Functional Models for Catechol 1,2-Dioxygenase. Synthesis, Structure, Spectra, and Catalytic Activity of Certain Tripodal Iron(III) Complexes

Inorganic Chemistry

Volumn 37, Issue 12, 1998, Pages 2943-2951

  Viswanathan, Rathinam ^a   Palaniandavar, Mallayan ^a   Balasubramanian, Thailampillai ^a   Muthiah, Thomas P ^a  

^a BHARATHIDASAN UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000093758     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic970708n     Document Type: Article

References (71)

1. Microbial Degradation of Organic Molecules; Gibson, D. T., Ed.; Marcel Dekker: New York, 1984; p 535.
2. Feig, A. L.; Lippard, S. J. Chem. Rev. 1994, 94, 759.
3. Que, L., Jr.; Ho, R. Y. N. Chem. Rev. 1996, 96, 2607.
4. Lipscomb, J. D.; Orville, A. M. In Metal Ions in Biological Systems; Sigel, H., Sigel, A., Eds.; Marcel Dekker: New York, 1993; p 243.
5. (a) Ohlendorf, D. H.; Lipscomb, J. D.; Weber, P. C. Nature 1988, 336, 403.
6. (b) Ohlendorf, D. H.; Orville, A. M.; Lipscomb, J. D. J. Mol. Biol. 1994, 244, 586.
7. (a) Que, L., Jr.; Lipscomb, J. D.; Zimmermann, R.; Munck, E.; Orme Johnson, W. H.; Orme-Johnson, N. R. Biochim. Biophys. Acta 1976, 452, 320.
8. (b) Whittaker, J. W.; Lipscomb, J. D.; Kent, T. A.; Munck, E. J. Biol. Chem. 1984, 259, 4466.
9. Kent, T. A.; Munck, E.; Pyrz, J. W.; Widom, J.; Que, L., Jr. Inorg. Chem. 1987, 26, 1402.
10. Que, L., Jr.; Heistand, R. H., II. J. Am. Chem. Soc. 1979, 101, 2219.
11. Heistand, R. H., II; Lauffer, R. B.; Fikrig, E.; Que, L., Jr. J. Am. Chem. Soc. 1982, 104, 2789.
12. Cox, D. D.; Que, L., Jr. J. Am. Chem. Soc. 1988, 110, 8085.
13. Que, L., Jr.; Kolanczyk, R. C.; White, L. S. J. Am. Chem. Soc. 1987, 109, 5373.
14. Cox, D. D.; Benkovic, S. J.; Bloom, L. M.; Bradley, F. C.; Nelson, M. J.; Que, L., Jr.; Wallick, D. E. J. Am. Chem. Soc. 1988, 104, 2026.
15. 2. Kim, C.; Chen, K.; Kim, J.; Que, L., Jr. J. Am. Chem. Soc. 1997, 119, 5964.
16. Que, L., Jr.; Lipscomb, J. D.; Munck, E.; Wood, J. M. Biochim. Biophys. Acta 1977, 485, 60.
17. Que, L., Jr.; Lauffer, R. B.; Lynch, J. B.; Murch, B. P.; Pyrz, J. W. J. Am. Chem. Soc. 1987, 109, 5381.
18. II for activity, have been very recently proposed to utilize an oxygen activation mechanism in which nucleophilic Superoxide attacks the bound substrate. Ito, M.; Que, L., Jr. Angew. Chem., Int. Ed. Engl. 1997, 36, 1342.
19. Support for the alkylperoxo - iron(III) species has been obtained. Bianchini, C.; Frediani, P.; Laschi, F.; Meli, A.; Vizza, F.; Zanello, P. Inorg. Chem. 1990, 29, 3402. Barbaro, P.; Bianchini, C.; Linn, K.; Mealli, C.; Meli, A.; Vizza, F.; Laschi, F.; Zanello, P. Inorg. Chim. Acta 1992, 198-200, 31. Barbara, P.; Bianchini, C.; Mealli, C.; Meli, A. J. Am. Chem. Soc. 1991, 113, 3181. Such alkylperoxo species have been invoked in the mechanism of alkane functionalization catalyzed by non-heme iron complexes in concert with alkyl hydroperoxides. Kim, J.; Larka, E.; Wilkinson, E. C.; Que, L., Jr. Angew. Chem., Int. Ed. Engl. 1995, 34, 2048.
20. Support for the alkylperoxo - iron(III) species has been obtained. Bianchini, C.; Frediani, P.; Laschi, F.; Meli, A.; Vizza, F.; Zanello, P. Inorg. Chem. 1990, 29, 3402. Barbaro, P.; Bianchini, C.; Linn, K.; Mealli, C.; Meli, A.; Vizza, F.; Laschi, F.; Zanello, P. Inorg. Chim. Acta 1992, 198-200, 31. Barbara, P.; Bianchini, C.; Mealli, C.; Meli, A. J. Am. Chem. Soc. 1991, 113, 3181. Such alkylperoxo species have been invoked in the mechanism of alkane functionalization catalyzed by non-heme iron complexes in concert with alkyl hydroperoxides. Kim, J.; Larka, E.; Wilkinson, E. C.; Que, L., Jr. Angew. Chem., Int. Ed. Engl. 1995, 34, 2048.
