Functional analogues of the dioxygen reduction site in cytochrome oxidase: Mechanistic aspects and possible effects of CuB

Journal of the American Chemical Society

Volumn 124, Issue 40, 2002, Pages 11923-11935

  Boulatov, Roman ^a   Collman, James P ^a   Shiryaeva, Irina M ^a   Sunderland, Christopher J ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME OXIDASE;

BIOMIMETIC MATERIALS; BONDING; ELECTRODES; ENZYMES; OXIDATION; PH;

REDUCTION;

COPPER DERIVATIVE; CYTOCHROME C OXIDASE; HEME DERIVATIVE; HYDROGEN PEROXIDE; OXYGEN; OXYGEN DERIVATIVE;

AQUEOUS SOLUTION; ARTICLE; AUTOOXIDATION; BINDING SITE; CATALYSIS; COMPLEX FORMATION; CONCENTRATION RESPONSE; ENZYME ACTIVE SITE; ENZYME KINETICS; ENZYME STRUCTURE; MOLECULAR MECHANICS; MOLECULAR STABILITY; OXIDATION KINETICS; OXYGEN TRANSPORT; PH; REDUCTION; STEADY STATE; SURFACE CHARGE;

BINDING SITES; CATALYSIS; COPPER; ELECTROCHEMISTRY; ELECTRON TRANSPORT COMPLEX IV; HEME; HYDROGEN PEROXIDE; HYDROGEN-ION CONCENTRATION; KINETICS; MOLECULAR MIMICRY; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; OXYGEN;

EID: 0037048592     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja026179q     Document Type: Article

References (75)

