Characterization of the structure and reactivity of monocopper-oxygen complexes supported by β-diketiminate and anilido-imine ligands

Journal of Computational Chemistry

Volumn 27, Issue 16, 2006, Pages 1950-1961

  Gherman, Benjamin F ^a   Tolman, William B ^a   Cramer, Christopher J ^a  

^a University of Minnesota   (United States)

Author keywords

Biomimetic copper oxygen complexes; C H bond activation; Density functional theory; Oxygen activation

Indexed keywords

ADDUCTS; BIOMIMETIC MODELS; PEPTIDYLGLYCINE HYDROXYLATING MONOOXYGENASE (PHM);

CHEMICAL ACTIVATION; CHEMICAL BONDS; COMPLEXATION; ENZYME KINETICS; MATHEMATICAL MODELS; PROBABILITY DENSITY FUNCTION;

COPPER;

COPPER; DOPAMINE BETA MONOOXYGENASE; IMINE; LIGAND; MIXED FUNCTION OXIDASE; MULTIENZYME COMPLEX; ORGANOMETALLIC COMPOUND; OXYGEN; PEPTIDYLGLYCINE MONOOXYGENASE;

ARTICLE; BINDING SITE; CATALYSIS; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; COMPUTER SIMULATION; CONFORMATION; SYNTHESIS;

BINDING SITES; CATALYSIS; COMPUTER SIMULATION; COPPER; DOPAMINE BETA-HYDROXYLASE; IMINES; LIGANDS; MIXED FUNCTION OXYGENASES; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MULTIENZYME COMPLEXES; ORGANOMETALLIC COMPOUNDS; OXYGEN;

EID: 33751251980     PISSN: 01928651     EISSN: 1096987X     Source Type: Journal    
DOI: 10.1002/jcc.20502     Document Type: Article

References (73)

