New insights into the mechanisms of O-O bond cleavage of hydrogen peroxide and tert-alkyl hydroperoxides by iron(III) porphyrin complexes

Journal of the American Chemical Society

Volumn 122, Issue 36, 2000, Pages 8677-8684

  Nam, Wonwoo ^a   Han, Hui Jung ^a   Oh, So Young ^a   Lee, Yoon Jung ^a   Choi, Mee Hwa ^a   Han, So Yeop ^a   Kim, Cheal ^b   Woo, Seung Kyun ^c   Shin, Woonsup ^c  

^a Ewha Womans University   (South Korea)

^b Seoul National University of Science and Technology   (South Korea)

^c Sogang University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

FERRIC ION; HYDROGEN PEROXIDE; HYDROPEROXIDE; METAL COMPLEX; PORPHYRIN; TERTIARY ALKYL GROUP;

ARTICLE; CATALYSIS; CHEMICAL BINDING; CHEMICAL REACTION KINETICS; ELECTRIC POTENTIAL; EPOXIDATION; OXIDATION; REACTION ANALYSIS;

EID: 0034644399     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja994403e     Document Type: Article

References (88)

1. (a) Ortiz de Montellano, P. R. Cytochrome P450: Structure, Mechanism, and Biochemistry, 2nd ed.; Plenum Press: New York, 1995.
2. (b) Sono, M.; Roach, M. P.; Coulter, E. D.; Dawson, J. H. Chem. Rev. 1996, 96, 2841-2887.
3. Shimada, H.; Sligar, S. G.; Yeoni, H.; Ishimura, Y. In Oxygenases and Model Systems; Funabiki, T., Ed.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1997; pp 195-221.
4. Erman, J. E.; Hager, L. P.; Sligar, S. G.Adv. Inorg. Biochem. 1994,10, 71-118.
5. (a) Franzen, S.; Roach, M. P.; Chen, Y.-P.; Dyer, R. B.; Woodruff, W. H.; Dawson, J. H. J. Am. Chem. Soc. 1998, 720, 4658-4661.
6. (b) Dawson, J. H. Science 1988, 240, 433-439.
7. (a) Poulos, T. L. J. Biol. Inorg. Chem. 1996,1,356-359.
8. (b) Goodin, D. B. J. Biol. Inorg. Chem. 1996, 1, 360-363.
9. Rietjens, I. M. C. M.; Osman, A. M.; Veeger, C.; Zakharieva, O.; Antony, J.; Grodzicki, M.; Trautwein, A. X. J. Biol. Inorg. Chem. 1996, 1, 372-376.
10. (a) Watanabc, Y. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic: New York, 2000; Vol. 4, Chapter 30, pp 97-117.
11. (b) Ingold, K. U.; MacFaul, P. A. In Biomimetic Oxidations Catalyzed by Transition Metal Complexes; Meunier, B., Ed.; Imperial College Press: London, 2000; pp 45-89.
12. McLain, J. L.; Lee, J.; Groves, J. T. In Biomimetic Oxidations Catalyzed by Transition Metal Complexes; Meunier, B., Ed.; Imperial College Press: London, 2000, pp 91-169.
13. Watanabe, Y. In Oxygenases and Model Systems; Funabiki, T., Ed.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1997; pp 223-282.
14. (e) Traylor, T. G.; Traylor, P. S. In Active Oxygen in Biochemistry; Valentine, J. S., Foote, C. S., Greenberg, A., Liebman, J. F., Eds.; Blackie Academic and Professional, Chapman and Hall: London, 1995; pp 84-187.