1. Babcock, G. T. Proc. Natl. Acad. Sci. U.S.A. 1999, 96. 12971.
2. Michel, H.; Behr, J.; Harrenga, A.; Kannt, A. Annu. Rev. Biophys. Biomol. Struct. 1998, 27, 329.
3. Pereira, M. M.; Santana, M.; Teixeira, M. Biochim. Biophys. Acta 2001, 1505, 185.
4. Zaslavsky, D.; Gennis, R. B. Biochim. Biophys. Acta 2000, 1458, 164.
5. Ferguson-Miller, S.; Babcock, G. T. Chem. Rev. 1996, 96, 2889.
6. Abramson, J.; Riistama, S.; Larsson, G.; Jasaitis, A.; Svensson-Ek, M.; Laakkonen, L.; Puustinen, A.; Iwata, S.; Wikström, M. Nat. Struct. Biol. 2000, 7, 910.
7. Sono, M.; Roach, M. P.: Coulter, E. D.; Dawson, J. H. Chem. Rev. 1996, 96, 2841.
8. Poulos, T. L. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, CA, 2000; Vol. 4, pp 189-218.
9. Traylor, T. G.; Traylor, P. S. In Active Oxygen in Biochemistry; Valentine, J. S., Foote. C. S., Greenberg, A., Liebman, J. F., Eds.; Chapman and Hall: New York. 1995; Vol. 3, pp 84-187.
10. Loew, G. H.; Harris, D. L. Chem. Rev. 2000, 100, 407.
11. Veitch, N. C.; Smith, A. T. Adv. Inorg. Chem. 2001, 51, 107.
12. de Montellano, P. R. O. Cytochrome P450, 2nd ed.; Plenum: New York, 1995.
13. Nicholls, P.; Fita, I.; Loewen, P. C. Adv. Inorg. Chem. 2001, 51, 51.
14. Yoshikawa, S.; Shinzawa-Itoh, K.; Nakashima, R.; Yaono, R.; Yamashita, E.; Inoue, N.; Yao, M.; Fei, M. J.; Libeu, C. P.; Mizushima. T.; Yamaguchi, H.; Tomizaki, T.; Tsukihara, T. Science 1998, 280, 1723.
15. Morgan, J. E.; Verkhovsky, M. I.; Palmer, G.; Wikström, M. Biochemistry 2001, 40, 6882.
16. Proshlyakov, D. A.; Pressler, M. A.; DeMaso, C.; Leykam, J. F.; DeWitt, D. L.; Babcock, G. T. Science 2000, 290, 1588.
17. Fabian, M.; Wong, W. W.; Gennis, R. B.; Palmer, G. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 13114.
18. Blomberg, M. R. A.; Siegbahn, P. E. M.; Babcock, G. T.; Wikström, M. J. Am. Chem. Soc. 2000, 122, 12848.
19. Calhoun, M. W.; Hill, J. J.; Lemieux, L. J.; Ingledew, W. J.; Alben, J. O.; Gennis, R. B. Biochemistry 1993, 32, 11524.
20. Mogi, T.; Hirano, T.; Nakamura, H.; Anraku, Y.; Orii, Y. FEBS Lett. 1995, 370, 259.
21. Brown, S.; Rumbley, J. N.; Moody, A. J.; Thomas, J. W.; Gennis, R. B.; Rich, P. R. Biochim. Biophys. Acta 1994, 1183, 521.
22. Lemon, D. D.; Calhoun, M. W.; Gennis, R. B.; Woodruff, W. H. Biochemistry 1993, 32, 11953.
23. Collman, J. P.; Boulatov, R.; Sunderland, C. J. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, 2003; Vol. 11, in press.
24. Collman, J. P.; Sunderland, C. J.; Boulatov, R. Inorg. Chem. 2002, 41, 2282.
25. 25b
26. Collman, J. P.; Berg, K.; Sunderland, C. J.; Vance, M. A.; Solomon, E. I. Inorg. Chem. 2002, in press.
27. McCreery, R. L. Electroanal. Chem. 1990, 17, 221.
28. See the Supplementary information for the relevant figures.
29. Shiryaeva, I. M.; Collman, J. P.; Boulatov, R.; Sunderland, C. J. Anal. Chem. 2002, submitted.
30. 30), probably reflecting the additional stabilization of the positive charge by the more σ-basic proximal imidazole.
31. Kaaret, T. W.; Zhang, G.-H.; Bruice, T. C. J. Am. Chem. Soc. 1991, 113, 4652.
32. Su, Y. O.; Kuwana, T.; Chen, S. M. J. Electroanal. Chem. 1990, 288, 177.
33. Zipplies, M. F.; Lee, W. A.; Bruice, T. C. J. Am. Chem. Soc. 1986, 108, 4433.
34. Boulatov, R.; Collman, J. P.; Shiryaeva, I. M.; Sunderland, C. J. Angew. Chem., Int. Ed. 2002, in press.
35. Yoshikawa, S.; Mochizuki, M.; Zhao, X.-J.; Caughey, W. S. J. Biol. Chem. 1995, 270, 4270.
36. He, B.; Sinclair, R.; Copeland, B. R.; Makino, R.; Powers, L. S.; Yanazaki, I. Biochemistry 1996, 35, 2413.
37. See for example chapter 14 in ref 36.
38. Bard, A. J.; Faulkner, L. R. Electrochemical Methods; Wiley: New York, 2001.
39. d).
40. 2.
