A diiron(iv) complex that cleaves strong C-H and O-H bonds

Nature Chemistry

Volumn 1, Issue 2, 2009, Pages 145-150

  Wang, Dong ^a   Farquhar, Erik R ^a   Stubna, Audria ^b   Münck, Eckard ^b   Que, Lawrence ^a  

^a University of Minnesota   (United States)

^b CARNEGIE MELLON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; COORDINATION COMPOUND; CYCLOHEXANE; CYCLOHEXANE DERIVATIVE; HYDROGEN; IRON; METHANE MONOOXYGENASE; METHANOL; OXYGEN; OXYGENASE;

ARTICLE; BIOCATALYSIS; CHEMISTRY; CONFORMATION; METABOLISM; OXIDATION REDUCTION REACTION; X RAY ABSORPTION SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

BIOCATALYSIS; CARBON; COORDINATION COMPLEXES; CRYSTALLOGRAPHY, X-RAY; CYCLOHEXANES; HYDROGEN; IRON; METHANOL; MOLECULAR CONFORMATION; OXIDATION-REDUCTION; OXYGEN; OXYGENASES; X-RAY ABSORPTION SPECTROSCOPY;

EID: 67849118867     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.162     Document Type: Article

References (39)

1. Hanson, R. S. & Hanson, T. E. Methanotrophic bacteria. Microbiol. Rev. 60, 439-471 (1996).
2. Wallar, B. J. & Lipscomb, J. D. Dioxygen activation by enzymes containing binuclear non-heme iron clusters. Chem. Rev. 96, 2625-2657 (1996).
3. Merkx, M. et al. Dioxygen Activation and methane hydroxylation by soluble methane monooxygenase: A tale of two irons and three proteins. Angew. Chem. Int. Ed. 40, 2782-2807 (2001).
4. Balasubramanian, R. & Rosenzweig, A. C. Structural and mechanistic insights into methane oxidation by particulate methane monooxygenase. Acc. Chem. Res. 40, 573-580 (2007).
5. IV cluster. J. Am. Chem. Soc. 115, 6450-6451 (1993).
6. Liu, K. E. et al. Kinetic and spectroscopic characterization of intermediates and component interactions in reactions of methane monooxygenase from Methylococcus capsulatus (Bath). J. Am. Chem. Soc. 117, 10174-10185 (1995).
7. Nesheim, J. C. & Lipscomb, J. D. Large kinetic isotope effects in methane oxidation catalyzed by methane monooxygenase: Evidence for C-H bond cleavage in a reaction cycle intermediate. Biochemistry 35, 10240-10247 (1996).
8. 2 diamond core structure for the key intermediate Q of methane monooxygenase. Science 275, 515-518 (1997).
9. Ghosh, A. et al. Catalytically active μ-oxodiiron(IV) oxidants from iron(III) and dioxygen. J. Am. Chem. Soc. 127, 2505-2513 (2005).
10. 2] diamond core proposed for methane monooxygenase intermediate Q. Proc. Natl Acad. Sci. USA 104, 20713-20718 (2007).
11. Xu, J.-Y. et al. Iron(III) complexes with the ligand N′,N′'-bis[(2-pyridyl)-methyl] ethylenediamine (uns-penp) and its amide derivative N-acetyl-N′, N′-bis[(2-pyridyl)methyl]ethylenediamine (acetyl-uns-penp). Eur. J. Inorg. Chem. 1601-1610 (2006).
12. Kurtz, D. M. Jr Oxo- and hydroxo-bridged diiron complexes: A chemical perspective on a biological unit. Chem. Rev. 90, 585-606 (1990).
13. 3+ core. J. Am. Chem. Soc. 125, 15554-15570 (2003).
14. Norman, R. E. et al. (μ-Oxo)(μ-carboxylato)diiron(III) complexes with distinct iron sites. Consequences of the inequivalence and its relevance to dinuclear iron-oxo proteins. J. Am. Chem. Soc. 112, 1554-1562(1990).
15. Jackson, T. A. et al. Axial ligand effects on the geometric and electronic structures of nonheme oxoiron(IV) complexes. J. Am. Chem. Soc. 130, 12394-12407 (2008).
16. Rohde, J. U. et al. Nonheme oxoiron(IV) complexes of tris(2-pyridylmethyl)amine with cis-monoanionic ligands. Inorg. Chem. 45, 6435-6445 (2006).
17. Collins, M. J., Ray, K. & Que, L. Jr Electrochemical generation of a nonheme oxoiron(IV) complex. Inorg. Chem. 45, 8009-8011 (2006).