21. Support for the alkylperoxo - iron(III) species has been obtained. Bianchini, C.; Frediani, P.; Laschi, F.; Meli, A.; Vizza, F.; Zanello, P. Inorg. Chem. 1990, 29, 3402. Barbaro, P.; Bianchini, C.; Linn, K.; Mealli, C.; Meli, A.; Vizza, F.; Laschi, F.; Zanello, P. Inorg. Chim. Acta 1992, 198-200, 31. Barbara, P.; Bianchini, C.; Mealli, C.; Meli, A. J. Am. Chem. Soc. 1991, 113, 3181. Such alkylperoxo species have been invoked in the mechanism of alkane functionalization catalyzed by non-heme iron complexes in concert with alkyl hydroperoxides. Kim, J.; Larka, E.; Wilkinson, E. C.; Que, L., Jr. Angew. Chem., Int. Ed. Engl. 1995, 34, 2048.
22. Support for the alkylperoxo - iron(III) species has been obtained. Bianchini, C.; Frediani, P.; Laschi, F.; Meli, A.; Vizza, F.; Zanello, P. Inorg. Chem. 1990, 29, 3402. Barbaro, P.; Bianchini, C.; Linn, K.; Mealli, C.; Meli, A.; Vizza, F.; Laschi, F.; Zanello, P. Inorg. Chim. Acta 1992, 198-200, 31. Barbara, P.; Bianchini, C.; Mealli, C.; Meli, A. J. Am. Chem. Soc. 1991, 113, 3181. Such alkylperoxo species have been invoked in the mechanism of alkane functionalization catalyzed by non-heme iron complexes in concert with alkyl hydroperoxides. Kim, J.; Larka, E.; Wilkinson, E. C.; Que, L., Jr. Angew. Chem., Int. Ed. Engl. 1995, 34, 2048.
23. Nishida, Y.; Shimo, H.; Kida, S. J. Chem. Soc., Chem. Commun. 1984, 1611.
24. Duda, M.; Pascaly, M.; Krebs, B. J. Chem. Soc., Chem. Commun. 1997, 835.
25. Que, L., Jr.; Heistand, R. H., II; Mayer, R.; Roe, A. L. Biochemistry 1980, 19, 2588.
26. Que, L., Jr.; Epstein, R. M. Biochemistry 1981, 20, 2545.
27. Siu, C.-T.; Orville, A. M.; Lipscomb, J. D.; Ohlendorf, D. H.; Que, L., Jr. Biochemistry 1992, 31, 10443.
28. Felton, R. H.; Barrow, W. L.; May, S. W.; Sowell, A. L.; Goel, S. Bunker, G.; Stern, E. A. J. Am. Chem. Soc. 1982, 104, 6132.
29. Whittaker, J. W.; Lipscomb, J. D., J. Biol. Chem. 1984, 259, 4487.
30. True, A. E.; Orville, A. M.; Pearce, L. L.; Lipscomb, J. D.; Que, L., Jr. Biochemistry 1990, 29, 10847.
31. (a) Walsh, T. A.; Ballou, D. P.; Mayer, R.; Que, L., Jr. J. Biol. Chem. 1983, 258, 14422.
32. (b) Roe, A. L.; Schneider, D. J.; Mayer, R. J.; Pyrz, J. W.; Widom, J.; Que, L., Jr. J. Am. Chem. Soc. 1984, 106, 1676.
33. (a) Koch, W. O.; Kruger, H.-J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2928.
34. (b) Koch, W. O.; Kruger, H.-J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2671.
35. Aminabhavi, T. M.; Biradar, N. S.; Patil, S. B. Inorg. Chim. Acta 1986, 125, 125.
36. Horning, E. C., Ed. Organic Syntheses; Wiley: New York, 1955; Collect. Vol. III, p 468.
37. Karlin, K. D.; Hayes, J. C.; Juen, S.; Hutchinson, J.; P. Zubieta, J. Inorg. Chem. 1982, 21, 4106.
38. Usha, S.; Pandiyan, T.; Palaniandavar, M. Indian J. Chem. 1992, 55, 878.
39. Thompson, L. K.; Ramaswamy, B. S.; Seymour, E. A. Can. J. Chem. 1977, 55, 878.
40. SHELX-86: Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467.
41. SHELXL-93: Sheldrick, G. M. SHELXL-93; University of Gottingen: Gottingen, Germany, 1993.