1. Solomon, E. I.; Sundaram, U. M.; Machonkin, T. E. Chem Rev 1996, 96, 2563.
2. Solomon, E. I.; Chen, P.; Metz, M.; Lee, S. K.; Palmer, A. E. Angew Chem Int Ed Engl 2001, 40, 4570.
3. Klinman, J. P. Chem Rev 1996, 96, 2541.
4. Stewart, L. C.; Klinman, J. P. Annu Rev Biochem 1988, 57, 551.
5. Eipper, B. A.; Stoffers, D. A.; Mains, R. E. Annu Rev Neurosci 1992, 15, 57.
6. McMahon, A.; Geertman, R.; Sabban, E. L. J Neurosci Res 1990, 25, 395.
7. Stoffers, D. A.; Green, C. B.; Eipper, B. A. Proc Natl Acad Sci USA 1989, 86, 735.
8. Tian, G. C.; Berry, J. A.; Klinman, J. P. Biochemistry 1994, 33, 226.
9. Evans, J. P.; Ahn, K.; Klinman, J. P. J Biol Chem 2003, 278, 49691.
10. Prigge, S. T.; Kolhekar, A. S.; Eipper, B. A.; Mains, R. E.; Amzel, L. M. Science 1997, 278, 1300.
11. Prigge, S. T.; Kolhekar, A. S.; Eipper, B. A.; Mains, R. E.; Amzel, L. M. Nat Struct Biol 1999, 6, 976.
12. Prigge, S. T.; Eipper, B. A.; Mains, R. E.; Amzel, L. M. Science 2004, 304, 864.
13. Gherman, B. F.; Heppner, D. E.; Tolman, W. B.; Cramer, C. J. J Biol Inorg Chem 2006, 11, 197.
14. Kamachi, T.; Kihara, N.; Shiota, Y.; Yoshizawa, K. Inorg Chem 2005, 44, 4226.
15. Yoshizawa, K.; Kihara, N.; Kamachi, T.; Shiota, Y. Inorg Chem 2006, 45, 3034.
16. Francisco, W. A.; Blackburn, N. J.; Klinman, J. P. Biochemistry 2003, 42, 1813.
17. Chen, P.; Bell, J.; Eipper, B. A.; Solomon, E. I. Biochemistry 2004, 43, 5735.
18. Chen, P.; Solomon, E. I. J Am Chem Soc 2004, 126, 4991.
19. Lewis, E. A.; Tolman, W. B. Chem Rev 2004, 104, 1047.
20. Johansson, A. J.; Blomberg, M. R. A.; Siegbahn, P. E. M. Inorg Chem 2006, 45, 1491.
21. Smirnov, V. V.; Roth, J. P. J Am Chem Soc 2006, 128, 3683.
22. Schatz, M.; Raab, V.; Foxon, S. P.; Brehm, G.; Schneider, S.; Reiher, M.; Holthausen, M. C.; Sundermeyer, J.; Schindler, S. Angew Chem Int Ed Engl 2004, 43, 4360.
23. Cheruzel, L. E.; Cecil, M. R.; Edison, S. E.; Mashuta, M. S.; Baldwin, M. J.; Buchanan, R. M. Inorg Chem 2006, 45, 3191.
24. Blackburn, N. J.; Hasnain, S. S.; Pettingill, T. M.; Strange, R. W. J Biol Chem 1991, 266, 23120.
25. Reedy, B. J.; Blackburn, N. J. J Am Chem Soc 1994, 116, 1924.
26. Boswell, J. S.; Reedy, B. J.; Kulathila, R.; Merkler, D.; Blackburn, N. J. Biochemistry 1996, 35, 12241.
27. Kolhekar, A. S.; Keutmann, H. T.; Mains, R. E.; Quon, A. S. W.; Eipper, B. A. Biochemistry 1997, 36, 10901.
28. Aboelella, N. W.; Kryatov, S. V.; Gherman, B. F.; Brennessel, W. W.; Young, V. G., Jr.; Sarangi, R.; Rybak-Akimova, E. V.; Hodgson, K. O.; Hedman, B.; Solomon, E. L; Cramer, C. J.; Tolman, W. B. J Am Chem Soc 2004, 126, 16896.
29. Reynolds, A. M.; Gherman, B. F.; Cramer, C. J.; Tolman, W. B. Inorg Chem 2005, 44, 6989.
30. Reynolds, A. M.; Lewis, E. A.; Aboelella, N. W.; Tolman, W. B. Chem Commun 2005, 2014.
31. Schrodinger, LLC. Jaguar 5.0; Schrodinger, LLC, Portland, OR, 2002.
32. Johnson, B. G.; Gill, P. M. W.; Pople, J. A. J Chem Phys 1993, 98, 5612.
33. Becke, A. D. J Chem Phys 1993, 98, 1372.
34. Lee, C. T.; Yang, W. T.; Parr, R. G. Phys Rev B 1988, 37, 785.
35. Ducere, J.-M.; Goursot, A.; Berthomieu, D. J Phys Chem A 2005, 109, 400.
36. Gherman, B. F.; Cramer, C. J. Inorg Chem 2004, 43, 7281.
37. Aboelella, N. W.; Gherman, B. F.; Hill, L. M.; York, J. T.; Holm, N.; Young, V. G., Jr.; Cramer, C. J.; Tolman, W. B. J Am Chem Soc 2006, 128, 3345.
