Theoretical models on the Cu 2O 2 torture track: Mechanistic implications for oxytyrosinase and small-molecule analogues

Journal of Physical Chemistry A

Volumn 110, Issue 5, 2006, Pages 1991-2004

  Cramer, Christopher J ^a   Włoch, Marta ^b   Piecuch, Piotr ^b   Puzzarini, Cristina ^c   Gagliardi, Laura ^d  

^a UNIVERSITY OF MINNESOTA   (United States)

^b MICHIGAN STATE UNIVERSITY   (United States)

^c UNIVERSITY OF BOLOGNA   (Italy)

^d UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRON CORRELATION; HARTREE-FOCK EXCHANGE; ISOMERIZATION COORDINATE;

CHEMICAL BONDS; ISOMERS; MATHEMATICAL MODELS; PERTURBATION TECHNIQUES; PROBABILITY DENSITY FUNCTION; STABILITY;

COPPER OXIDES;

COPPER; CUPRIC OXIDE; MONOPHENOL MONOOXYGENASE;

ARTICLE; BINDING SITE; CHEMICAL STRUCTURE; CHEMISTRY; ISOMERISM;

BINDING SITES; COPPER; ISOMERISM; MODELS, MOLECULAR; MONOPHENOL MONOOXYGENASE;

EID: 33644804094     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp056791e     Document Type: Article

References (101)

