Phillips, G. N., Jr.; Watanabe, Y. J. Biol. Chem. 1999, 274, 2838-2844.
49. Maurus, R.; Bogumil, R.; Luo, Y.; Tang, H.; Smith, M.; Mauk, A.; Brayer, G. J. Biol. Chem. 1994, 269, 12606-12610.