42. PARST, A System of Computer Routines for Calculation of Molecular Parameters from Results of Crystal Structure Analysis: Nordelli, M. Comput. Chem. 1983, 7, 95.
43. Demmin, T. R.; Rogic, M. M. J. Org. Chem. 1980, 45, 4072.
44. 2]Cl crystallized in the triclinic space group with a = 8.404(7) Å, b = 9.897(11) Å, and c = 15.006(10) Å; α = 86.73(9)°, β = 86.95(7)°, and γ = 80.39(9)°. The structure has been determined, and a tertiary amine, three benzimidazole nitrogens, and two chloride ions are coordinated to iron(III) in a distorted octahedral structure. The refinement of the crystal structure is in progress, and the complete details will be published elsewhere.
45. Schakal: A Fortran program for plotting crystal structures, Germany, 1992.
46. Ainscough, E. W.; Brodie, A. M.; Plowman, J. E.; Brown, K. L.; Addison, A. W.; Gainsford, A. R. Inorg. Chem. 1980, 19, 3655.
47. Lauffer, R. B.; Heistand, R. H., II; Que, L., Jr. Inorg. Chem. 1983, 22, 50.
48. Malfant, I.; Morgenstern-Badrau, I.; Philoche-Lavisalles, M.; Lloret, F. J. Chem. Soc., Chem. Commun. 1990, 1338.
49. McDevitt, M. R.; Addison, A. W.; Sinn, E.; Thompson, L. K. Inorg. Chem. 1990, 29, 3425.
50. Okamoto, K.-I.; Kanamori, K.; Hidaka, J. Acta Crystallogr. 1990, C46, 1640.
51. Yan, S.; Que, L., Jr.; Taylor, L. F.; Anderson, O. P. J. Am. Chem. Soc. 1988, 110, 5222.
52. Jang, H. G.; Cox, D. D.; Que, L., Jr. J. Am. Chem. Soc. 1991, 113, 9200.
53. Uma, R.; Viswanathan, R.; Palaniandavar, M.; Lakshmi Narayanan, M.; Manohar, H. J. Chem. Soc., Dalton. Trans. 1994, 1219.
54. Raymond, K. N.; Isied, S. S.; Brown, L. D.; Fronczek, F. R.; Nibert, J. H. J. Am. Chem. Soc. 1976, 98, 1767.
55. Clarke, E. T.; Martell, A. E.; Reibenspies, J. Inorg. Chim. Acta 1992, 196, 177.
56. (a) Whittaker, J. W.; Lipscomb, J. D. J. Biol. Chem. 1984, 259, 4487.
57. (b) Orville, A. M.; Lipscomb, J. D. J. Biol. Chem. 1989, 264, 8791.
58. Casella, L.; Gullotti, M.; Pintar, A.; Messouri, L.; Rockenbauer, A.; Gyor, M. Inorg. Chem. 1987, 26, 1031.
59. Pyrz, J. W.; Roe, A. L.; Stern, L. J.; Que, L., Jr. J. Am. Chem. Soc. 1985, 107, 614.
60. The presence of two histidine residues at the sites of PAH has been recently suggested on the basis of mutagenesis studies, with carboxylate oxygen and a solvent oxygen completing the coordination sphere. Gibbs, B. S.; Wojchowski, D.; Benkovic, S. J. J. Biol. Chem. 1993, 268, 8046.
61. Loeb, K. E.; Westre, T. E.; Kappock, T. J.; Mitic, N.; Glasfeld, E.; Caradonna, J. P.; Hedmann, B.; Hodgson, K. O.; Solomon, E. I. J. Am. Chem. Soc. 1977, 119, 1901.
62. (a) Viswanathan, R.; Palaniandavar, M. J. Chem. Soc., Dalton Trans. 1995, 1259.
63. (b) Palaniandavar, M.; Viswanathan, R. Proc. Indian Acad. Sci., Chem. Sci. 1996, 108, 235.
64. Johnson, C. R.; Henderson, W. W.; Shepherd, R. F. Inorg. Chem. 1984, 23, 2754.
65. Nanni, E. J.; Stallings, M. D.; Sawyer, D. T. J. Am. Chem. Soc. 1980, 102, 4481.
66. Lauffer, R. B.; Heistand, R. H., II; Que, L., Jr. J. Am. Chem. Soc. 1981, 103, 3947.
67. White, L. S.; Nilsson, L. H.; Pignolet, L. H.; Que, L., Jr. J. Am. Chem. Soc. 1984, 106, 8312.
68. 17
69. Felton, R. H.; Cheung, L. D.; Philips, R. S.; May, S. W. Biochem. Biophys. Res. Commun. 1978, 85, 844.
70. Que, L. Jr.; Lipscomb, J. D.; Zimmermann, R.; Munck, E.; Orme-Johnson, N. R.; Orme-Johnson, W. H. Biochim. Biophys. Acta 1976, 452, 320.
71. Kim, J.; Harrison, R. G.; Kim, C.; Que, L., Jr. J. Am. Chem. Soc. 1996, 118, 4373.