1. Solomon, E. I.; Baldwin, M. J.; Lowery, M. D. Chem. Rev. 1992, 92, 521.
2. Kitajima, N.; Moro-oka, Y. Chem. Rev. 1994, 94, 737.
3. 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; p 188.
4. Kaim, W.; Rail, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 43.
5. Klinman, J. P. Chem. Rev. 1996, 96, 2541.
6. Solomon, E. I.; Sundaram, U. M.; Machonkin, T. E. Chem. Rev. 1996, 96, 2563.
7. Solomon, E. I.; Chen, P.; Metz, M.; Lee, S.-K.; Palmer, A. E. Angew. Chem., Int. Ed. 2001, 40, 4570.
8. Gamez, P.; Koval, I. A.; Reedijk, J. Dalton Trans. 2004, 4079.
9. Decker, H.; Dillinger, R.; Tuczek, F. Angew. Chem., Int. Ed. 2000, 39, 1591.
10. Solomon, E. I.; Tuczek, F.; Root, D. E.; Brown, C. A. Chem. Rev. 1994, 94, 827.
11. Tolman, W. B. Acc. Chem. Res. 1997, 30, 227.
12. Mirica, L. M.; Ottenwaelder, X.; Stack, T. D. P. Chem. Rev. 2004, 104, 1013.
13. Lewis, E. A.; Tolman, W. B. Chem. Rev. 2004, 104, 1047.
14. Cole, A. P.; Mahadevan, V.; Mirica, L. M.; Ottenwaelder, X.; Stack, T. D. P. Inorg. Chem. 2005, 44, 7345.
15. Stack, T. D. P. Dalton Trans. 2003, 1881.
16. Jung, B.; Karlin, K. D.; Zuberbühler, A. D. J. Am. Chem. Soc. 1996, 118, 3763.
17. Holland, P. L.; Tolman, W. B. Coord. Chem. Rev. 1999, 192, 855.
18. Magnus, K. A.; Ton-That, H.; Carpenter, J. E. Chem. Rev. 1994, 94, 111.
19. Magnus, K. A.; Hazes, B.; Ton-That, H.; Bonaventura, C.; Bonaventura, J.; Hol, W. G. J. Proteins: Struct., Funct., Genet. 1994, 19, 302.
20. Cahoy, J.; Holland, P. L.; Tolman, W. B. Inorg. Chem. 1999, 38, 2161.
21. Que, L.; Tolman, W. B. Angew. Chem., Int. Ed. 2002, 41, 1114.
22. Pidcock, E.; DeBeer, S.; Obias, H. V.; Hedman, B.; Hodgson, K. O.; Karlin, K. D.; Solomon, E. I. J. Am. Chem. Soc. 1999, 121, 1870.
23. Liang, H.-C.; Zhang, C. X.; Henson, M. J.; Sommer, R. D.; Hatwell, K. R.; Kaderli, S.; Zuberbühle, A. D.; Rheingold, A. L.; Solomon, E. I.; Karlin, K. D. J. Am. Chem. Soc. 2002, 124, 4170.
24. Henson, M. J.; Vance, M. A.; Zhang, C. X.; Liang, H. C.; Karlin, K. D.; Solomon, E. I. J. Am. Chem. Soc. 2003, 125, 5186.
25. Mizuno, M.; Hayashi, H.; Fujinami, S.; Furutachi, H.; Nagatomo, S.; Otake, S.; Uozumi, K.; Suzuki, M.; Kitagawa, T. Inorg. Chem. 2003, 42, 8534.
26. Liang, H. C.; Henson, M. J.; Hatcher, L. Q.; Vance, M. A.; Zhang, C. X.; Lahti, D.; Kaderli, S.; Sommer, R. D.; Rheingold, A. L.; Zuberbuhler, A. D.; Solomon, E. I.; Karlin, K. D. Inorg. Chem. 2004, 43, 4115.
27. Cramer, C. J.; Smith, B. A.; Tolman, W. B. J. Am. Chem. Soc. 1996, 118, 11283.
28. Bérces, A. Inorg. Chem. 1997, 36, 4831.
29. Yoshizawa, K.; Ohta, T.; Yamabe, T. Bull. Chem.-Soc. Jpn. 1997, 70, 1911.
30. Flock, M.; Pierloot, K. J. Phys. Chem. A 1999, 103, 95.
31. Lam, B. M. T.; Halfen, J. A.; Young, V. G., Jr.; Hagadorn, J. R.; Holland, P. L.; Lledos, A.; Cucurull-Sanchez, L.; Novoa, J. J.; Alvarez, S.; Tolman, W. B. Inorg. Chem. 2000, 39, 4059.
32. Henson, M. J.; Mukherjee, P.; Root, D. E.; Stack, T. D. P.; Solomon, E. I. J. Am. Chem. Soc. 1999, 121, 10332.
33. Siegbahn, P. E. M. J. Biol. Inorg. Chem. 2003, 8, 577.
