Proton-directed redox control of O-O bond activation by heme hydroperoxidase models

Journal of the American Chemical Society

Volumn 129, Issue 16, 2007, Pages 5069-5075

  Soper, Jake D ^a   Kryatov, Sergey V ^b   Rybak Akimova, Elena V ^b   Nocera, Daniel G ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

^b TUFTS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROLYSIS; HYDROPEROXIDASE ENZYMES; METALLOPORPHYRIN COMPLEXES;

CHEMICAL BONDS; COORDINATION REACTIONS; ENZYMES; ESTERS; PORPHYRINS; REDOX REACTIONS;

PROTONS;

ACID; HANGMAN METALLOPORPHYRIN; HEME HYDROPEROXIDASE; IRON COMPLEX; METALLOPORPHYRIN; OXYGEN; PEROXIDASE; PEROXYACID; PORPHYRIN DERIVATIVE; PROTON; TETRAMESITYLPORPHYRIN; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL STRUCTURE; DISSOCIATION; ELECTRON; ENZYME ACTIVITY; LOW TEMPERATURE; OXIDATION REDUCTION REACTION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

HEME; IRON; MODELS, MOLECULAR; OXIDATION-REDUCTION; OXIDOREDUCTASES; OXYGEN; PEROXIDES; PROTONS;

EID: 34247484862     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0683032     Document Type: Article

References (53)

