Reaction coordinate of a functional model of tyrosinase: Spectroscopic and computational characterization

Journal of the American Chemical Society

Volumn 131, Issue 18, 2009, Pages 6421-6438

  Holt, Bryan T Op't ^a   Vance, Michael A ^a   Mirica, Liviu M ^b   Heppner, David E ^a   Stack, T Daniel P ^a   Solomon, Edward I ^a  

^a STANFORD UNIVERSITY   (United States)

^b WASHINGTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC RINGS; AROMATIC SUBSTRATES; BRIDGING OXYGEN; C-O BOND FORMATION; CATECHOLATE; COPPER PROTEINS; CU COMPLEXES; DICOPPER; DIOXYGENS; ELECTROPHILIC AROMATIC SUBSTITUTIONS; ETHYLENE DIAMINE; FUNCTIONAL MODEL; ISOTOPIC LABELING; LOW TEMPERATURES; PROTONATION STATE; RATE-LIMITING STEPS; REACTION COORDINATES; RESONANCE RAMAN SPECTRA; SEMIQUINONES; SPECTROSCOPIC MODELS;

AROMATIC COMPOUNDS; LIGANDS; OXYGEN; RAMAN SPECTROSCOPY;

COPPER;

AROMATIC COMPOUND; CARBON; CATECHOL DERIVATIVE; COPPER COMPLEX; COPPER DERIVATIVE; ETHYLENEDIAMINE DERIVATIVE; MONOPHENOL MONOOXYGENASE; OXYGEN DERIVATIVE; PHENOL DERIVATIVE; PROTON; QUINONE DERIVATIVE; SEMIQUINONE; COPPER; DIAMINE; LIGAND; N,N'-BIS(DICHLOROACETYL)-1,8-OCTAMETHYLENEDIAMINE; ORGANOMETALLIC COMPOUND; OXYGEN;

ABSORPTION SPECTROSCOPY; ARTICLE; CHEMICAL BOND; CONTROLLED STUDY; DENSITY FUNCTIONAL THEORY; ELECTROPHILICITY; HYDROXYLATION; ISOTOPE LABELING; LOW TEMPERATURE; OXIDATION; PROTON TRANSPORT; RAMAN SPECTROMETRY; REDUCTION; SPECTROSCOPY; SUBSTITUTION REACTION; SYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY;

COPPER; DIAMINES; LIGANDS; MODELS, MOLECULAR; MONOPHENOL MONOOXYGENASE; ORGANOMETALLIC COMPOUNDS; OXYGEN; SPECTRUM ANALYSIS;

EID: 69949158121     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja807898h     Document Type: Article

References (79)