34. Rode, M. F.; Werner, H.-J. Theor. Chem. Acc. 2005, 114, 309.
35. Steinfeld, J. I.; Francisco, J. S.; Hase, W. L. Chemical Kinetics and Dynamics, 2nd ed.; Prentice Hall: New York, 1999.
36. Hatcher, L. Q.; Karlin, K. D. J. Biol. Inorg. Chem. 2004, 9, 669.
37. Cramer, C. J.; Pak, Y. Theor. Chem. Acc. 2001, 105, 477.
38. Cramer, C. J.; Kinsinger, C. K.; Pak, Y. J. Mol. Struct. (THEOCHEM) 2003, 632, 111.
39. Spuhler, P.; Holthausen, M. C. Angew. Chem., Int. Ed. 2003, 42, 5961.
40. Mirica, L. M.; Vance, M.; Rudd, D. J.; Hedman, B.; Hodgson, K. O.; Solomon, E. I.; Stack, T. D. P. Science 2005, 308, 1890.
41. Lind, T.; Siegbahn, P. E. M.; Crabtree, R. H. J. Phys. Chem. B 1999, 103, 1193.
42. Siegbahn, P. E. M.; Wirstam, M. J. Am. Chem. Soc. 2001, 123, 11819.
43. Siegbahn, P. E. M. J. Biol. Inorg. Chem. 2003, 8, 567.
44. Dolg, M.; Wedig, U.; Stoll, H.; Preuss, H. J. Chem. Phys. 1987, 86, 866.
45. Pierloot, K.; Dumez, B.; Widmark, P.-O.; Roos, B. O. Theor. Chim. Acta 1995, 90, 87.
46. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986.
47. Easton, R. E.; Giesen, D. J.; Welch, A.; Cramer, C. J.; Truhlar, D. G. Theor. Chim. Acta 1996, 93, 281.
48. Becke, A. D. Phys. Rev. A 1988, 38, 3098.
49. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
50. Perdew, J. P. In Electronic Structure of Solids '91; Ziesche, P., Eschrig, H., Eds.; Akademie Verlag: Berlin, 1991; p 11.
51. Perdew, J.; Wang, Y. Phys. Rev. B 1992, 45, 13244.
52. Adamo, C.; Barone, V. J. Chem. Phys. 1998, 108, 664.
53. Tao, J.; Perdew, J. P.; Staroverov, V. N.; Scuseria, G. E. Phys. Rev. Lett. 2003, 91, 146401.
54. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
55. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623.
56. Lynch, B. J.; Fast, P. L.; Harris, M.; Truhlar, D. G. J. Phys. Chem. A 2000, 104, 4811.
57. Staroverov, V. N.; Scuseria, G. E.; Tao, J.; Perdew, J. P. J. Chem. Phys. 2003, 119, 12129.
58. Cramer, C. J. Essentials of Computational Chemistry, 2nd ed.; John Wiley & Sons: Chichester, UK, 2004.
59. Ziegler, T.; Rauk, A.; Baerends, E. J. Theor. Chim. Acta 1977, 43, 261.
60. Yamaguchi, K.; Jensen, F.; Dorigo, A.; Houk, K. N. Chem. Phys. Lett. 1988, 149, 537.
61. Lim, M. H.; Worthington, S. E.; Dulles, F. J.; Cramer, C. J. In Chemical Applications of Density Functional Theory; Laird, B. B., Ross, R. B., Ziegler, T., Eds.; American Chemical Society: Washington, DC, 1996; Vol. 629, p 402.
62. Isobe, H.; Takano, Y.; Kitagawa, Y.; Kawakami, T.; Yamanaka, S.; Yamaguchi, K.; Houk, K. N. Mol. Phys. 2002, 100, 717.
63. Gräfenstein, J.; Cremer, D. Mol. Phys. 2001, 99, 981.
64. Čížek, J. J. Chem. Phys. 1966, 45, 4256.
65. Čížek, J. Adv. Chem. Phys. 1969, 14, 35.
66. Purvis, G. D.; Bartlett, R. J. J. Chem. Phys. 1982, 76, 1910.
67. Scuseria, G. E.; Scheiner, A. C.; Lee, T. J.; Rice, J. E.; Schaefer, H. F., III. J. Chem. Phys. 1987, 86, 2881.
68. Piecuch, P.; Paldus, J. Int. J. Quantum Chem. 1989, 36, 429.
69. Raghavachari, K.; Trucks, G. W.; Pople, J. A.; Head-Gordon, M. Chem. Phys. Lett. 1989, 157, 479.
70. Kowalski, K.; Piecuch, P. J. Chem. Phys. 2000, 113, 5644.
