High-valent iron in chemical and biological oxidations

Journal of Inorganic Biochemistry

Volumn 100, Issue 4, 2006, Pages 434-447

  Groves, John T ^a  

^a PRINCETON UNIVERSITY   (United States)

Author keywords

AlkB; Chloroperoxidase; Cytochrome P450; Fenton; Ferryl; Mechanism; Oxygen rebound; sMMO

Indexed keywords

CHLORIDE PEROXIDASE; CYCLOHEXANOL DERIVATIVE; CYTOCHROME P450; FERROUS ION; HYDROGEN PEROXIDE; HYDROXYL RADICAL; IRON DERIVATIVE; METALLOPORPHYRIN; METHANE MONOOXYGENASE; OXYGENASE; PEROXYNITRITE; PORPHYRIN DERIVATIVE; UNSPECIFIC MONOOXYGENASE;

ATOM; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL PROCEDURES; CHEMICAL REACTION; DYNAMICS; ELECTRON SPIN RESONANCE; EPIMERIZATION; FENTON REACTION; HYDROXYLATION; MOLECULAR PROBE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; OXYGENATION; REACTION ANALYSIS; REVIEW;

ALKANE 1-MONOOXYGENASE; CATALYSIS; CYTOCHROME P-450 ENZYME SYSTEM; HYDROGEN PEROXIDE; HYDROXYLATION; IRON; LIGANDS; METALLOPORPHYRINS; MODELS, BIOLOGICAL; MODELS, CHEMICAL; NONHEME IRON PROTEINS; OXIDATION-REDUCTION; OXYGENASES; PEROXYNITROUS ACID;

EID: 33645875048     PISSN: 01620134     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jinorgbio.2006.01.012     Document Type: Review

References (115)