41. 2/s and solution viscosity as 0.01 s/cm.
42. Hutchison, J. E.; Postlethwaite, T. A.; Chen, C.-h.; Hathcock, K. W.; Ingram, R. S.; Ou, W.; Linton, R. W.; Murray, R. W.; Tyvoll, D. A.; Chng, L. L.; Collman, J. P. Langmuir 1997, 13, 2143.
43. 2.
44. Huie, R. E.; Neta, P. In Reactive Oxygen Species in Biological Systems: An Interdisciplinary Approach; Gilbert, D. L., Colton, C. A., Eds.; Kluwer: New York, 1999; pp 33-63.
45. Jovanovic, S. V.; Steenken, S.; Tosic, M.; Marjanivic, B.; Simic, M. G. J. Am. Chem. Soc. 1994, 116, 4846.
46. Bielski, B. H. J. In Oxy Radicals and Their Scavenger Systems; Cohen, G., Greenwald, R. A., Eds.; Elsevier: New York, 1983; Vol. 1, pp 1-7.
47. Dikalov, S.; Khramtsov, V.; Zimmer, G. Arch. Biochem. Biophys. 1996, 326, 207.
48. Sies, H. Methods Enzymol. 1994, 234, 476.
49. Halliwell, B.; Gutteridge, J. M. C. Methods Enzymol. 1990, 186, 1.
50. Watanabe, Y. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, CA, 2000; Vol. 4, pp 97-117.
51. Weiss, R.; Gold, A.; Trautwein, A. X.; Terner, J. In The Porphyrin Handbook: Kadish. K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, CA, 2000; Vol. 4, pp 65-96.
52. Anson, F. C.; Tsou, Y.-M.; Saveant, J.-M. J. Electroanal. Chem. 1984, 178, 113.
53. Andrieux, C. P.; Saveant, J.-M. In Molecular Design of Electrode Surfaces; Murray, R. W., Ed.; Wiley: New York, 1992; Vol. 22, pp 207-270.
54. Kobayashi, N.; Nishiyama, Y. J. Electroanal. Chem. 1984, 181, 107.
55. Conway, B. E.; Bockris, J. O. M.; Yeager, E.; Khan, S. U. M.; White, R. E. Comprehensive Treatise of Electrochemistry; Plenum: New York, 1983; Vol. 7.
56. The TDS is defined as the first irreversible step after substrate binding.
57. + mass-transport and, as a result, are lower than those observed in buffered solutions of the same acidity. The first ∼50% of the catalytic waves in unbuffered solutions coincide with those measured in buffered electrolytes, as do Tafel plots of these early parts. Thus, a buffer is essential to maintain bulk acidity at the electrode surface, not as a reactant in the catalytic cycle.
58. Shigehara, K.; Anson, F. C. J. Phys. Chem. 1982, 86, 2776.
59. 2 partitioning between the film and electrolyte as 1: the precise value of this coefficient does not affect the mechanistic conclusions.
60. Momenteau, M.; Reed, C. A. Chem. Rev, 1994, 94, 659.
61. 62
62. Cunningham, I. D.; Danks, T. N.: O'Connell, K, T. A.; Scott, P. W. J. Chem. Soc., Perkin Trans. 2 1999, 2133.
63. Shikama, K. Chem. Rev. 1998, 98, 1357.
64. Adachi, S.; Nagano, S.; Ishimori, K.; Watanabe, Y.; Morishima, I.; Egawa, T.; Kitagawa, T. Biochemistry 1993, 32, 241.
65. Collman, J. P.; Sunderland, C. J. Manuscript in preparation.
66. Shi, C.; Anson, F. C. Inorg. Chem. 1990, 29, 4298.
67. Collman, J. P.; Boulatov, R. Angew. Chem., Int. Ed. 2002, in press.
68. Stanbury, D. M.; Haas, O.; Taube, H. Inorg. Chem. 1980, 19, 518.
69. Brantley, R. E.: Smerdon, S. J.; Wilkinson, A. J.; Singleton, E. W.; Olson, J. S. J. Biol. Chem. 1993, 268, 6995.
70. Chance, B.; Sies, H.; Boveris, A. Physiol. Rev. 1979, 59, 527.
71. Gilbert, D. L.; Colton, C. A. Reactive Oxygen Species in Biological Systems: An Interdisciplinary Approach; Kluwer: New York, 1999; Chapters 3 and 7.
72. Collman, J. P.; Berg, K. E.; Sunderland, C. J.; Shiryaeva, I. M. To be reported.
73. Vogel, A. I. Vogel's Textbook of Quantitative Chemical Analysis, 6th ed.; Prentice Hall: Harlow, U.K., 2000.
74. Verkhovsky, M. I.; Morhan, J. E.; Wikstrom, M. Biochemistry 1995, 34, 7483.
75. Rich, P. R.; Moody, A. J. In Bioenergetics; P. Graber, Milazzo, G., Eds.; Birkhauser: Basel, Switzerland, 1997; Vol. 4, pp 418-456.