Models of high-valent heme protein intermediates: A quantum chemical study of iron(IV) porphyrins with two univalent axial π-bonding ligands

Journal of Physical Chemistry B

Volumn 108, Issue 1, 2004, Pages 452-456

  Conradie, Jeanet ^a,b   Swarts, Jannie C ^b   Ghosh, Abhik ^a  

^a UNIVERSITY OF TROMSØ   (Norway)

^b UNIVERSITY OF THE FREE STATE   (South Africa)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCHEMISTRY; CHEMICAL BONDS; ELECTRONIC DENSITY OF STATES; IRON COMPOUNDS; MANGANESE COMPOUNDS; QUANTUM THEORY; SPECTROSCOPIC ANALYSIS; TRANSITION METALS;

CYTOCHROMES; ELECTRONIC SPIN DENSITY; HEME PROTEIN; IRON PORPHYRINS; MANGANESE PORPHYRINS; QUANTUM CHEMICAL STUDY;

PROTEINS;

EID: 1642460760     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp030817p     Document Type: Article

References (59)

1. Dawson, J. H.; Sono, M. Chem. Rev. 1987, 87, 1255.
2. Que, L., Jr.; Tolman, W. B. Angew. Chem., Int. Ed. 2002, 41, 1114.
3. Terner, J.; Gold, A.; Weiss, R.; Mandon, D.; Trautwein, A. X. J. Porphyrins Phthalocyanines 2001, 5, 357.
4. Que, L., Jr. In Bioinorganic Catalysis, 2nd ed.; Reedijk, J., Bouwman, E., Eds.; Marcel Dekker: New York, 1999, 269.
5. Solomon, E. I.; Brunold, T. C.; Davis, M. I.; Kemsley, J. N.; Lee, S.-K.; Lehnert, N.; Neese, F.; Skulan, A. J.; Yang, Y.-S.; Zhou, J. Chem. Rev. 2000, 100, 235.
6. Grapperhaus, C. A.; Mienert, B.; Bill, E.; Weyhermüller, T.; Wieghardt, K. Inorg. Chem. 2000, 39, 5306.
7. Kim, M. H.; Rohde, J.-U.; Stubna, A.; Bukowski, M. R.; Costas, M.; Ho, R. Y. N.; Münck, E.; Nam, W.; Que, L., Jr. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 3665.
8. Rohde, J.-U.; In, J. H.; Lim, M. H.; Brennessel, W. W.; Bukowski, M. R.; Stubna, A.; Münck, E.; Nam, W.; Que, L., Jr. Science 2003, 299, 1037.
9. For a broad quantum chemical survey of high-valent metalloporphyrins, see: Ghosh, A.; Steene, E. J. Biol. Inorg. Chem. 2001, 6, 739.
10. Siegbahn, P. E. M.; Blomberg, M. R. A. Chem. Rev. 2000, 100, 421.
11. Guallar, V.; Gherman, B. F.; Lippard, S. J.; Friesner, R. A. Curr. Opin. Chem. Biol. 2002, 6, 236.
12. For a critical discussion of the limitations of DFT vis-à-vis transition metal calculations, see: Ghosh, A.; Taylor, P. R. Curr. Opin. Chem. Biol. 2003, 7, 113.
13. Groves, J. T.; Quinn, R.; McMurry, T. J.; Nakamura, M.; Lang, G.; Boso, B. J. Am. Chem. Soc. 1985, 107, 354.
14. Calderwood, T. S.; Lee, W. A.; Bruice, T. C. J. Am. Chem. Soc. 1985, 107, 8272.
15. Lee, W. A.; Calderwood, T. S.; Bruice, T. C. Proc. Natl. Acad. Sci. U.S.A. 1985, 82, 4301.
16. Swistak, C.; X. H. Mu, Kadish, K. M. Inorg. Chem. 1987, 26, 4360.
17. Filatov, M.; Harris, N.; Shaik, S. Angew. Chem., Int. Ed. 1999, 38, 3510.
18. Kamachi, T.; Yoshizawa, K. J. Am. Chem. Soc. 2003, 125, 4652.
19. Groves, J. T. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 3569.
20. Shaik, S.; de Visser, S. P.; Ogliaro, F.; Schwarz, H.; Schröder, D. Curr. Opin. Chem. Biol. 2002, 6, 556.
21. de Visser, S. P.; Ogliaro, F.; Harris, N.; Shaik, S. J. Am. Chem. Soc. 2001, 123, 3037.
22. Penner-Hahn, J.; Eble, K. S.; McMurry, T. J.; Renner, M.; Balch, A. L.; Groves, J. T.; Dawson, J. H.; Hodgson, K. O. J. Am. Chem. Soc. 1986, 108, 7819.
23. Berglund, G. I.; Carlsson, G. H.; Smith, A. T.; Szöke, H.; Henriksen, A.; Hajdu, J. Nature 2002, 417, 463.
24. Sitter, A. J.; Reczek, C. M.; Terner, J. J. Biol. Chem. 1985, 260, 7515.
25. Schappacher, M.; Chottard, G.; Weiss, R. J. Chem. Soc., Chem. Commun. 1986, 93.
26. Egawa, T.; Proshlyakov, H.; Miki, R.; Makino, T.; Ogura, T.; Kitagawa, T.; Ishimura, Y. J. Biol. Inorg. Chem. 2001, 6, 46.
27. Hosten, C. M.; Sullivan, A. M.; Palaniappan, V.; Fitzgerald, M. M.; Terner, J. J. Biol. Chem. 1994, 269, 13966.
