Mechanistic study of the oxidative N-dealkylation reactions of bis(μ-oxo)dicopper complexes

Journal of the American Chemical Society

Volumn 118, Issue 46, 1996, Pages 11575-11586

  Mahapatra, Samiran ^a   Halfen, Jason A ^a   Tolman, William B ^a  

^a University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER COMPLEX;

ARTICLE; DEALKYLATION; REACTION ANALYSIS; SPECTROPHOTOMETRY; THERMODYNAMICS;

EID: 0029862758     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja962304k     Document Type: Article

References (69)

1. (a) Fox, S.; Karlin, K. D. In Active Oxygen in Biochemistry; Valentine, J. S., Foote, C. S., Greenberg, A., Liebman, J. F., Eds.; Blackie Academic & Professional, Chapman & Hall: Glasgow, Scotland, 1995; pp 188-231.
2. (b) Karlin, K. D.; Tyeklár, Z.; Zuberbühler, A. D. In Bioinorganic Catalysis: Reedijk, J., Ed.; Marcel Dekker, Inc.: New York, 1993; pp 261-315.
3. (c) Kitajima, N.; Moro-oka, Y. Chem. Rev. 1994, 94, 737.
4. (a) Klinman, J. P. Chem. Rev., in press,
5. (b) Stewart, L. C.; Klinman, J. P. Annu. Rev. Biochem. 1988, 57, 551-592.
6. (a) Semrau, J. D.; Zolandz, D.; Lindstrom, M. E.; Chan, S. I. J. Inorg. Biochem. 1995, 58, 235-244.
7. (b) Nguyen, H.-H. T.; Shiemke, A. K.; Jacobs, S. J.; Hales, B. J.; Lindstrom, M. E.; Chan, S. I. J. Biol. Chem. 1994, 269, 14995-15005.
8. (c) Chan, S. I.; Nguyen, H.-H. T.; Shiemke, A. K.; Lidstrom, M. E. In Bioinorganic Chemistry of Copper, Karlin, K. D., Tyeklár, Z., Eds.; Chapman & Hall: New York, 1993; pp 184-195.
9. (a) Merkler, D. J.; Kulathila, R.; Francisco. W. A.; Ash, D. E.; Bell, J. FEBS Lett. 1995, 366, 165-169.
10. (b) Eipper, B. A.; Quon, A. S. W.; Mains, R. E.; Boswell, J. S.; Blackburn, N. J. Biochemistry 1995, 34, 2857-2865.
11. (c) Kulathila, R.; Consalvo, A. P.; Fitzpatrick, P. F.; Freeman, J. C.; Snyder, L. M.; Villafranca, J. J.; Merkler, D. J. Arch. Biochem. Biophys. 1994, 311, 191-195.
12. (d) Merkler, D. J.; Kulathila, R.; Young, S. D.; Freeman, J.; Villafranca, J. J. In Bioinorganic Chemistry of Copper, Karlin, K. D., Tyeklár, Z., Eds.; Chapman & Hall: New York, 1993; pp 196-209.
13. Solomon, E. I.; Baldwin, M. J.; Lowery, M. D. Chem. Rev. 1992, 92, 521-542.
14. Thompson, J. S. In Biological & Inorganic Copper Chemistry; Karlin, K. D., Zubieta, J., Eds.; Adenine Press: New York, 1986; Vol. 2, pp 1-10.
15. (a) Itoh, S.; Kondo, T.; Komatsu, M.; Ohshiro, Y.; Li, C.; Kanehisa, N.; Kai, Y.; Fukuzumi, S. J. Am. Chem. Soc. 1995, 117, 4714-4715.
16. (b) Réglier, M.; Amadéi, E.; Alilou, E. H.; Eydoux, F.; Pierrol, M.; Waegell, B. In Bioinorganic Chemistry of Copper, Karlin, K. D., Tyeklár, Z., Eds.; Chapman & Hall: New York, 1993; pp 348-362.
