A synthetic model of the putative Fe(II)-iminobenzosemiquinonate intermediate in the catalytic cycle of o-aminophenol dioxygenases

Journal of the American Chemical Society

Volumn 134, Issue 12, 2012, Pages 5460-5463

  Bittner, Michael M ^a   Lindeman, Sergey V ^a   Fiedler, Adam T ^a  

^a Marquette University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC SUBSTRATES; CATALYTIC CYCLES; COMPUTATIONAL ANALYSIS; DIOXYGENASES; NONHEME; RING CLEAVAGE; SYNTHETIC MODELS;

ELECTRONIC STRUCTURE; IRON COMPOUNDS;

SUBSTRATES;

AMINOPHENOL; DIOXYGENASE; IMINOBENZOSEMIQUINONATE; IRON DERIVATIVE; RADICAL; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL MODEL; CHEMICAL STRUCTURE; ELECTRON; MATHEMATICAL ANALYSIS; OXIDATION; RING OPENING; SPECTROSCOPY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

AMINOPHENOLS; BENZOQUINONES; BIOMIMETIC MATERIALS; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; DIOXYGENASES; ELECTRONS; FERROUS COMPOUNDS; MODELS, MOLECULAR; OXIDATION-REDUCTION; SPECTRUM ANALYSIS;

EID: 84859121859     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja212163t     Document Type: Article

References (29)

1. Costas, M.; Mehn, M. P.; Jensen, M. P.; Que, L., Jr. Chem. Rev. 2004, 104, 939-986
2. Vaillancourt, F. H.; Bolin, J. T.; Eltis, L. D. Crit. Rev. Biochem. Mol. 2006, 41, 241-267
3. Lipscomb, J. D. Curr. Opin. Struct. Biol. 2008, 18, 644-649
4. Li, X. W.; Guo, M.; Fan, J.; Tang, W. Y.; Wang, D. Q.; Ge, H. H.; Rong, H.; Teng, M. K.; Niu, L. W.; Liu, Q.; Hao, Q. Protein Sci. 2006, 15, 761-773
5. Zhang, Y.; Colabroy, K. L.; Begley, T. P.; Ealick, S. E. Biochemistry 2005, 44, 7632-7643
6. Bassan, A.; Borowski, T.; Siegbahn, P. E. M. Dalton Trans. 2004, 3153-3162
7. Siegbahn, P. E. M.; Haeffner, F. J. Am. Chem. Soc. 2004, 126, 8919-8932
8. Deeth, R. J.; Bugg, T. D. H. J. Biol. Inorg. Chem. 2003, 8, 409-418
9. Spence, E. L.; Langley, G. J.; Bugg, T. D. H. J. Am. Chem. Soc. 1996, 118, 8336-8343
10. Kovaleva, E. G.; Lipscomb, J. D. Science 2007, 316, 453-457
11. Poddel'sky, A. I.; Cherkasov, V. K.; Abakumov, G. A. Coord. Chem. Rev. 2009, 253, 291-324
12. Chun, H.; Bill, E.; Bothe, E.; Weyhermuller, T.; Wieghardt, K. Inorg. Chem. 2002, 41, 5091-5099
13. Min, K. S.; Weyhermuller, T.; Wieghardt, K. Dalton Trans. 2003, 1126-1132
14. Min, K. S.; Weyhermuller, T.; Wieghardt, K. Dalton Trans. 2004, 178-186
15. Mukherjee, S.; Weyhermuller, T.; Bill, E.; Wieghardt, K.; Chaudhuri, P. Inorg. Chem. 2005, 44, 7099-7108
16. Chun, H. P.; Bill, E.; Weyhermuller, T.; Wieghardt, K. Inorg. Chem. 2003, 42, 5612-5620
17. Chun, H.; Verani, C. N.; Chaudhuri, P.; Bothe, E.; Bill, E.; Weyhermuller, T.; Wieghardt, K. Inorg. Chem. 2001, 40, 4157-4166
18. Chun, H.; Weyhermuller, T.; Bill, E.; Wieghardt, K. Angew. Chem., Int. Ed. 2001, 40, 2489-2492
19. Attia, A. S.; Conklin, B. J.; Lange, C. W.; Pierpont, C. G. Inorg. Chem. 1996, 35, 1033-1038
20. Koch, W. O.; Schunemann, V.; Gerdan, M.; Trautwein, A. X.; Kruger, H. J. Chem.-Eur. J. 1998, 4, 1255-1265
21. Pierpont, C. G. Coord. Chem. Rev. 2001, 219, 415-433
22. Mehn, M. P.; Fujisawa, K.; Hegg, E. L.; Que, L., Jr. J. Am. Chem. Soc. 2003, 125, 7828-7842
23. Park, H.; Baus, J. S.; Lindeman, S. V.; Fiedler, A. T. Inorg. Chem. 2011, 50, 11978-11989
24. The τ-value is 0.0 in idealized square-planar geometries and 1.0 in idealized trigonal-bipyramidal geometries. See: Addison, A. W.; Rao, T. N.; Reedijk, J.; Vanrijn, J.; Verschoor, G. C. J. Chem. Soc., Dalton Trans. 1984, 1349-1356
25. Bennett, B. In Metals in Biology: Applications of High-resolution EPR to Metalloenzymes; Hanson, G.; Berliner, L., Eds.; Springer: New York, 2010; Vol. 29, pp 345-370.
26. Jang, H. G.; Cox, D. D.; Que, L., Jr. J. Am. Chem. Soc. 1991, 113, 9200-9204
27. Cox, D. D.; Que, L., Jr. J. Am. Chem. Soc. 1988, 110, 8085-8092
28. Bruijnincx, P. C. A.; Lutz, M.; Spek, A. L.; Hagen, W. R.; Weckhuysen, B. M.; vanKoten, G.; Gebbink, R. J. M. K. J. Am. Chem. Soc. 2007, 129, 2275-2286
29. Brown, S. N. Inorg. Chem. 2012, 51, 1251-1260