28. Ghosh, A.; Steene, E. J. Inorg. Biochem. 2002, 91, 423.
29. Ghosh, A.; Persson, B. J.; Taylor, P. R. J. Biol. Inorg. Chem. 2003, 5, 345.
30. Vangberg, T.; Lie, R.; Ghosh, A. J. Am. Chem. Soc. 2002, 124, 8122-8130.
31. For the first DFT calculations on Fe(IV)-oxo porphyrins, see: Ghosh, A.; Almol̈f, J.; Que, L., Jr. J. Phys. Chem. 1994, 98, 5576.
32. Deeth, R. J. J. Am. Chem. Soc. 1999, 121, 6074.
33. Vangberg, T.; Ghosh, A. J. Am. Chem. Soc. 1999, 121, 12154.
34. Harris, D. L. Curr. Opin. Chem. Biol. 2001, 5, 724.
35. Kuramochi, H.; Noodleman, L.; Case, D. A J. Am. Chem. Soc. 1997, 119, 11442.
36. Green, M. T. J. Am. Chem. Soc. 1998, 120, 10772.
37. Green, M. T. J. Am. Chem. Soc. 1999, 121, 7939.
38. Green, M. T. J. Am. Chem. Soc. 2001, 123, 9218.
39. Ghosh, A.; Gonzalez, E.; Vangberg, T.; Taylor, J. Porphyrin Phthalocyanines 2001, 5, 345.
40. Dey, A.; Ghosh, A. J. Am. Chem. Soc. 2002, 124, 3206.
41. Ghosh, A.; Gonzalez, E. Isr. J. Chem. 2000, 40, 1.
42. For our latest study on high-valent Fe and Cu corroles, see: Steene, E.; Day, A.; Ghosh, A. J. Am. Chem. Soc., in press.
43. Steene, E.; Wondimagegn, T.; Ghosh, A. J. Phys. Chem. B 2001, 105, 11406. Addition/Correction: J. Phys. Chem. B. 2002, 106, 4312.
44. Tangen, E.; Ghosh, A. J. Am. Chem. Soc. 2002, 124, 8117.
45. Zakharieva, O.; Schunemann, V.; Gerdan, M.; Licoccia, S.; Cai, S.; Walker, F. A.; Trautwein, A. X. J. Am. Chem. Soc. 2002, 124, 6636.
46. Ghosh, A.; Wondimagegn, T.; Gonzalez, E.; Halvorsen, I. J. Inorg. Biochem. 2000, 78, 79.
47. Wondimagegn, T.; Ghosh, A. J. Am. Chem. Soc. 2001, 123, 1543.
48. Ghosh, A.; Wondimagegn, T.; Parusel, A. B. J. J. Am. Chem. Soc. 2000, 122, 5100.
49. For the first DFT study of a high-valent iron diamond-core intermediate, see: Ghosh, A.; Almlof, J.; Que, L. Angew. Chem., Int. Ed. Engl. 1996, 35, 770.
50. For a follow-up study, see: Ghosh, A.; Tangen, E.; Gonzalez, E.; Que, L., Jr. Angew. Chem. Int. Ed., in press.
51. For a thorough experimental study of the electronic structure of Mn(IV) complexes, see: Kaustov, L.; Tal, M. E.; Shames, A. I.; Gross, Z. Inorg. Chem. 1997, 36, 3503.
52. All calculations were carried out with the ADF program system, the VWN local exchange-correlation functional, PW91 gradient corrections, Slater-type triple-ζ plus polarization (TZP) basis sets, a fine mesh for numerical integration of matrix elements, and tight criteria for geometry optimizations. For additional technical details, the reader is referred to the program, available from: Scientific Computing and Modeling, Department of Theoretical Chemistry, Vrije Universiteit, 1081 HV Amsterdam, The Netherlands.
53. Eikey, R. A.; Khan, S. I.; Abu-Omar, M. Angew. Chem., Int. Ed. 2002, 41, 3591.
54. Czernuszewicz, R. S.; Su, Y. S.; Stern, M. K.; Macor, K. A.; Kim, D.; Groves, J. T.; Spiro, T. G. J. Am. Chem. Soc. 1988, 110, 4158.
55. This is indeed what is expected. Dinitrosylheme intermediates are a suprising violation of this scenario; they strongly favor a cisoid orientation of the NO ligands: Conradie, J.; Wondimagegn, T.; Ghosh, A. J. Am. Chem. Soc. 2003, 125, 4968.
56. 2 exhibits significant paramagnetic shifts for the β-protons. However, as in the case Fe(porphyrinato)Cl complexes, we believe that these paramagnetic shifts result from very small unpaired spin populations at the β-carbons.
57. 2+ intermediates relative to that given in the original study, ref 57: Gans, P.; Buisson, G.; Duée, E.; Marchon, J. C.; Erler, B. S.; Scholz, W. F.; Reed, C. A. J. Am. Chem. Soc. 1986, 108, 1223.
58. Goff, H. M.; Phillippi, M. J. Am. Chem. Soc. 1983, 105, 7567.
59. Conradie, J.; Ghosh, A. J. Phys. Chem. B 2003, 107, 6486.