Theoretical exploration of the oxidative properties of a [ (tren Me1) CuO2]+ adduct relevant to copper monooxygenase enzymes: Insights into competitive dehydrogenation versus hydroxylation reaction pathways

Chemistry - A European Journal

Volumn 14, Issue 21, 2008, Pages 6465-6473

  De La Lande, Aurélien ^a,b   Parisel, Olivier ^a   Gérard, Hélène ^a   Moliner, Vicente ^b   Reinaud, Olivia ^c  

^a LABORATOIRE DE CHIMIE THÉORIQUE   (France)

^b UNIVERSITAT JAUME I   (Spain)

^c UNIVERSITÉ PARIS DESCARTES   (France)

Author keywords

Copper; Density functional calculations; Dioxygen; Enzyme models; Hydroxylation; Oxidation

Indexed keywords

DISCRETE FOURIER TRANSFORMS; DENSITY FUNCTIONAL THEORY; HYDROXYLATION; OXIDATION;

COPPER; DENSITY FUNCTIONAL CALCULATIONS; DIOXYGEN; ENZYME MODELS; HYDROXYLATION; OXIDATION;

PROBABILITY DENSITY FUNCTION; COPPER;

DIOXYGENS; ENZYME MODELS; HYDROXYLATION REACTIONS; MONOOXYGENASE ENZYMES; OXIDATIVE PROPERTIES;

(BIS(AMINOETHYL)(METHYLAMINOETHYL)AMMINE)COPPER(I); CARBON; COPPER; HYDROGEN; HYDROGEN PEROXIDE; MIXED FUNCTION OXIDASE; NITROGEN; ORGANOMETALLIC COMPOUND;

ARTICLE; CHEMISTRY; ELECTRON; HYDROXYLATION; METABOLISM; OXIDATION REDUCTION REACTION; QUANTUM THEORY;

CARBON; COPPER; ELECTRONS; HYDROGEN; HYDROGEN PEROXIDE; HYDROXYLATION; MIXED FUNCTION OXYGENASES; NITROGEN; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; QUANTUM THEORY;

EID: 53849084796     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200701595     Document Type: Article

References (72)

