Quantum chemical studies of C-H activation reactions by high-valent nonheme iron centers

Current Opinion in Chemical Biology

Volumn 13, Issue 1, 2009, Pages 89-98

  Ye, Shengfa ^a   Neese, Frank ^a  

^a UNIVERSITY OF BONN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

DIOXYGENASE; IRON COMPLEX;

CATALYSIS; CRYSTALLOGRAPHY; ENERGY TRANSFER; HYDROGEN BOND; MOLECULAR MODEL; QUANTUM CHEMISTRY; REACTION ANALYSIS; REVIEW;

ENZYME ACTIVATION; IRON; KINETICS; MIXED FUNCTION OXYGENASES; MODELS, MOLECULAR; QUANTUM THEORY;

EID: 65249122495     PISSN: 13675931     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cbpa.2009.02.007     Document Type: Review

References (47)

1. In: Ortiz de Montellano P.R. (Ed). Cytochrome P450: Structure, Mechanism and Biochemistry. 3rd ed. (2004), Kluwer Academic/Plenum Publisher, New York
2. 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., and Zhou J. Geometric and electronic structure/function correlation in non-heme iron enzymes. Chem Rev 100 (2000) 235-350
3. Krebs C., Fujimori D.G., Walsh C.T., and Bollinger Jr. J.M. Non-heme Fe(IV)-oxo intermediates. Acc Chem Rev 40 (2007) 484-492. This important review describes the state of the art in the experimental characterization of nonheme Fe(IV)-oxo intermediates.
4. Costas M., Mehn M.P., Jensen M.P., and Que Jr. L. Dioxygen activation at mononuclear nonheme iron active sites: enzymes, models, and intermediate. Chem Rev 104 (2004) 939-986
5. Que Jr. L. The road to non-heme oxoferryls and beyond. Acc Chem Rev 40 (2007) 493-500. This important paper describes the considerable progress that has been made in the synthetic modeling of high-valent nonheme iron centers.
6. Price J.C., Barr E.W., Tirupati B., Bollinger Jr. J.M., and Krebs C. The first direct characterization of a high-valent iron intermediate in the reaction of an α-ketoglutarate-dependent dioxygenase: a high-spin Fe(IV) complex in taurine/α-ketoglutarate dioxygenase (TauD) from Escherichia coli. Biochemistry 42 (2003) 7497-7508
7. Price J.C., Barr E.W., Glass T.E., Krebs C., and Bollinger Jr. J.M. Evidence for hydrogen abstraction from C1 of taurine by the high-spin Fe(IV) intermediate detected during oxygen activation by taurine:α-ketoglutarate dioxygenase (TauD). J Am Chem Soc 125 (2003) 13008-13009
8. Shaik S., Kumar D., de Visser S.P., Altun A., and Thiel W. Theoretical perspective on the structure and mechanism of cytochrome P450 enzymes. Chem Rev 105 (2005) 2279-2328
9. Neese F. Prediction of molecular properties and molecular spectroscopy with density functional theory: from fundamental theory to exchange-coupling. Coord Chem Rev 253 (2009) 526-563. This paper provides an essentially complete and self-contained description of the theory underlying density functional calculations with some emphasis on theoretical spectroscopy.
10. Schwabe T., and Grimme S. Towards chemical accuracy for the thermodynamics of large molecules: new hybrid density functional including non-local correlation effects. Phys Chem Chem Phys 8 (2006) 4398-4401
11. Siegbahn P.E.M. The performance of hybrid DFT for mechanisms involving transition metal complexes in enzymes. J Biol Inorg Chem 11 (2006) 695-701. This review describes how mechanistic questions in metalloprotein biochemistry can be addressed through the calculation of reaction and activation energies.
12. Bühl M., Reimann C., Pantazis D., Bredow T., and Neese F. Geometries of third-row transition-metal complexes from density-functional theory. J Chem Theory Comput 4 (2008) 1449-1459
13. Siegbahn P.E.M. Mechanism of metalloenzymes studied by quantum chemical methods. Q Rev Biophys 36 (2003) 91-145
14. Senn HM, Thiel W: QM/MM methods for biological systems. In Atomistic Approaches in Modern Biology. From Quantum Chemistry to Molecular Simulations, Edited by Reiher M, Topics Curr Chem 2007, 268:173-290. This extensive review describes the important advances that enable the calculation of metalloprotein reactions with full inclusion of the entire protein environment and the solvation shell.
15. Senn H.M., and Thiel W. QM/MM studies of enzymes. Curr Opin Chem Biol 11 (2007) 182-187
16. Jensen F. Introduction to Computational Chemistry (1999), Wiley, Chichester; New York 1-429
17. + in water/acetone mixtures. Inorg Chem 39 (2000) 5306-5317
18. 2+: an oxidant more powerful than P450?. J Am Chem Soc 127 (2005) 8026-8027
19. Hirao H., Kumar D., Que Jr. L., and Shaik S. Two-state reactivity in alkane hydroxylation by non-heme iron-oxo complexes. J Am Chem Soc 128 (2006) 8590-8606
20. IV{double bond, long}O oxidants. Chem Eur J 14 (2008) 1740-1756. This paper provides a very detailed study of the reactivity of triplet ground state synthetic Fe(IV)-oxo model complexes.
21. Schröder D., and Schwarz H. C-H and C-C bond activation by bare transition-metal oxide cations in the gas phase. Angew Chem Int Ed 34 (1995) 1973-1995