1. Solomon, E. I.; Sundaram, U. M.; Machonkin, T. E. Chem. Rev. 1996, 96, 2563-2605.
2. Klinman, J. P. Chem. Rev. 1996, 96, 2541-2562.
3. Solomon, E. I.; Baldwin, M. J.; Lowery, M. D. Chem. Rev. 1992, 92, 521-542.
4. Solomon, E. I.; Chen, P.; Metz, M.; Lee, S.-K.; Palmer, A. E. Angew. Chem., Int. Ed. 2001, 40, 4570-4590.
5. Eickman, N. C.; Solomon, E. I.; Larrabee, J. A.; Spiro, T. G.; Lerch, K. J. Am. Chem. Soc. 1978, 100, 6529-6531.
6. Hazes, B.; Magnus, K. A.; Bonaventura, C.; Bonaventura, J.; Dauter, Z.; Kalk, K. H.; Hol, W. G. Protein Sci. 1993, 2, 597-619.
7. Klabunde, T.; Eicken, C.; Sacchettin, J. C.; Krebs, B. Nat. Struct. Biol. 1998, 5, 1084-1090.
8. Matoba, Y.; Kumagai, T.; Yamamoto, A.; Yoshitsu, H.; Sugiyama, M. J. Biol. Chem. 2006, 281, 8981-8990.
9. Wilcox, D. E.; Porras, A. G.; Hwang, Y. T.; Lerch, K.; Winkler, M. E.; Solomon, E. I. J. Am. Chem. Soc. 1985, 107, 4015-4027.
10. Winkler, M. E.; Lerch, K.; Solomon, E. I. J. Am. Chem. Soc. 1981, 103, 7003-7005.
11. Mirica, L. M.; Ottenwaelder, X.; Stack, T. D. P. Chem. Rev. 2004, 104, 1013-1045.
12. Lewis, E. A.; Tolman, W. B. Chem. Rev. 2004, 104, 1047-1076.
13. Cruse, R. W.; Kaderli, S.; Meyer, C. J.; Zuberbühler, A. D.; Karlin, K. D. J. Am. Chem. Soc. 1988, 110, 5020-5024.
14. Mirica, L. M.; Vance, M.; Rudd, D. J.; Hedman, B.; Hodgson, K. O.; Solomon, E. I.; Stack, T. D. P. J. Am. Chem. Soc. 2002, 124, 9332-9333.
15. Mirica, L. M.; Vance, M.; Rudd, D. J.; Hedman, B.; Hodgson, K. O.; Solomon, E. I.; Stack, T. D. P. Science 2005, 308, 1890-1892.
16. Mirica, L. M.; Vance, M.; Rudd, D. J.; Hedman, B.; Hodgson, K. O.; Solomon, E. I.; Stack, T. D. P. J. Am. Chem. Soc. 2006, 128, 2654-2665.
17. Pidcock, E.; Obias, H. V.; Zhang, C. X.; Karlin, K. D.; Solomon, E. I. J. Am. Chem. Soc. 1998, 120, 7841-7847.
18. Itoh, S.; Kumei, H.; Taki, M.; Nagatomo, S.; Kitagawa, T.; Fukuzumi, S. J. Am. Chem. Soc. 2001, 123, 6708-6709.
19. Palavincini, S.; Granata, A.; Monzani, E.; Casella, L. J. Am. Chem. Soc. 2005, 127, 18031-18036.
20. Santagostini, L.; Gullotti, M.; Monzani, E.; Casella, L.; Dillinger, R.; Tuczek, F. Chem. Eur. J. 2000, 6, 519-522.
21. Karlin, K. D.; Haka, M. S.; Cruse, R. W.; Meyer, G. J.; Farooq, A.; Gultneh, Y.; Hayes, J. C.; Zubieta, J. J. Am. Chem. Soc. 1988, 110, 1196-1207.
22. Obias, H. V.; Lin, Y.; Murthy, N. N.; Pidcock, E.; Solomon, E. I.; Ralle, M.; Blackburn, N. J.; Neuhold, Y.-M.; Zuberbühler, A. D.; Karlin, K. D. J. Am. Chem. Soc. 1998, 120, 12960-12961.
23. Kitajima, N.; Fujisawa, K.; Morooka, T.; Toriumi, K. J. Am. Chem. Soc. 1989, 111, 8975-8976.
24. Karlin, K. D.; Hayes, J. C.; Gultneh, Y.; Cruse, R. W.; McKown, J. W.; Hutchison, J. P.; Zubieta, J. J. Am. Chem. Soc. 1984, 106, 2121-2128.
