Hydroxylation of methane by non-heme diiron enzymes: Molecular orbital analysis of C-H bond activation by reactive intermediate Q

Journal of the American Chemical Society

Volumn 124, Issue 49, 2002, Pages 14608-14615

  Baik, Mu Hyun ^a   Gherman, Benjamin F ^a   Friesner, Richard A ^a   Lippard, Stephen J ^b  

^a Och Spine at New York Presbyterian Hospitals   (United States)

^b MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIFERROMAGNETISM; CARBON; ELECTRONIC STRUCTURE; ENZYMES; HYDROGEN; HYDROXYLATION; PROTONS;

ELECTRON TRANSFER PROCESS;

METHANE;

CARBON; HEME; HYDROGEN; METHANE; METHANE MONOOXYGENASE; OXYGENASE;

ARTICLE; ATOM; CHEMICAL STRUCTURE; DERIVATIZATION; ELECTRON TRANSPORT; ELECTRONICS; HYDROGEN BOND; HYDROXYLATION; MAGNETISM; MOLECULAR DYNAMICS; OXIDATION REDUCTION REACTION; PROTON TRANSPORT; QUANTITATIVE ANALYSIS; REACTION ANALYSIS; SOLUBILITY;

ELECTRONS; HYDROXYLATION; IRON; METALLOPROTEINS; METHANE; MODELS, MOLECULAR; OXYGENASES; SOLUBILITY;

EID: 0037065357     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja026794u     Document Type: Article

References (90)