17. (c) Alilou, E. H.; Amadéi, E.; Giorgi, M.; Pierrot, M.; Réglier, M. J. Chem. Soc., Chem. Commun. 1993, 549-557.
18. Capdevielle, P.; Maumy, M. Tetrahedron Lett. 1991, 32, 3831-3834.
19. (a) Sanyal, I.; Mahroof-Tahir, M.; Nasir, M. S.; Ghosh, P.; Cohen, B. I.; Gultneh, Y.; Cruse, R. W.; Farooq, A.; Karlin, K. D.; Liu, S.; Zubieta, J. Inorg. Chem. 1992, 31, 4322-4332.
20. (b) Sayre, L. M.; Tang, W.; Reddy, K. V.; Nadkarni, D. In Bioinorganic Chemistry of Copper, Karlin, K. D., Tyeklár, Z., Eds.; Chapman & Hall: New York, 1993; pp 236-248.
21. (c) Reddy, K. V.; Jin, S.-J.; Arora, P. K.; Sfeir, D. S.; Maloney, S. C. F.; Urbach, F. L.; Sayre, L. M. J. Am. Chem. Soc. 1990, 112, 2332-2340.
22. (a) Mahapatra, S.; Halfen, J. A.; Wilkinson, E. C.; Pan, G.; Cramer, C. J.; Que, L., Jr.; Tolman, W. B. J. Am. Chem. Soc. 1995, 117, 8865-8866.
23. (b) Halfen, J. A.; Mahapatra, S.; Wilkinson, E. C.; Kaderli, S.; Young, V. G., Jr.; Que, L., Jr.; Zuberbühler, A. D.; Tolman, W. B. Science 1996, 271, 1397-1400.
24. Wimalasena, K.; May, S. W. J. Am. Chem. Soc. 1987, 109, 4036-4046.
25. Katopodis, A. G.; May, S. W. Biochemistry 1990, 29, 4541-4548.
26. Mahapatra, S.; Halfen, J. A.; Wilkinson, E. C.; Que, L., Jr.; Tolman, W. B. J. Am. Chem. Soc. 1994, 116, 9785-9786.
27. Mahapatra. S.; Halfen, J. A., Wilkinson, E. C.; Pan, G.; Wang, X.; Young, V. G., Jr.; Cramer, C. J.; Que, L., Jr.; Tolman, W. B. J. Am. Chem. Soc. 1996, 118, 11555.
28. Cytochrome P450: Structure, Mechanism, and Biochemistry, 2nd ed.; Ortiz de Montellano, P. R., Ed.; Plenum Press: New York, 1995.
29. (a) Que, L., Jr.; True, A. E. Prog. Inorg. Chem. 1990, 38, 97-200.
30. (b) Kurtz, D. M., Jr. Chem. Rev. 1990, 90, 585-606.
31. Baldwin, M. J.; Stemmler, T. L.; Riggs-Gelasco, P. J.; Kirk, M. L.; Penner-Hahn, J. E.; Pecoraro, V. L. J. Am. Chem. Soc. 1994, 116, 11349-11356.
32. (a) Scott, M. J.; Zhang, H. H.; Lee, S. C.; Hedman, B.; Hodgson, K. O.; Holm, R. H. J. Am. Chem. Soc. 1995, 117, 568-569.
33. (b) Fox, S.; Nanthakumar, A.; Wikström, M.; Karlin, K. D.; Blackburn, N. J. J. Am. Chem. Soc. 1996, 118, 24-34.
34. Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165-195.
35. Johnson, C. D. The Hammett Equation; Cambridge University Press: Cambridge, U.K., 1973.
36. Tian, G.; Berry, J. A.; Klinman, J. P. Biochemistry 1994, 33, 226-234.
37. Kitajima, N.; Koda, T.; Iwata, Y.; Moro-oka, Y. J. Am. Chem. Soc. 1990, 112, 8833-8839.
38. Kim, J.; Dong, Y.; Larka, E.; Que, L., Jr. Inorg. Chem. 1996, 35, 2369-2372.
39. Bell, R. P. Adv. Phys. Org. Chem. 1966, 4, 1-29.
40. Ortiz de Montellano, P. R. In ref 15, pp 245-303.
41. Groves, J. T.; Han, Y.-Z. In ref 15, pp 3-48.