25. Murthy, N. N.; Mahroof-Tahir, M.; Karlin, K. D. Inorg. Chem. 2001, 40, 628-635.
26. Karlin, K. D.; TyeklàFarooq, A.; Haka, M. S.; Ghosh, P.; Cruse, R. W.; Gultneh, Y.; Hayes, J. C.; Toscano, P. J.; Zubieta, J. Inorg. Chem. 1992, 31, 1436-1451.
27. Halfen, J. A.; Mahapatra, S.; Wilkinson, E. C.; Kaderli, S.; Young, V. G.; Cramer, C. J.; Que, L., Jr.; Tolman, W. B. Science 1996, 271, 1397-1400.
28. Cole, A. P.; Mahadevan, V.; Mirica, L. M.; Ottenwaelder, X.; Stack, T. D. P. Inorg. Chem. 2005, 44, 7345-7364.
29. Mahadevan, V.; DuBois, J. L.; Hedman, B.; Hodgson, K. O.; Stack, T. D. P. J. Am. Chem. Soc. 1999, 121, 5583-5584.
30. Mahadevan, V.; Hou, Z. G.; Cole, A. P.; Root, D. E.; Lal, T. K.; Solomon, E. I.; Stack, T. D. P. J. Am. Chem. Soc. 1997, 119, 11996-11997.
31. Stack, T. D. P. Dalton Trans. 2003, 10, 1881-1889.
32. Cahoy, J.; Holland, P. L.; Tolman, W. B. Inorg. Chem. 1999, 38, 2161-2168.
33. Mahadevan, V.; Henson, M. J.; Solomon, E. I.; Stack, T. D. P. J. Am. Chem. Soc. 2000, 122, 10249-10250.
34. Eickman, N. C.; Himmelwright, R. S.; Solomon, E. I. Proc. Natl. Acad. Sci. 1979, 76, 2094-2098.
35. Baldwin, M. J.; Root, D. E.; Pate, J. E.; Fujisawa, K.; Kitajima, N.; Solomon, E. I. J. Am. Chem. Soc. 1992, 114, 10421.
36. Henson, M. J.; Vance, M.; Zhang, C. X.; Liang, H. C.; Karlin, K. D.; Solomon, E. I. J. Am. Chem. Soc. 2003, 125, 5186-5192.
37. Liang, H.; Zhang, C. X.; Henson, M. J.; Sommer, R. D.; Hatwell, K. R.; Kaderli, S.; Zuberbühler, A. D.; Rheingold, A. L.; Solomon, E. I.; Karlin, K. D. J. Am. Chem. Soc. 2001, 124, 4170-4171.
38. Pau, M. Y. M.; Davis, M. I.; Orville, A. M.; Lipscomb, J. D.; Solomon, E. I. J. Am. Chem. Soc. 2007, 129, 1944-1958.
39. Schenk, G.; Pau, M. Y. M.; Solomon, E. I. J. Am. Chem. Soc. 2004, 126, 505-515.
40. Szilagyi, R. K.; Metz, M.; Solomon, E. I. J. Phys. Chem. A 2002, 106, 2994-3007.
41. Henson, M. J.; Mukherjee, P.; Root, D. E.; Stack, T. D. P.; Solomon, E. I. J. Am. Chem. Soc. s1999, 121, 10332-10345.
42. Casella, L.; Monzani, E.; Gullotti, M.; Caragnino, D.; Cerina, G.; Santagostini, L.; Ugo, R. Inorg. Chem. 1996, 35, 7516-7525.
43. Reim, J.; Krebs, B. J. Chem. Soc., Dalton Trans. 1997, 3793-3804.
44. Lynch, M. W.; Valentine, M.; Hendrickson, D. N. J. Am. Chem. Soc. 1982, 104, 6982-6989.
45. Strufkens, D. J.; Snoeck, T. L.; Lever, A. B. P. Inorg. Chem. 1988, 27, 953-956.
46. Gordon, D. J.; Fenske, R. F. Inorg. Chem. 1982, 8, 2907-2915.
47. Streitwieser, A., Jr.; Jagow, R. H.; Fahey, R. C.; Suzuki, S. J. Am. Chem. Soc. 1958, 80, 2326-2332.
48. Mireia, G.; Luis, J. M.; Solá, M.; Siegbahn, P. E. M. J. Biol. Inorg. Chem. 2008, 14, 229-242.
49. Becker, M.; Schindler, S.; Karlin, K. D.; Kaden, T. A.; Kaderli, S.; Palanché, T.; Zuberbühler, A. D. Inorg. Chem. 1999, 38, 1989-1995.