22. Fiedler A., Schröder D., Shaik S., and Schwarz H. Electronic structures and gas-phase reactivities of cationic late-transition-metal oxides. J Am Chem Soc 116 (1994) 10734-10741
23. Shaik S., Danovich D., Fiedler A., Schröder D., and Schwarz H. Two-state reactivity in organometallic gas-phase ion chemistry. Helv Chim Acta 78 (1995) 1393-1407
24. Griffith J.S. The Theory of Transition Metal Ions (1964), Cambridge University Press, Cambridge
25. Mayer J.M. Hydrogen atom abstraction by metal-oxo complexes: understanding the analogy with organic radical reactions. Acc Chem Res 31 (1998) 441-450
26. Decornez H., and Hammes-Schiffer S. Model proton-coupled electron transfer reactions in solution: predictions of rates, mechanisms, and kinetic isotope effects. J Phys Chem A 104 (2000) 9370-9384
27. Hamess-Schiffer S., and Soudackov A.V. Proton-coupled electron transfer in solutions, proteins, and electrochemistry. J Phys Chem B 112 (2008) 14108-14123. This paper describes the state of the art of modeling proton-coupled electron transfer reactions when classic transition state theory is no longer appropriate.
28. Neese F. Quantum chemical calculations of spectroscopic properties of metalloproteins and model compounds: EPR and Mössbauer properties. Curr Opin Chem Biol 7 (2003) 125-135
29. Neese F. A critical evaluation of DFT, including time-dependent DFT, applied to bioinorganic chemistry. J Biol Inorg Chem 11 (2006) 702-711
30. Hanauske-Abel H.M., and Günzler V. A stereochemical concept for the catalytic mechanism of prolylhydroxylase: applicability to classification and design of inhibitors. J Theor Biol 94 (1982) 421-455
31. Hirao H., Kumar D., Thiel W., and Shaik S. Two states and two more in the mechanism of hydroxylation and epoxidation by cytochrome P450. J Am Chem Soc 127 (2005) 13007-13018
32. cam: theory supports a two-state rebound mechanism. J Am Chem Soc 126 (2004) 4017-4034
33. Harvey J.N., Poli R., and Smith K.M. Understanding of transition metal complexes involving multiple spin states. Coord Chem Rev 238-239 (2003) 347-361
34. 2. J Am Chem Soc 124 (2002) 2454-2455
35. Shaik S., Hirao H., and Kumar D. Reactivity of high-valent iron-oxo species in enzymes and synthetic reagents: a tale of many states. Acc Chem Res 40 (2006) 532-542
36. Siegbahn P.E.M., and Borowski T. Modeling enzymatic reactions involving transition metals. Acc Chem Res 39 (2006) 729-738
37. de Visser S.P. Propene activation by the oxo-iron active species of taurine/α-ketoglutarate dioxygenase (TauD) enzyme. How does the catalysis compare to heme-enzyme?. J Am Chem Soc 128 (2006) 9813-9824
38. de Visser S.P. What factors influence the ratio of C-H hydroxylation versus C{double bond, long}C epoxidation by a non-heme cytochrome P450 biomimetic?. J Am Chem Soc 128 (2006) 15809-15818
39. Ensing B., Buda F., Gribnau M.C.M., and Baerends E.J. Methane-to-methanol oxidation by the hydrated iron(IV) oxo species in aqueous solution: a combined DFT and Car-Parrinello molecular dynamics study. J Am Chem Soc 126 (2004) 4355-4365
40. Bernasconi L., Louwerse M.L., and 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 (2007) 3023-3033
41. 2+. Eur J Inorg Chem (2008) 1672-1681. This paper provides a creative view on the reactivity of nonheme iron(IV) centers.
42. 2+ complexes with triplet and quintet ground states using multireference ab initio and density functional theory methods. J Inorg Biochem 100 (2006) 716-726
43. Schöneboom J., Neese F., and Thiel W. Towards identification of the compound I reactive intermediate in cytochrome P450 chemistry: a QM/MM study of its EPR and Mössbauer parameters. J Am Chem Soc 127 (2005) 5840-5853
44. Ghosh A., Tangen E., Ryeng E., and Taylor P.R. Electronic structure of high-spin iron(IV) complexes. Eur. J. Inorg. Chem. 23 (2004) 4555-4560
45. Decker A., Rhode J.U., Klinker E.J., Wong S.D., Que Jr. L., and Solomon E.I. Spectroscopic and quantum chemical studies on low-spin Fe-IV{double bond, long}O complexes: Fe-O bonding and its contributions to reactivity. J Am Chem Soc 129 (2007) 15983-15996. This paper provides an analysis of the spectroscopic properties of Fe(IV)-oxo complexes and correlates spectroscopy and reactivity.
46. Riggs-Gelasco P.J., Price J.C., Guyer R.B., Brehm J.H., Barr E.W., Bollinger Jr. J.M., and Krebs C. EXAFS spectroscopic evidence for an Fe{double bond, long}O unit in the Fe(IV) intermediate observed during oxygen action by taurine: α-ketoglutarate dioxygenase. J Am Chem Soc 126 (2004) 8108-8109
47. Neidig M.L., Decker A., Choroba O.W., Huang F., Kavana M., Moran G.R., Spencer J.B., and Solomon E.I. Spectroscopic and electronic structure studies of aromatic electrophilic attack and hydrogen-atom abstraction by non-heme iron enzymes. Proc Natl Acad Sci U S A 103 (2006) 12966-12973