38. Hay, P. J.; Wadt, W. R. J Chem Phys 1985, 82, 270.
39. Wadt, W. R.; Hay, P. J. J Chem Phys 1985, 82, 284.
40. Hay, P. J.; Wadt, W. R. J Chem Phys 1985, 82, 299.
41. Peng, C. Y.; Schlegel, H. B. Isr J Chem 1993, 33, 449.
42. Glendening, E. D.; Badenhoop, J. K.; Reed, A. E.; Carpenter, J. E.; Bohmann, J. A.; Morales, C. M.; Weinhold, F. NBO 5.0.; Theoretical Chemistry Institute, University of Wisconsin, Madison, WI, 2001. http://www.chem.wisc.edu/ ~nbo5
43. Friesner, R. A.; Baik, M.-H.; Guallar, V.; Gherman, B. F.; Wirstam, M.; Murphy, R. B.; Lippard, S. J Coord Chem Rev 2003, 238/239, 267.
44. Baik, M.-H.; Newcomb, M.; Friesner, R. A.; Lippard, S. J. Chem Rev 2003, 103, 2385.
45. Scott, A. P.; Radom, L. J Phys Chem 1996, 100, 16502.
46. Marten, B.; Kim, K.; Cortis, C.; Friesner, R. A.; Murphy, R. B.; Ringnalda, M. N.; Sitkoff, D.; Honig, B. J Phys Chem 1996, 100, 11775.
47. Tannor, D. J.; Marten, B.; Murphy, R.; Friesner, R. A.; Sitkoff, D.; Nicholls, A.; Ringnalda, M.; Goddard, W. A.; Honig, B. J Am Chem Soc 1994, 116, 11875.
48. Carvajal, C.; Tolle, K. J.; Smid, J.; Szwarc, M. J Am Chem Soc 1965, 87, 5548.
49. Metz, D. J.; Glines, A. J Phys Chem 1967, 71, 1158.
50. Cramer, C. J. Essentials of Computational Chemistry. Theories and Models, 2nd ed.; Wiley: West Sussex, England, 2004.
51. Tissandier, M. D.; Cowen, K. A.; Feng, W. Y.; Gundlach, E.; Cohen, M. H.; Earhart, A. D.; Coe, J. V.; Tuttle, T. R. J Phys Chem A 1998, 102, 7787.
52. Kelly, C. P.; Cramer, C. J.; Truhlar, D. G. J Phys Chem B (in press).
53. Ribas, X.; Jackson, D. A.; Donnadieu, B.; Mahia, J.; Parella, T.; Xifra, R.; Hedman, B.; Hodgson, K. O.; Llobet, A.; Stack, T. D. P. Angew Chem Int Ed Engl 2002, 41, 2991.
54. Winget, P.; Cramer, C. J.; Truhlar, D. G. Theor Chem Accounts 2004, 112, 217.
55. Lide, D. R. Handbook of Chemistry and Physics, 85th ed.; CRC: Boca Raton, 2004.
56. Andersson, K.; Malmqvist, P. A.; Roos, B. O. J Chem Phys 1992, 96, 1218.
57. Karlstrom, G.; Lindh, R.; Malmqvist, P. A.; Roos, B. O.; Ryde, U.; Veryazov, V.; Widmark, P. O.; Cossi, M.; Schimmelpfennig, B.; Neogrady, P.; Seijo, L. Comput Matl Sci 2003, 28, 222.
58. Barandiaran, Z.; Seijo, L. Can J Chem 1992, 70, 409.
59. Pierloot, K.; Dumez, B.; Widmark, P. O.; Roos, B. O. Theor Chim Acta 1995, 90, 87.
60. Binkley, J. S.; Pople, J. A.; Hehre, W. J. J Am Chem Soc 1980, 102, 939.
61. Hehre, W. J.; Stewart, R. F.; Pople, J. A. J Chem Phys 1969, 51, 2657.
62. Mayer, J. M. Comments Inorg Chem 1988, 8, 125.
63. Mayer, J. M. Inorg Chem 1988, 27, 3899.
64. Griffith, W. P. Coord Chem Rev 1970, 5, 459.
65. Kitajima, N.; Koda, T.; Iwata, Y.; Morooka, Y. J Am Chem Soc 1990, 112, 8833.
66. Kitajima, N.; Morooka, Y. Chem Rev 1994, 94, 737.
67. Vaska, L. Accounts Chem Res 1976, 9, 175.
68. Whitham, C. J.; Ozeki, H.; Saito, S. J Chem Phys 2000, 112, 641.
69. Ikeda, S.; Nakajima, T.; Hirao, K. Mol Phys 2003, 101, 105.
70. Mayer, J. M. Accounts Chem Res 1998, 31, 441.
71. Francisco, W. A.; Knapp, M. J.; Blackburn, N. J.; Klinman, J. P. J Am Chem Soc 2002, 124, 8194.
72. Miller, S. M.; Klinman, J. P. Biochemistry 1985, 24, 2114.
73. Freeman, J. C.; Villafranca, J. J.; Merkler, D. J. J Am Chem Soc 1993, 115, 4923.