50. Cruse, R. W.; Kaderli, S.; Karlin, K. D.; Zuberbühler, A. D. J. Am. Chem. Soc. 1988, 110, 6882-6883.
51. Karlin, K. D.; Nasir, M. S.; Cohen, B. I.; Cruse, R. W.; Kaderli, S.; Zuberbühler, A. D. J. Am. Chem. Soc. 1994, 116, 1324-1336.
52. Suzuki, K.; Shimokawa, C.; Morioka, C.; Itoh, S. Biochem. 2008, 47, 7108-7115.
53. Morioka, C.; Tachi, Y.; Suzuki, S.; Itoh, S. J. Am. Chem. Soc. 2006, 128, 6788-6789.
54. Matoba, Y.; Kumagai, T.; Yamamoto, A.; Yoshitsu, H.; Sugiyama, M. J. Biol. Chem. 2006, 281, 8981-8990.
55. Op't Holt, B. T.; Dustman, J.; Solomon, E. I. ChemTracts Inorg. Chem. 2006, 19, 435-444.
56. Kubas, G. J.; Monzyk, B.; Crumbliss, A. L. Inorg. Synth. 1979, 19, 90-92.
57. Mandal, S.; Macikenas, D.; Protasiewicz, J. D.; Sayre, L. M. J. Org. Chem. 2000, 65, 4804-4809.
58. Frisch, M. J.; et al. Gaussian03, ReVision D.01 or E.01; Gaussian, Inc.: Wallingford, CT, 2004.
59. Schaefer, A.; Horn, H.; Alrichs, R. J. Chem. Phys. 1992, 97, 2571-2577.
60. Schaefer, A.; Huber, C.; Alrichs, R. J. Chem. Phys. 1994, 100, 5289-5835.
61. Binkley, J. S.; Pople, J. A.; Hehre, W. J. J. Am. Chem. Soc. 1980, 102, 939-947.
62. Gordon, M. S.; Binkley, J. S.; Pople, J. A.; Pietro, W. J.; Hehre, W. J. J. Am. Chem. Soc. 1982, 104, 2797-2803.
63. Pietro, W. J.; Francl, M. M.; Hehre, W. J.; Defrees, D. J.; Pople, J. A.; Binkley, J. S. J. Am. Chem. Soc. 1982, 104, 5039-5048.
64. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
65. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
66. Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Chem. Phys. Lett. 1989, 157, 200-206.
67. Schlegel, H. B. J. Comput. Chem. 1982, 3, 214-218.
68. Yamaguchi, K.; Jensen, F.; Dorigo, A.; Houk, K. N. Chem. Phys. Lett. 1988, 149, 537-542.
69. Bauernschmitt, R.; Alrichs, R. Chem. Phys. Lett. 1996, 256, 454-464.
70. Casida, M. E.; Jamorski, C.; Casida, K. C.; Salahub, D. R. J. Chem. Phys. 1998, 108, 4439-4449.
71. Stratmann, R. E.; Scuseria, G. E.; Frisch, M. J. J. Chem. Phys. 1998, 109, 8218-8224.
72. Gorelesky, S. I. SWizard, reVision 4.4; University of Ottawa: Ottawa, Canada, 2008.
73. Carpenter, J. E.; Weinhold, F. J. Mol. Struct. (Theochem) 1988, 46, 41-62.
74. Foster, J. P.; Weinhold, F. J. Am. Chem. Soc. 1980, 102, 7211-7218.
75. Tenderholt, A. L. QMForge, Version 2.1; Stanford University: Stanford, CA, 2008.
76. Humphrey, W.; Dalke, A.; Schulten, K. J. Mol. Graphics 1996, 14, 33-38.
77. Stone, J. Tachyon ray tracer, Version 0.97; University of Illinois at Urbana-Champaign: Urbana, IL, 2007.
78. Dennington, I. R.; Todd, K.; Millam, J. M. ; Eppinnett, K. ; Hovell, W. L.; Gilliland, R. GaussView, Version 3.09; Semichem, Inc.: Shawnee Mission, KS, 2003.
79. Schaftenaar, G.; Noordik, J. H. J. Comput.-Aided Mol. Des. 2000, 14, 123-134.