15. (f) Montanari, F.; Casella, L. Metalloporphyrins Catalyzed Oxidations; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1994.
16. (g) Meunier, B. Chem. Rev. 1992, 92, 1411-1456.
17. (a) Groves, J. T.; Haushalter, R. C.; Nakamura, M.; Nemo, T. E.; Evans, B. J. J. Am. Chem. Soc. 1981,103, 2884-2886.
18. (b) Groves, J. T.; Watanabe, Y. J. Am. Chem. Soc. 1986,108,7834-7836.
19. Groves, J. T.; Watanabe, Y. J. Am. Chem. Soc. 1988, 110, 8443-8452.
20. (a) Traylor, T. G.; Lee, W. A.; Stynes, D. V. J. Am. Chem. Soc. 1984. 106, 755-764.
21. (b) Lee, W. A.; Bruice, T. C. J. Am. Chem. Soc. 1985. 707, 513-514.
22. Mandon, D.; Weiss, R.; Jayaraj, K.; Gold, A.; Temer, J.; Bill, E.; Trautwein, A. X. Inorg. Chem. 1992, 31, 4404-4409.
23. Fujii, H. Chem. Lett. 1994, 1491-1494.
24. (a) Traylor, T. G.; Kirn, C.; Fann, W.-P.; Perrin, C. L. Tetrahedron 1998,54, 7977-7986.
25. (b) Traylor, T. G.; Kirn, C.; Richards, J. L.; Xu, F.; Perrin, C. L. J. Am. Chem. Soc. 1995,117, 3468-3474.
26. Traylor, T. G.; Tsuchiya, S.; Byun, Y.-S.; Kim, C. J. Am. Chem. Soc. 1993, 115, 2775-2781.
27. Traylor, T. G.; Fann, W.-P.; Bandyopadhyay, D. J. Am. Chem. Soc. 1989, 111, 8009-8010.
28. (e) Traylor, T. G.; Ciccone, J. P. J. Am. Chem. Soc. 1989, 111, 8413-8420.
29. (f) Traylor, T. G.; Xu, F. J. Am. Chem. Soc. 1987, 709, 6201-6202.
30. Traylor, T. G.; Xu, F. J. Am. Chem. Soc. 1990, 772, 178-186.
31. (a) Almarsson, O.; Bruice, T. C. J. Am. Chem. Soc. 1995,117,4533-4544 and references therein.
32. (b) Arasasingham, R, D.; Bruice, T. C. In The Activation of Dioxygen and Homogeneous Catalytic Oxidation; Barton, D. H. R., Martell, A. E., Sawyer, D. T., Eds., Plenum Press: New York, 1993; pp 147-169.
33. Bruice, T. C. Ace. Chem. Res. 1991, 24, 243-249.
34. He, G.-X.; Bruice, T. C. J. Am. Chem. Soc. 1991,113, 2747-2753.
35. (a) Minisci, F.; Fontana, F.; Araneo, S.; Recupero, F.; Banfi, S.; Quici, S. J. Am. Chem. Soc. 1995, 117, 226-232.
36. (b) Arasasingham, R. D.; Comman, C. R.; Balch, A. L. J. Am. Chem. Soc. 1989, 111, 7800-7805.
37. Labeque, R.; Marnett, L. J. J. Am. Chem. Soc. 1989, 111, 6621-6627.
38. Labeque, R.; Mamett, L. J. Biochemistry 1988, 27, 7060-7070.
39. (a) Colclough, N.; Lindsay Smith, J. R. In The Activation of Dioxygen and Homogeneous Catalytic Oxidation; Barton, D. H. R., Martell, A. E., Sawyer, D. T., Eds.; Plenum Press: New York, 1993; pp 171-182.
40. (b) Bell, S. E. J.; Cooke, P. R.; Inchley, P.; Leanord, D. R.; Lindsay Smith, J. R.; Robbins, A. J. Chem. Soc., Perkin Trans. 2 1991, 549-559.
41. (a) Matsui, T.; Ozaki, S.; Watanabe, Y. J. Am. Chem. Soc. 1999, 121, 9952-9957.