1. Feig, A. L.; Lippard, S. J. Chem. Rev. 1994. 94, 759.
2. Liu, K. E.; Lippard, S. J. Adv., Inorg. Chem. 1995, 42, 263.
3. Wallar, B. J.; Lipscomb. J. D. Chem. Rev. 1996, 96, 2625.
4. Merkx, M.; Kopp, D. A.; Sazinsky, M. H.; Blazyk, J. L.; Muller, J.; Lippard, S. J. Angew. Chem., Int. Ed. 2001, 40, 2782.
5. Rosenzweig, A. C.; Nordlund, P.; Takahara, P. M.; Frederick, C. A.; Lippard, S. J. Chem. Biol. 1995, 2, 409.
6. Rosenzweig, A. C.; Frederick, C. A.; Lippard, S. J.; Nordlund, P. Nature 1993, 366, 537.
7. Whittington, D. A.; Lippard, S. J. J. Am. Chem. Soc. 2001, 123, 827.
8. Elango, N.; Radhakrishnan, R.; Froland, W. A.; Wallar, B. J.; Earhart, C. A.; Lipscomb, J. D.; Ohlendorf, D. H. Protein Sci. 1997, 6, 556-568.
9. Shu, L, J.; Nesheim, J. C,; Kauffmann, K,; Münck, E.; Lipscomb, J. D.; Que. L. Science 1997, 275, 515.
10. Nordlander, E.; Andersson, K. K. J. Biol. Inorg. Chem. 1998, 3, 300.
11. Deeth, R. J.; Dalton, H. J. Biol. Inorg. Chem. 1998, 3, 302.
12. Whittington, D. A.; Valentine, A. M.; Lippard, S. J. J. Biol. Inorg. Chem. 1998, 3, 307.
13. Shteinman, A. A. J. Biol. Inorg. Chem. 1998, 3, 325.
14. Lipscomb, J. D.; Que, L. J. Biol. Inorg. Chem. 1998, 3, 331.
15. (a) Brazeau, B. J.; Lipscomb, J. D. Biochemistry 2000, 39, 13503.
16. (b) Brazeau, B. J.; Austin, R. N.; Tarr, C.; Groves, J. T.; Lipscomb, J. D. J. Am. Chem. Soc. 2001, 123, 11831.
17. (c) Brazeau, B. J.; Wallar, B. J.; Liscomb, J. D. J. Am. Chem. Soc. 2001, 123, 10421.
18. (d) Valentine, A. M.; Stahl, S. S.; Lippard, S. J. J. Am. Chem. Soc. 1999, 121, 3876.
19. (e) Nesheim, J, C.; Lipscomb, J. D. Biochemistry 1996, 35, 10240.
20. (f) Ambundo, E. A.; Friesner, R. A.; Lippard. S. J. J. Am. Chem. Soc. 2002. 124, 8770.
21. Ruzicka, F.; Huang, D. S.; Donnelly, M. I.; Frey, P. A. Biochemistry 1990, 29, 1696.
22. Priestley, N. D.; Floss, H. G.; Froland, W. A.; Lipscomb, J. D.; Williams, P. G.; Morimoto, H. J. Am. Chem. Soc. 1992, 114, 7561.
23. Liu, K. E.; Johnson, C. C.; Newcomb, M.; Lippard, S. J. J. Am. Chem. Soc. 1993, 115, 939.
24. Lee, S. K.; Fox, B. G.; Froland, W. A.; Lipscomb, J. D.; Münck, E. J. Am. Chem. Soc. 1993, 115, 6450.
25. Lee, S. K.; Nesheim, J. C.; Lipscomb, J. D. J. Biol. Chem. 1993, 268, 21569.
26. Choi, S. Y.; Eaton, P. E.; Kopp, D. A.; Lippard, S. J.; Newcomb, M.; Shen, R. N. J. Am. Chem. Soc. 1999, 121, 12198.
27. Valentine, A. M.; Wilkinson, B.; Liu, K. E.; Komar-Panicucci. S.; Priestley, N. D.; Williams, P. G.; Morimoto, H.; Floss, H. G.; Lippard, S. J. J. Am. Chem. Soc. 1997. 119, 1818.
28. Valentine, A. M.; Tavares, P.; Pereira, A. S.; Davydov, R.; Krebs, C.; Koffman, B. M.; Edmondson, D. E.; Huynh, B. H.; Lippard, S. J. J. Am. Chem. Soc. 1998, 120, 2190.
29. Jin. Y.; Lipscomb, J. D. J. Inorg. Biochem. 1999, 74, 182.
30. Jin, Y.; Lipscomb, J. D. Biochemistry 1999, 38, 6178-6186.
31. Jin, Y.; Lipscomb, J, D. J, Biol. Inorg. Chem. 2001, 6, 717.
32. (a) Newcomb, M.; Shen, R. N.; Lu, Y.; Coon, M. J.; Hollenberg, P. F.; Kopp, D. A.; Lippard, S. J. J. Am. Chem. Soc. 2002, 124, 6879.
33. (b) Valentine, A. M.; LeTadic-Biadatti, M. H.; Toy, P. H.; Newcomb, M.; Lippard, S. J. J. Biol. Chem. 1999, 274, 10771.
34. Parr, R. G.; Yang, W. Density Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
35. Ziegler, T. Chem. Rev. 1991, 91, 651.
36. Gherman, B. F.; Dunietz, B. D.; Whittington, D. A.; Lippard, S. J.; Friesner, R. A. J. Am. Chem. Soc. 2001, 123, 3836.
37. Friesner, R. A.; Dunietz, B. D. Acc. Chem. Res. 2001, 34, 351.
38. Dunietz, B. D.; Beachy, M. D.; Cao, Y. X.; Whittington, D. A.; Lippard, S. J.; Friesner, R. A. J. Am. Chem. Soc. 2000, 122, 2828.
39. Guallar, V.; Gherman, B. F.; Miller, W. H.; Lippard, S. J.; Friesner, R. A. J. Am. Chem. Soc. 2002, 124, 3377.
40. Musaev, D. G.; Basch, H.; Morokuma, K. J. Am. Chem. Soc. 2002, 124. 4135.
41. Torrent, M.; Vreven, T.; Musaev, D. G.; Morokuma, K.; Farkas, O.; Schlegel, H. B. J. Am. Chem. Soc. 2002, 124, 192.
42. Torrent, M.; Musaev, D. G.; Basch, H.; Morokuma, K. J. Comput. Chem. 2002, 23, 59.
43. Basch, H.; Musaev, D. G.; Morokuma, K. J. Phys. Chem. B 2001, 105, 8452.
44. Torrent, M.; Mogi, K.; Basch, H.; Musaev, D. G.; Morokuma, K. J. Phys. Chem. B 2001, 105, 8616.
45. Torrent, M.; Musaev, D. G.; Morokuma, K.; Basch, H. J. Phys. Chem. B 2001, 105, 4453.