71. Özkan, I.; Kinal, A.; Balci, M. J. Phys. Chem. A 2004, 108, 507.
72. McGuire, M. J.; Piecuch, P. J. Am. Chem. Soc. 2005, 127, 2608.
73. Kinal, A.; Piecuch, P. J. Phys. Chem. A 2006, in press.
74. Piecuch, P.; Kowalski, K. In Computational Chemistry: Reviews of Current Trends; Leszczyn ski, J., Ed.: World Scientific: Singapore, 2000; Vol. 5, p 1.
75. Kowalski, K.; Piecuch, P. J. Chem. Phys. 2000, 113, 18.
76. Kowalski, K.; Piecuch, P. Chem. Phys. Lett. 2001, 344, 165.
77. Piecuch, P.; Kucharski, S. A.: Špirko, V.; Kowalski, K. J. Chem. Phys. 2001, 115, 5796.
78. McGuire, M. J.; Kowalski, K.; Piecuch, P. J. Chem. Phys. 2002, 117, 3617.
79. McGuire, M. J.; Piecuch, P.; Kowalski, K.; Kucharski, S. A.; Musiał, M. J. Phys. Chem. A 2004, 108, 8878.
80. Kowalski, K.; Piecuch, P. J. Chem. Phys. 2005, 122, 074107.
81. Piecuch, P.; Kowalski, K.; Pimienta, I. S. O.; Kucharski, S. A. In Low-Lying Potential Energy Surfaces; Hoffmann, M. R., Dyall, K. G., Eds.; American Chemical Society: Washington, DC, 2002; Vol. 828, p 31.
82. Piecuch, P.; Kowalski, K.; Pimienta, I. S. O.; McGuire, M. J. Int. Rev. Phys. Chem. 2002, 21, 527.
83. Piecuch, P.; Pimienta, I. S. O.; Fan, P.-D.; Kowalski, K. In Progress in Theoretical Chemistry and Physics; Maruani, J., Lefebvre, R., Brändas, E., Eds.; Kluwer: Dordrecht, Netherlands, 2003; Vol. 12, p 119.
84. Piecuch, P.; Kowalski, K.; Pimienta, I. S. O.; Fan, P.-D.; Lodriguito, M.; McGuire, M. J.; Kucharski, S. A.; Kuś, T.; Musiał, M. Theor. Chem. Acc. 2004, 112, 349.
85. Piecuch, P.; Włoch, M.; Lodriguito, M.; Gour, J. R. In Progress in Theoretical Chemistry and Physics; Wilson, S., Julien, J.-P., Maruani, J., Brändas, E., Delgado-Barrio, G., Eds.; Springer: Berlin, 2006, in press; Vol. 15.
86. Piecuch, P.; Włoch, M. J. Chem. Phys. 2005, 123, 224105.
87. Piecuch, P.; Włoch, M.; Gour, J. R.; Kinal, A. Chem. Phys. Lett. 2005, 418, 463.
88. Roos, B. O. In Ab Initio Methods in Quantum Chemistry; Lawley, K. P., Ed.; Wiley: New York, 1987; Vol. 2, p 399.
89. Andersson, K.; Malmqvist, P.-Å.; Roos, B. O.; Sadlej, A. J.; Wolinski, K. J. Phys. Chem. 1990, 94, 5483.
90. Persson, B. J.; Roos, B. O.; Pierloot, K. J. Chem. Phys. 1994, 101, 6810.
91. Gagliardi, L.; Roos, B. O. Inorg. Chem. 2003, 42, 1599.
92. Ghosh, A.; Taylor, P. R. Curr. Opin. Chem. Biol. 2003, 7, 113.
93. Roos, B. O.; Andersson, K.; Fülscher, M. P.; Serrano-Andrés, L.; Pierloot, K.; Merchán, M.; Molina, V. J. Mol. Struct. (THEOCHEM) 1996, 388, 257.
94. Ghigo, G.; Roos, B. O.; Malmqvist, P.-Å. Chem. Phys. Lett. 2004, 396, 142.
95. Siegbahn, P. E. M. Quart. Rev. Biophys. 2003, 36, 91.
96. Finley, J.; Malmqvist, P.-Å.; Roos, B. O.; Serrano-Andres, L. Chem. Phys. Lett. 1998, 288, 299.
97. Roos, B. O., personal communication.
98. He, Y.; Gräfenstein, J.; Kraka, E.; Cremer, D. Mol. Phys. 2000, 98, 1639.
99. Polo, V.; Kraka, E.; Cremer, D. Theor. Chem. Acc. 2002, 107, 291.
100. Gräfenstein, J.; Kraka, E.; Filatov, M.; Cremer, D. Int. J. Mol. Sci. 2002, 3, 360.
101. Gräfenstein, J.; Cremer, D. Mol. Phys. 2005, 103, 279.