42. (b) Adachi, S.; Nagano, S.; Ishimori, K.; Watanabe, Y.; Morishima, L; Egawa, T.; Kitagawa, T.; Makino, R. Biochemistry 1993, 32, 241-252.
43. Allentoff, A. J.; Bolton, J. L.; Wilks, A.; Thompson, J. A.; Ortiz de Montellano, P. R. J. Am. Chem. Soc. 1992,114, 9744-9749.
44. (a) Nam, W.; Choi, H. J.; Han, H. J.; Cho, S. H.; Lee, H. J.; Han, S.-Y. Chem. Commun. 1999, 387-388.
45. (b) Yang, S. J.; Nam, W. tnorg. Chem. 1998, 37, 606-607.
46. Goh, Y. M.; Nam, W. Inorg. Chem. 1999, 38, 914-920.
47. (a) Deeth, R. J.; Dalton, H. J. Biol. Inorg. Chem. 1998, 3, 302-306.
48. (b) Whittington, D. A.; Valentine, A. M; Lippard, S. J. J. Biol. Inorg. Chem. 1998,3, 307-313.
49. Shteinman, A. A. J. Biol. Inorg. Chem. 1998, 3, 325-330.
50. Lipscomb, J. D.; Que, L., J. Biol. Inorg. Chem. 1998, 3, 331-336.
51. (a) Valentine, A. M.; Stahl, S. S.; Lippard, S. J. J. Am. Chem. Soc. 1999,121,3876-3887.
52. (b) Basch, H.; Mogi, K.; Musaev, D. G.; Morokuma, K. J. Am. Chem. Soc. 1999,121, 7249-7256.
53. Que, L., Jr.; Ho, R. Y. N. Chem. Rev. 1996, 96, 2607-2624.
54. Wallar, B. J.; Lipscomb, J. D. Chem. Rev. 1996, 96, 2625-2657.
55. III-OOC(O)R, are significantly affected by the electronic nature of iron porphyrin complexes and solvents: (a) Yamaguchi, K.; Watanabe, Y.; Morishima, I. J. Am. Chem. Soc. 1993, 115, 4058-4065.
56. (b) Higuchi, T.; Shimada, K.; Maruyama, N.; Hirobe, M. J. Am. Chem. Soc. 1993, 115, 7551-7552.
57. (a) MacFaul, P. A.; Wayner, D. D. M.; Ingold, K. U. Ace. Chem. Res. 1998,31, 159-162.
58. (b) MacFaul, P. A.; Ingold, K. U.; Wayner, D. D. M.; Que, L., Jr. J. Am. Chem. Soc. 1997,119,10594-10598.
59. Oldroyd, R. D.; Thomas, J. M.; Maschmeyer, T.; MacFaul, P. A.; Snelgrove, D. W.; Ingold, K. U.; Wayner, D. D. M. Angew. Chem., Int. Ed. Engl. 1996, 55, 2787-2790.
60. Arenas, I. W. C. E.; Ingold, K. U.; Wayner, D. D. M. J. Am. Chem. Soc. 1995, 117, 4710-4711.
61. (a) Lee, K. A.; Nam, W. J. Am. Chem. Soc. 1997, 119, 1916-1922.
62. (b) Nam, W.; Lee, H. J.; Lim, M. H.; Kim, C. J. Am. Chem. Soc. 2000, 722, 6641-6647.
63. Quinn, R.; Nappa, M.; Valentine, J. S. J. Am. Chem. Soc. 1982, IM, 2588-2595.
64. Sheldon, R. A.; Kochi, J. K. Metal-Catalyzed Oxidations of Organic Compounds; Academic Press: New York, 1981.
65. Minisci, F.; Fontana, F.; Araneo, S.; Recupero, F.; Zhao, L. Synlett 1996, 119-125.
66. (a) Kadish, K. M. In Iron Porphyrins, Part II; Lever, A. B. P., Gray, H. B., Eds; Addison-Wesley Publishing Company: London, 1983; pp 161-249.
67. (b) Wijesekera, T.; Matsumoto, A.; Dolphin, D.; Lexa, D. Angew. Chem., Int. Ed. 1990, 29, 1028-1030.