46. Basch, H.; Musaev, D. G.; Mogi, K.; Morokuma, K. J. Phys. Chem. A 2001, 105, 3615.
47. Torrent, M.; Musaev, D. G.; Morokuma, K. J. Phys. Chem. B 2001, 105, 322.
48. Basch, H.; Mogi, K.; Musaev, D. G.; Morokuma, K. J. Am. Chem. Soc. 1999, 121, 7249.
49. Yoshizawa, K. J. Organomet. Chem. 2001, 635, 100.
50. Yoshizawa, K.; Suzuki, A.; Shiota, Y.; Yamabe, T. Bull. Chem. Soc. Jpn. 2000, 73, 815.
51. Yoshizawa, K. J. Biol. Inorg. Chem. 1998, 3, 318.
52. Yoshizawa, K.; Shiota, Y.; Yamabe, T. J. Am. Chem. Soc. 1998, 120, 564.
53. Yoshizawa, K.; Ohta, T.; Yamabe, T.; Hoffmann, R. J. Am. Chem. Soc. 1997, 119, 12311.
54. Yoshizawa, K.; Yokomichi, Y.; Shiota, Y.; Ohta, T.; Yamabe, T. Chem. Lett. 1997, 587.
55. Yoshizawa, K.; Yamabe, T.; Hoffmann, R. New J. Chem. 1997, 21, 151.
56. Yoshizawa, K.; Hoffmann, R. Inorg. Chem. 1996, 35, 2409.
57. Siegbahn, P. E. M. J. Biol. Inorg. Chem. 2001, 6, 27.
58. Siegbahn, P. E. M.; Crabtree, R. H. J. Am. Chem. Soc. 1997, 119, (9), 3103.
59. Siegbahn, P. E. M. Chem. Phys. Lett. 2002, 351, 311.
60. Siegbahn, P. E. M.; Blomberg, M. R. A. Chem. Rev. 2000, 100, 421.
61. Siegbahn, P. E. M. Inorg. Chem. 1999, 38, 2880.
62. Siegbahn, P. E. M.; Crabtree, R. H.; Nordlund, P. J. Biol. Inorg. Chem. 1998, 3, 314.
63. Lovell, T.; Han, W.-G.; Liu, T.; Noodleman, L. J. Am. Chem. Soc. 2002, 124, 5890.
64. Jaguar 4.1: Schrödinger, Inc., Portland, OR, 2000.
65. Slater, J. C. Quantum Theory of Molecules and Solids, Vol. 4: The Self-Consistent Field for Molecules and Solids; McGraw-Hill: New York, 1974,
66. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
67. Becke, A. D. Phys. Rev. A 1988, 38, 3098.
68. Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
69. Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58 (8), 1200.
70. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270.
71. Wadt, W. R.; Hay, P. J. J. Chem. Phys. 1985, 82, 284.
72. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299.
73. Dunning, T. H. J. Chem. Phys. 1989, 90, 1007.
74. Noodleman, L. J. Chem. Phys. 1981, 74, 5737.
75. Yamaguchi, K.; Jensen, F.; Dorigo, A.; Houk, K. N. Chem. Phys. Lett. 1988, 149, 537.
76. Cotton, F. A. Chemical Applications of Group Theory, 3rd Ed.; John Wiley & Sons: New York, 1990.
77. Baik, M.-H.; Lee, D.; Friesner, R. A.; Lippard, S. J. Isr. J. Chem. 2001, 41, 173.
78. The spin densities of 3.5 on each iron center are indicative of high-spin (S = 2) configurations. A second reasonable possibility is an intermediate-spin (S = 1) state with only half of the four d-electrons unpaired on each metal center. A recent computational study (ref 55) has shown that the S = I spin state of the antiferromagnetically coupled Q is 7.53 kcal/mol higher in energy than the S = 2 state. This result is in good agreement with typical values found in exploratory calculations for our large-scale model. Thus. this alternative is not further considered.
79. Hroyat, D. A.; Borden, W. T. J. Am. Chem. Soc. 1994, 116, 6459.
80. Fukui, K. Science 1982, 218, 747.
81. Fukui, K.; Koga, N.; Fujimoto, H. J. Am. Chem. Soc. 1981, 103, 196.
82. Hoffmann, R.; Imamura, A.; Zeiss, G. D. J. Am. Chem. Soc. 1967, 89, 5215.
83. Woodward, R. B.; Hoffmann, R. J. Am. Chem. Soc. 1965, 87, 395.
84. Page 99 in ref 26.
85. Baik, M.-H.; Ziegler, T.; Schauer, C. K. J. Am. Chem. Soc. 2000, 122, 9143.
86. Baik, M.-H.; Schauer, C. K.; Ziegler, T. J. Am. Chem. Soc. 2002, 124, 11167.
87. This interesting relationship between structure and reactivity might be an exploitable design feature. A more detailed quantitative analysis of the chemical difference between O3 and O4 is not helpful for this paper and will be presented elsewhere together with a possible exploitation strategy in synthetic models.
88. z. These two orbitals are chosen because they have the right phase to promote the electron transfer.
89. SHE, the potential referenced to standard hydrogen electrode (SHE), by subtracting the experimentally determined absolute potential of SHE (Reiss, H.; Heller, A. J. Phys. Chem. 1985, 89, 4207.).
90. SHE, the potential referenced to standard hydrogen electrode (SHE), by subtracting the experimentally determined absolute potential of SHE (Reiss, H.; Heller, A. J. Phys. Chem. 1985, 89, 4207.).