18. IVO complexes that can oxidize the C-H bonds of cyclohexane at room temperature. J. Am. Chem. Soc. 126, 472-473 (2004).
19. Kumar, D., de Visser, S. P., Sharma, P. K., Cohen, S. & Shaik, S. Radical clock substrates, their C-H hydroxylation mechanism by cytochrome P450, and other reactivity patterns: What does theory reveal about the clocks' behaviour? J. Am. Chem. Soc. 126, 1907-1920 (2004).
20. Kumar, D., de Visser, S. P. & Shaik, S. Oxygen economy of cytochrome P450: What is the origin of the mixed functionality as a dehydrogenase-oxidase enzyme compared with its normal function? J. Am. Chem. Soc. 126, 5072-5073 (2004).
21. Jin, Y. & Lipscomb, J. D. Desaturation reactions catalyzed by soluble methane monooxygenase. J. Biol. Inorg. Chem. 6, 717-725 (2001).
22. Griller, D. & Ingold, K. U. Free-radical clocks. Acc. Chem. Res. 13, 317-323 (1980).
23. Vollhardt, K. P. C. The reactions of alcohols and the chemistry of ethers, in Organic Chemistry 308-358 (W. H. Freeman, 1987).
24. Luo, Y.-R. in Comprehensive Handbook of Chemical Bond Energies 255-369 (Taylor & Francis, 2007).
25. Pestovsky, O. & Bakac, A. Reactivity of aqueous fe(IV) in hydride and hydrogen atom transfer reactions. J. Am. Chem. Soc. 126, 13757-13764 (2004).
26. IV=O: Spectroscopic identification and oxo group exchange. Angew. Chem. Int. Ed. 44, 6871-6874 (2005).
27. Jacobsen, F., Holcman, J. & Sehested, K. Reactions of the ferryl ion with some compounds found in cloud water. Int. J. Chem. Kinet. 30, 215-221 (1998).
28. Shaik, S., Hirao, H. & Kumar, D. Reactivity of high-valent iron-oxo species in enzymes and synthetic reagents: A tale of many states. Acc. Chem. Res. 40, 532-542 (2007).
29. Sastri, C. V. et al. Axial ligand tuning of a nonheme iron(IV)-oxo unit for hydrogen atom abstraction. Proc. Natl Acad. Sci. USA 104, 19181-19186 (2007).
30. IVO complexes: Fe-O bonding and its contributions to reactivity. J. Am. Chem. Soc. 129, 15983-15996 (2007).
31. Bernasconi, L., Louwerse, M. J. & Baerends, E. J. The role of equatorial and axial ligands in promoting the activity of non-heme oxidoiron(IV) catalysts in alkane hydroxylation. Eur. J. Inorg. Chem. 3023-3033 (2007).
32. Klinker, E. J. High-valent iron compounds supported by pentadentate ligands. PhD thesis, Univ. Minnesota-Twin Cities (2007).
33. Berben, L. A. & Peters, J. C. Dimanganese and diiron complexes of a binucleating cyclam ligand: Four-electron, reversible oxidation chemistry at high potentials. Inorg. Chem. 47, 11669-11679 (2008).
34. Berry, J. F., Bill, E., Bothe, E., Neese, F. & Wieghardt, K. Octahedral non-heme oxo and non-oxo Fe(IV) complexes: An experimental/ theoretical comparison. J. Am. Chem. Soc. 128, 13515-13528 (2006).
35. 2 diamond core: A terminal iron(IV)-oxo species generated from the oxidation of a bis(μ-oxo)diiron(III) complex. J. Am. Chem. Soc. 122, 3789-3790 (2000).
36. Brazeau, B. J. & Lipscomb, J. D. Kinetics and thermodynamics of methane monooxygenase compound Q formation and reaction with substrates. Biochemistry 39, 13503-13515 (2000).
37. Valentine, A. M., Stahl, S. S. & Lippard, S. J. Mechanistic studies of the reaction of reduced methane monooxgyenase hydroxylase with dioxygen and substrates. J. Am. Chem. Soc. 121, 3876-3887 (1999).
38. Fox, B. G., Lyle, K. S. & Rogge, C. E. Reactions of the diiron enzyme stearoyl-acyl carrier protein desaturase. Acc. Chem. Res. 37, 421-429 (2004).
39. Luo, Y.-R. in Comprehensive Handbook of Chemical Bond Energies 19-147 (Taylor & Francis, 2007).