68. Chen, H. L.; Ellis, P. E., Jr.; Wijesekera, T.; Hagan, T. E.; Groh, S. E.; Lyons, J. E.; Ridge, D. P. J. Am. Chem. Soc. 1994, 116, 1086-1089. (d) Grinstaff, M. W.; Hill, M. G.; Labinger, J. A.; Gray, H. B. Science 1994, 264, 1311-1313.
69. (a) Yamaguchi, K.; Watanabe, Y.; Morishima, I. Inorg. Chem. 1992, 31,156-157. (b) Groves, J. T.; Watanabe, Y. Inorg. Chem. 1986,25,4808-4810.
70. Liu, H. I.; Sono, M.; Kadkhodayan, S.; Hager, L. P.; Hedman, B.; Hodgson, K. O.; Dawson, J. H. J. Biol. Chem. 1995, 270, 10544-10550.
71. Choudhury, K.; Sundaramoorthy, M.; Hickman, A.; Yonetani, T.; Woehl, E.; Dunn, M. F.; Poulos, T. L. J. Biol. Chem. 1994, 269, 20239-20249.
72. (a) Suzuki, N.; Higuchi, T.; Urano, Y.; Kikuchi, K.; Uekusa, H.; Ohashi, Y.; Uchida, T.; Kitagawa, T.; Nagano, T. J. Am. Chem. Soc. 1999, 121,11571-11572.
73. (b) Ueno, T.; Kousumi, Y.; Yoshizawa-Kumagaye, K.; Nakajima, K.; Ueyama, N.; Okaraura, T.; Nakamura, A. J. Am. Chem. Soc. 1998, 720, 12264-12273.
74. Ueyama, N.; Nishikawa, N.; Yamada, Y.; Okamura, T.; Nakamura, A. J. Am. Chem. Soc. 1996,118, 12826-12827.
75. III-OOR species and the pathways of the O-O bond cleavage. Some examples showing theoretical approach for explaining the formation of compound I in heme-containing enzymes are as follows: (a) Wirstam, M.; Blomberg, M. R. A.; Siegbahn, P. E. M. J. Am. Chem. Soc. 1999, 727,10178-10185.
76. (b) Harris, D. L.; Loew, G. H. J. Am. Chem. Soc. 1998, 720, 8941-8948.
77. Woon, D. E.; Loew, G. H. J. Phys. Chem. A 1998, 702, 10380-10384.
78. III-OOR species but no't facilitate O-O bond heterolysis.
79. (a) MacFaul, P. A.; Arends, I. W. C. E.; Ingold, K. U.; Wayner, D. D. M. J. Chem. Soc., Perkin Trans. 2 1997, 135-145.
80. (b) Ingold, K. U.; Snelgrove, D. W.; MacFaul, P. A.; Oldroyd, R. D.; Thomas, J. M. Calai. Lett. 1997, 48, 21-24.
81. Snelgrove, D. W.; MacFaul, P. A.; Ingold, K. U.; Wayner, D. D. M. Tetrahedron Lett. 1996, 37, 823-826.
82. (a) Neimann, K.; Neumann, R.; Rabion, A.; Buchanan, R. M.; Fish, R. H. Inorg. Chem. 1999, 38, 3575-3580.
83. (b) Menage, S.; Galey, J.-B.; Dumats, J.; Hussler, G.; Seite, M.; Luneau, I. G.; Chottard, G.; Fontecave, M. J. Am. Chem. Soc. 1998, 720, 13370-13382.
84. Rabion, A.; Chen, S.; Wang, J.; Buchanan, R. M.; Seris, J.-L.; Fish, R. H. J. Am. Chem. Soc. 1995, 117, 12356-12357.
85. Nam, W.; Ho, R.; Valentine, J. S. J. Am. Chem. Soc. 1991, 113, 7052-7054.
86. IV=O intermediates: (a) Lange, S. J.; Miyake, H.; Que, L., Jr. J. Am. Chem. Soc. 1999, 121, 6330-6331.
87. (b) Chen, K.; Que, L., Jr. Chem. Commun. 1999, 1375-1376.
88. Kim, C.; Chen, K.; Kim, J.; Que, L., Jr. J. Am. Chem. Soc. 1997, 119, 5964-5965.