1. Suslick, K. S. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, 2000; Vol. 4, pp 41-63.
2. Cytochrome P-450 Structure, Mechanism and Biochemistry; Ortiz de Montellano, P. R., Ed.; Plenum Press: New York, 1986.
3. Poulos, T. L.; Fenna, R. E. In Metal Ions in Biological Systems; Sigel, H., Sigel, A., Eds.; Dekker: New York, 1994; Vol. 30, pp 25-75.
4. Rodriguez-Lopez, J. N.; Lowe, D. J.; Hernandez-Ruiz, J.; Hiner, A. N. P.; Garcia-Canovas, F.; Thorneley, R. N. F. J. Am. Chem. Soc. 2001, 123, 11838-11847.
5. Meunier, B. In Biomimetic Oxidations Catalyzed by Transition Metal Complexes; Meunier, B., Ed.; Imperial College: London, 2000; pp 171-214.
6. Sono, M.; Roach, M. P.; Coulter, E. D.; Dawson, J. H. Chem. Rev. 1996, 96, 2841-2887.
7. Ortiz de Montellano, P. R. Cytochrome P450: Structure Mechanism, and Biochemistry, 2nd ed.; Plenum: New York, 1995.
8. Sono, M.; Roach, M. P.; Coulter, E. D.; Dawson, J. H. Chem. Rev. 1996, 96, 2841-2887.
9. Dunford, H. B. Heme Peroxidases; Wiley: New York, 1999.
10. Watanabe, Y. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, 2000; Vol. 4, pp 97-117.
11. Newcomb, M.; Zhang, R., Chandrasena, R. E. P.; Halgrimson, J. A.; Horner, J. H.; Makris, T. M.; Sligar, S. G. J. Am. Chem. Soc. 2006, 128, 4580-4581.
12. Sivaraja, M.; Goodin, D. B.; Smith, M.; Hoffman, B. M. Science 1989, 245, 738-740.
13. Veitch, N. C.; Smith, A. T. Advances in Inorganic Chemistry; Academic Press: New York, 2001; Vol. 51, pp 107-162.
14. Newcomb, M.; Chandrasena, R. E. P. Biochem. Biophys. Res. Commun. 2005, 338, 394-403.
15. Davydov, R.; Chemerisov, S.; Werst, D. E.; Rajh, T.; Matsui, T.; Ikeda-Saito, M.; Hoffman, B. M. J. Am. Chem. Soc. 2004, 126, 15960-15961.
16. Hiner, A. N. P.; Raven, E. L.; Thorneley, R. N. F.; Garcia-Canovas, F.; Rodriguez-Lopez, J. N. J. Inorg. Biochem. 2002, 91, 27-34.
17. Ozaki, S.-I.; Roach, M. P.; Matsui, T.; Watanabe, Y. Acc. Chem. Res. 2001, 34, 818-825.
18. Poulos, T. L.; Kraut, J. J. Biol. Chem. 1980, 255, 8199-8205.
19. Matsui, T.; Ozaki, S-I.; Liong, E.; Phillips, G. N.; Watanabe, Y. J. Biol. Chem. 1999, 274, 2838-2844.
20. Derat, E.; Shaik, S. J. Phys. Chem. B 2006, 110, 10526-10533.
21. Poulos, T. L. In Advances in Inorganic Biochemistry; Eichhorn, G. L., Marzilli, L. G., Eds.; Elsevier: New York, 1988; Vol. 7, pp 1-36.
22. Dawson, J. H. Science 1988, 240, 433-439.
23. Heering, H. A.; Indiani, C.; Regelsberger, G.; Jakopitsch, C.; Obinger, C.; Smulevich, G. Biochemistry 2002, 41, 9237-9247.
24. Fita, I.; Rossmann, M. G. J. Mol. Biol. 1985, 185, 21-37.
25. Green, M. T.; Dawson, J. H.; Gray, H. B. Science 2004, 304, 1653-1656.
26. Green, M. T. J. Am. Chem. Soc. 2006, 128, 1902-1906.
27. Behan, R. K.; Green, M. T. J. Biol. Inorg. Chem. 2006, 100, 448-459.
28. Groves, J. T.; Watanabe, Y. J. Am. Chem. Soc. 1988, 110, 8443-8452.
29. Yamaguchi, K.; Watanabe, Y.; Morishima, I. J. Am. Chem. Soc. 1993, 115, 4058-4065.
30. Traylor, T. G.; Ciccone, J. P. J. Am. Chem. Soc. 1989, 111, 8413-8420.
31. Nam, W.; Lim, M. H.; Oh, S.-Y. Inorg. Chem. 2000, 39, 5572-5575.
32. Watanabe, Y.; Ueno, T. Bull. Chem. Soc. Jpn. 2003, 76, 1309-1322.
33. Yeh, C.-Y.; Chang, C. J.; Nocera, D. G. J. Am. Chem. Soc. 2001, 123, 1513-1514.
34. Chang, C. J.; Yeh, C.-Y.; Nocera, D. G. J. Org. Chem. 2002, 67, 1403-1406.
35. Liu, S.-Y.; Nocera, D. G. J. Am. Chem. Soc. 2005, 127, 5278-5279.
36. Liu, S.-Y.; Soper, J. D.; Yang, J. Y.; Rybak-Akimova, E. V.; Nocera, D. G. Inorg. Chem. 2006, 45, 7572-7574.
37. Chang, C. J.; Chng, L. L.; Nocera, D. G. J. Am. Chem. Soc. 2003, 125, 1866-1876.
38. Chng, L. L.; Chang, C. J.; Nocera, D. G. Org. Lett. 2003, 5, 2421-2424.
39. Bruice, T. C. Acc. Chem. Res. 1991, 24, 243-249.
40. Lee, W. A.; Yuan, L.-C.; Bruice, T. C. J. Am. Chem. Soc. 1988, 110, 4277-4283.
41. IIICl.
42. Groves, J. T.; Haushalter, R. C.; Nakamura, M.; Nemo, T. E.; Evans, B. J. J. Am. Chem. Soc. 1981, 103, 2884-2886.
43. Groves, J. T.; Han, Y. In Cytochrome P-450 Structure, Mechanism and Biochemistry; Ortiz de Montellano, P. R., Ed.; Plenum Press: New York, 1986; pp 3-48.
44. Cheng, R.; Latos-Grazynski, L.; Balch, A. L. Inorg. Chem. 1982, 21, 2412-2418.
45. Calderwood, T. S.; Bruice, T. C. Inorg. Chem. 1985, 25, 3722-3724.
46. Dempsey, J. L.; Esswein, A. J.; Manke, D. R.; Rosenthal, J.; Soper, J. D.; Nocera, D. G. Inorg. Chem. 2005, 44, 6879-6892.
47. Eisenberg, R.; Nocera, D. G. Inorg. Chem. 2005, 44, 6799-6801.
48. Chang, C. J.; Chang, M. C. Y.; Damrauer, N. H.; Nocera, D. G. Biophys. Biochim. Acta 2004, 1655, 13-28.
49. Reece, S. Y.; Hodgkiss, J. M.; Stubbe, J.; Nocera, D. G. Philos. Trans. R. Soc. London, Ser. B 2006, 361, 1351-1364.
50. Lewis, N. S.; Nocera, D. G. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 15729-15735.
51. Nocera, D. G. Dædalus 2006, 135, 112-115.
52. Kadish, K. M; Smith, K. M.; Guilard, R. The Porphyrin Handbook; Academic Press: San Diego, CA, 2000; and references therein.
53. Silbert, L. S.; Siegel, E.; Swern, D. J. Org. Chem. 1962, 27, 1336-1342.