42. Newcomb, M.; LeTadic-Biadatti, M. H.; Chestney, D. L.; Roberts, E. S.; Hollenberg, P. F. J. Am. Chem. Soc. 1995, 117, 12085-12091.
43. 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 & Professional: Glasgow, 1995; Vol. 3, pp 84-187.
44. See, for example: Dennocenzo, J. P.; Karki, S. B.; Jones, J. P. J. Am. Chem. Soc. 1993, 115, 7111-7116.
45. Mahapatra, S.; Halfen, J. A.; Houser, R. P.; Young, V. G., Jr.; Tolman, W. B. To be submitted.
46. Russell, G. A. In Free Radicals; Kochi, J. K., Ed.; John Wiley & Sons: New York, 1973; Vol. I, pp 275-331.
47. Vaz, A. D. N.; Coon, M. J. Biochemistry 1994, 33, 6442-6449.
48. Inchley, P.; Lindsay Smith, J. R.; Lower, R. J. New J. Chem. 1989, 13, 669-676.
49. (a) Cook, G. K.; Mayer, J. M. J. Am. Chem. Soc. 1994, 116, 1855-1868.
50. (b) Gardner, K. A.; Mayer, J. M. Science 1995, 269, 1849-1851.
51. Melander, L.; Saunders, W. H., Jr. Reaction Rates of Isotopic Molecules; Wiley-Interscience: New York, 1980.
52. Kwart, H. Acc. Chem. Res. 1982, 15, 408-415.
53. Reinaud, O. M.; Theopold, K. H. J. Am. Chem. Soc. 1994, 116, 6979-6980.
54. (a) Hjelmeland, L. M.; Aronow, L.; Trudell, J. R. Biochem. Biophys. Res. Commun. 1977, 76, 541-549.
55. (b) Groves, J. T.; McClusky, G. A.; White, R. E.; Coon, M. J. Biochem. Biophys. Res. Commun. 1978, 81, 154-160.
56. Glickman, M. H.; Wiseman, J. S.; Klinman, J. P. J. Am. Chem. Soc. 1994, 116, 793-794.
57. (a) Nesheim, J. C.; Lipscomb, J. D. J. Inorg. Biochem. 1995, 59, 369.
58. (b) Nesheim, J. C.; Lipscomb, J. D. Biochemistry 1996, 35, 10240-10247.
59. Large KIEs calculated for hydrogen atom abstractions by atomic oxygen have been related to those for metalloenzyme hydroxylations: Pudzianowski, A. T.; Loew, G. H. J. Phys. Chem. 1983, 87, 1081-1085.
60. Johnson, B. J.; Park, D.-H.; Kim, K.; Plapp, B. V.; Klinman, J. P. Biochemistry 1993, 32, 5503-5507.
61. (a) Lipscomb, J. D. Annu. Rev. Microbiol. 1994, 48, 371-399.
62. (b) Feig, A. L.; Lippard, S. J. Chem. Rev. 1994, 94, 759-805.
63. (c) Shteinman, A. A. FEBS Lett. 1995, 362, 5-9.
64. (d) Que, L., Jr.; Dong, Y. Acc. Chem. Res. 1996, 29, 190-196.
65. Marchanda, R.; Brudvig, G. W.; Crabtree, R. H. Coord. Chem. Rev. 1995, 144, 1-38.
66. (a) Stubbe, J. A. Annu. Rev. Biochem. 1989, 58, 257-285.
67. (b) Metalloenzymes Involving Amino Acid Residue and Related Radicals; Sigel, H., Sigel, A., Eds.; Marcel Dekker: New York, 1994; Vol. 30.
68. Furness, B. S.; Hannaford, A. J.; Smith, P. W. G.; Tatchell, A. R. Vogel's Textbook of Practical Organic Chemistry; Longman Scientific & Technical: Essex, U.K., 1989; p 561.
69. Skoog, D. A. Principles of Instrumental Analysis, 3rd ed.; Saunders College Publishing: New York, 1984; pp 5-22.