1. T. Punniyamurthy, S. Velusamy, J. Iqbal, Chem. Rev. 2005, 105, 2329.
2. a) C. Limberg, Angew. Chem. 2003, 115, 6112;
3. Angew. Chem. Int. Ed. 2003, 42, 5932.
4. A. E. Shilov, G. B. Shul'pin, Chem. Rev. 1997, 97, 2879.
5. C. J. Cramer, W. B. Tolman, Acc. Chem. Res. 2007, 40, 601.
6. S. Itoh, Curr. Opin. Chem. Biol. 2006, 10, 115.
7. "Biological Reactions of Dioxygen: An Introduction": R. Y. N. Ho, J. F. Liebman, J. Seiverstone Valentine in Active Oxygen in Biochemistry, Search Series, Vol.3 (Eds.: J. Selverstone Valentine, C. S. Foote, A. Greenberg, J. F. Liebman), Blackie, Glasgow, 1995.
8. J. P. Klinman, J. Biol. Inorg. Chem. 2001, 6, 1.
9. S. Schindler, Eur. J. Inorg. Chem. 2000, 2311.
10. W. B. Tolman, J. Biol. Inorg. Chem. 2006, 11, 261.
11. E. A. Lewis, W. B. Tolman, Chem. Rev. 2004, 104, 1047.
12. J. M. Bollinger, Jr., C. Krebs, Curr. Opin. Chem. Biol. 2007, 11, 151.
13. M. P. Lanci, V. V. Smirnov, C. J. Cramer, E. V. Gauchenova, J. Sundermeyer, J. P. Roth, J. Am. Chem. Soc. 2007, 129, 14697.
14. P. Chen, E. I. Solomon, J. Am. Chem. Soc. 2004, 126, 4991.
15. A. Crespo, M. A. Marti, A. E. Roilberg, L. M. Amzel, D. A. Estrin, J. Am. Chem. Soc. 2006, 128, 12817.
16. T. Kamachi, N. Kihara, Y. Shiota, K. Yoshizawa, Inorg. Chem. 2005, 44, 4226.
17. K. Yoshizawa, N. Kihara, T. Kamachi, Y. Shiota, Inorg. Chem. 2006, 45, 3034.
18. A. Decker, E. I. Solomon, Curr. Opin. Chem. Biol. 2005, 9, 152.
19. L. Q. Hatcher, K. D. Karlin, J. Biol. Inorg. Chem. 2004, 9, 669.
20. L. M. Mirica, X. Ottenwaelder, T. D. P. Slack, Chem. Rev. 2004, 104, 1013.
21. B. F. Gherman, C. J. Cramer, Inorg. Chem. 2004, 43, 7281 and Supporting Information.
22. M. P. Lanci, J. P. Roth, J. Am. Chem. Soc. 2006, 128, 16006.
23. V. V. Smirnov, J. P. Roth, J. Am. Chem. Soc. 2006, 128, 3683.
24. A. T. Bauman, E. T. Yukl, K. Alkevich, A. L. McCormack, N. J. Blackburn, J. Biol. Chem. 2006, 281, 4190.
25. S. T. Prigge, B. A. Eipper, R. E. Mainz, L. M. Amzel, Science 2004, 304, 864.
26. J. P. Klinman, J. Biol. Chem. 2006, 281, 3013.
27. J. Roth, Curr. Opin. Chem. Biol. 2007, 11, 142.
28. P. Chen, E. I. Solomon, Proc. Natl. Acad. Sci. USA 2004, 101, 13105.
29. L. Q. Hatcher, K. D. Karlin, J. Biol. Inorg. Chem. 2004, 9, 669.
30. J. T. York, V. G. Young, W. B. Tolman, Inorg. Chem. 2006, 45, 4191.
31. B. F. Gherman, C. J. Cramer, Coord. Chem. Rev., DOI: 10.1016/j.ccr.2007.11.018.
32. A. M. Reynolds, E. A. Lewis, N. W. Aboelella, W. B. Tolman, Chem. Commun. 2005, 2014.
33. B. F. Gherman, W. B. Tolman, C. J. Cramer, J. Comput. Chem. 2006, 27, 1950.
34. D. J. E. Spencer, N. W. Aboelella, A. M. Reynolds, P. L. Holland, W. B. Tolman, J. Am. Chem. Soc. 2002, 124, 2108.
35. N. W. Aboelella, E. A. Lewis, A. M. Reynolds, W. W. Brennessel, C. J. Cramer, W. B. Tolman, J. Am. Chem. Soc. 2002, 124, 10660.
36. A. M. Reynolds, B. F. Gherman, C. J. Cramer, W. B. Tolman, Inorg. Chem. 2005, 44, 6989.
37. D. Maiti, A. N. Sarjeant, K. D. Karlin, J. Am. Chem. Soc 2007, 129, 6720.
38. D. Maiti, H. R. Lucas, A. N. Sarjeant, K. D. Karlin, J. Am. Chem. Soc. 2007, 129, 6998.
39. D. Maiti, H. C. Fry, J. S. Woertink, M. A. Vance, E. I. Solomon, K. D. Karlin, J. Am. Chem. Soc. 2007, 129, 264.
40. G. Izzet, M.-N. Rager, O. Reinaud, Dalton Trans. 2007, 771;
41. G. Izzet, PhD thesis, University Paris 11, December, 2004.
42. N. W. Aboelella, S. V. Kryatov, B. F. Gherman, W. W. Brennessel, V. G. Young, Jr., R. Sarangi, E. V. Rybak-Akimova, K. O. Hodgson, B. Hedman, E. I. Solomon, C. J. Cramer, W. B. Tolman, J. Am. Chem. Soc. 2004, 126, 16896.
43. A. de la Lande, H. Gérard, V. Moliner, G. Izzet, O. Reinaud, O. Parisel, J. Biol. Inorg. Chem. 2006, 11, 593.
44. J.-P. Piquemal, A. Marquez, O. Parisel, C. Giessner-Prettre, J. Comput. Chem. 2005, 26, 1052.
45. A. de la Lande, V. Moliner, O. Parisel, J. Chem. Phys. 2007, 126, 035102.
46. See Supporting Information.
47. C. Würtele, E. Gaoutchenova, K. Harms, M. C. Holthausen, J. Sundermeyer, S. Schindler, Angew. Chem. 2006, 118, 3951;
48. Angew. Chem. Int. Ed. 2006, 45, 3867.
49. Note that it was checked by means of SF-TDDFT geometry optimizations that the open-shell determinants have almost no influence on the structure of D (see Supporting Information and especially Table S2).
50. A. R. Rossi, R. Hoffmann, Inorg. Chem. 1975, 14, 365.
51. X. L. Huang, J. J. Dannenberg, J. Org. Chem. 1991, 56, 5421.
52. W. A. Francisco, M. J. Knapp, N. J. Blackburn, J. P. Klinman, J. Am. Chem. Soc. 2002, 124, 8194.
53. J. McCracken, P. R. Desai, N. J. Papadopoulos, J. J. Villafranca, J. Peisach, Biochemistry 1988, 27, 4133.
54. M. C. Brenner, J. P. Klinman. Biochemistry 1989, 28, 4664.
55. H. E. de La Mare, J. K. Kochi, F. F. Rust, J. Am. Chem. Soc. 1963, 85, 1437.
56. J. K. Kochi, Science 1967, 155, 415.
57. C. Walling, Acc. Chem. Res. 1915, 8, 125.
58. B. C. Gilbert, J. R. Lindsay Smith, P. Taylor, S. Ward, A. C. Whitwood, J. Chem. Soc. Perkin Trans. 2 2000, 2001.
59. B. C. Gilbert, J. K. Stell, M. Jeff, J. Chem. Soc Perkin Trans. 2 1988, 1867.
60. A. de la Lande, H. Gérard, O. Parisel, Int. J. Quantum. Chem., DOI: 10.1002/qua.21679.
61. A. de la Lande. PhD thesis, University Paris 6, September, 2007.
62. This quantity is defined as the difference between the C-H and the O-H bond lengths.
63. S. M. Miller, J. P. Klinman, Biochemistry 1985, 24, 2114.
64. P. F. Fitzpatrick, D. R. Flory, Jr., J. J. Villafranca, Biochemistry 1985, 24, 2108.
65. J. P. Klinman, Chem. Rev. 1996, 96, 2541.
66. R. Kulathila, K. A. Merkler, D. J. Merkler, Nat. Prod. Rep. 1999, 16, 145.
67. W. A. Francisco, D. J. Merkler, N. J. Blackburn, J. P. Klinman, Biochemistry 1998, 37, 8244.
68. J. P. Evans, N. J. Blackburn, J. P. Klinman, Biochemistry 2006, 45, 15419.
69. M, see: A. de la Lande, S. Marti, O. Parisel, V. Moliner, J. Am. Chem. Soc. 2007, 129, 11 700.
70. J. P. Evans, K. Ahn, J. P. Klinman, J. Biol. Chem. 2003, 278, 49691.
71. J. P. Evans, K. Ahn, J. P. Klinman, J. Biol. Chem. 2004, 279, 5048.
72. A. T. Bauman, E. T. Yukl, K. Alkevich, A. L. McCormack, N. J. Blackburn, J. Biol. Chem. 2006, 281, 4190.