1. Groves J.T. Proc. Nat. Acad. Sci. USA 100 (2003) 3569-3574
2. Groves J.T. Models and mechanisms of cytochrome P-450 action. In: Ortiz de Montellano P.R. (Ed). Cytochrome P450: Structure, Mechanism, and Biochemistry. third ed. (2004), Kluwer Academic/Plenum, New York 1-44 (Chapter 1)
3. Guengerich F.P. Drug Metab. Rev. 36 (2004) 159-197
4. Ortiz de Montellano P.R., and De Voss J.J. Nat. Prod. Rep. 19 (2002) 477-493
5. Kryatov S.V., Rybak-Akimova E.V., and Schindler S. Chem. Rev. 105 (2005) 2175-2226
6. Kopp D.A., and Lippard S.J. Curr. Opin. Chem. Biol. (2002) 568-576
7. van Beilen J.B., and Funhoff E.G. Curr. Opin. Biotechnol. 16 (2005) 308-314
8. Bertrand E., Sakai R., Rozhkova-Novosad E., Moe L., Fox B.G., Groves J.T., and Austin R.N. J. Inorg. Biochem. 99 (2005) 1998-2006
9. Krebs C., Price J.C., Baldwin J., Saleh L., Green M.T., and Bollinger J.M. Inorg. Chem. 44 (2005) 742-757
10. Bollinger J.M., Price J.C., Hoffart L.M., Barr E.W., and Krebs C. Eur. J. Inorg. Chem. (2005) 4245-4254
11. Walling C. Acc. Chem. Res. 31 (1998) 155-157
12. Fenton H.J.H. J. Chem. Soc. 64 (1894) 899
13. Walling C. Acc. Chem. Res 8 (1975) 125-131
14. Goldstein S., Meyerstein D., and Czapski G. Free Rad. Biol. Med. 15 (1993) 435-445
15. Koppenol W.H. Free Rad. Biol. Med. 15 (1993) 645-651
16. Haber F., and Weiss J. Proc. R. Soc. Lond. 147 (1934) 332
17. Bray W.C., and Gorin M.H. J. Am. Chem. Soc. 54 (1932) 2124
18. Groves J.T., and Van Der Puy M. J. Am. Chem. Soc. 98 (1976) 5290
19. Groves J.T., and McClusky G.A. J. Am. Chem. Soc. 98 (1976) 859-861
20. Conocchi Tj., Hamilton E.J., and Sutin N. J. Am. Chem. Soc. 87 (1965) 926
21. Logager T., Holcman J., Sehested K., and Pedersen T. Inorg. Chem. 31 (1992) 3523-3529
22. Pestovsky O., and Bakac A. J. Am. Chem. Soc. 126 (2004) 13757-13764
23. Jensen M.P., Costas M., Ho R.Y.N., Kaizer J., Payeras A.M.I., Munck E., Que L., Rohde J.U., and Stubna A. J. Am. Chem. Soc. 127 (2005) 10512-10525
24. Rohde J.U., In J.H., Lim M.H., Brennessel W.W., Bukowski M.R., Stubna A., Munck E., Nam W., and Que L. Science 299 (2003) 1037-1039
25. Pestovsky O., Stoian S., Bominaar E.L., Shan X.P., Munck E., Que L., and Bakac A. Angew. Chem. Int. Edit. 44 (2005) 6871-6874
26. Kremer M.L. J. Phys. Chem. A 107 (2003) 1734-1741
27. Groves J.T., and Jin N. J. Am. Chem. Soc. 121 (1999) 2923-2924
28. Jin N., Bourassa J.L., Tizio S.C., and Groves J.T. Angew. Chem. 39 (2000) 3849-3851
29. Buda F., Ensing B., Gribnau M.C.M., and Baerends E.J. Chem. Eur. J. 7 (2001) 2775-2783
30. Ensing B., Buda F., Gribnau M.C.M., and Baerends E.J. J. Am. Chem. Soc. 126 (2004) 4355-4365
31. Barton D.H.R. Tetrahedron 54 (1998) 5805-5817
32. Barton D.H.R., Beviere S.D., Chavasiri W., Doller D., Liu W.G., and Reibenspies J.H. New J. Chem. 16 (1992) 1019-1029
33. Stavropoulos P., Celenligil-Cetin R., and Tapper A.E. Acc. Chem. Res. 34 (2001) 745-752
34. Minisci F., Fontana F., Araneo S., and Recupero F. J. Chem. Soc. Chem. Commun. (1994) 1823-1824
35. Snelgrove D.W., MacFaul P.A., Ingold K.U., and Wayner D.D.M. Tetrahedron Lett. 37 (1996) 823-826
36. Mayer J.M. Ann. Rev. Phys. Chem. 55 (2004) 363-390
37. Goldsmith C.R., Cole A.P., and Stack T.D.P. J. Am. Chem. Soc. 127 (2005) 9904-9912
38. Goldsmith C.R., Jonas R.T., and Stack T.D.P. J. Am. Chem. Soc. 124 (2002) 83-96
39. Lucas R.L., Powell D.R., and Borovik A.S. J. Am. Chem. Soc. 127 (2005) 11596-11597
40. MacBeth C.E., Gupta R., Mitchell-Koch K.R., Young V.G., Lushington G.H., Thompson W.H., Hendrich M.P., and Borovik A.S. J. Am. Chem. Soc. 126 (2004) 2556-2567
41. MacBeth C.E., Golombek A.P., Young V.G., Yang C., Kuczera K., Hendrich M.P., and Borovik A.S. Science 289 (2000) 938-941
42. Lim M.H., Rohde J.U., Stubna A., Bukowski M.R., Costas M., Ho R.Y.N., Munck E., Nam W., and Que L. Proc. Nat. Acad. Sci. USA 100 (2003) 3665-3670
43. Price J.C., Barr E.W., Hoffart L.M., Krebs C., and Bollinger J.M. Biochemistry 44 (2005) 8138-8147
44. Riggs-Gelasco P.J., Price J.C., Guyer R.B., Brehm J.H., Barr E.W., Bollinger J.M., and Krebs C. J. Am. Chem. Soc. 126 (2004) 8108-8109
45. Bollinger J.M., Price J.C., Barr E.W., Tirupati B., and Krebs C. J. Inorg. Biochem. 96 (2003) 63
46. Sundaramoorty M., Terner J., and Poulos T.L. Structure 3 (1995) 1367-1377
47. Manoj K.M., and Hager L.P. Biochim. Biophys. Acta 1547 (2001) 408-417
48. Stone K.L., Behan R.K., and Green M.T. Proc. Nat. Acad. Sci. USA 102 (2005) 16563-16565
49. Green M.T., Dawson J.H., and Gray H.B. Science 304 (2004) 1653-1656
50. Santhanam L., and Dordick J.S. Biocatal. Biotransfor. 20 (2002) 265-274
51. Rantwijk F., and Sheldon R.A. Curr. Opin. Biotechnol. 11 (2000) 554-564
52. Van Beilen J.B., and Li Z. Curr. Opin. Biotechnol. 13 (2002) 338-344
53. Glieder A., Farinas E.T., and Arnold F.H. Nat. Biotechnol. 20 (2002) 1135-1139
54. Crane B.R., Arvai A.S., Ghosh S., Getzoff E.D., Stuehr D.J., and Tainer J.A. Biochemistry 39 (2000) 4608-4621
55. Raman C.S., Li H.Y., Martasek P., Southan G., Masters B.S.S., and Poulos T.L. Biochemistry 40 (2001) 13448-13455
56. Li H.Y., Raman C.S., Martasek P., Masters B.S.S., and Poulos T.L. Biochemistry 40 (2001) 5399-5406
57. Groves J.T., and Marla S.S. J. Am. Chem. Soc. 117 (1995) 9578-9579
58. Davies J.A., et al. Selective Hydrocarbon Activation: Principle and Progress (1994), VCH, New York
59. Groves J.T., and Han Y.-Z. Models and mechanisms of cytochrome P450 action. In: Ortiz de Montellano P.R. (Ed). Cytochrome P-450. Structure, Mechanism and Biochemistry (1995), Plenum Press, New York
60. Watanabe Y. In: Kadish K. (Ed). The Porphyrin Encyclopedia vol. 4 (1999) 97-116
61. Groves J.T., Nemo T.E., and Myers R.S. J. Am. Chem. Soc. 101 (1979) 1032-1033
62. Groves J.T., Haushalter R.C., Nakamura M., Nemo T.E., and Evans B.J. J. Am. Chem. Soc. 102 (1981) 2884-2886
63. Groves J.T., and Watanabe Y. J. Am. Chem. Soc. 110 (1988) 8443-8452
64. Nam W., Goh Y.M., Lee Y.J., Lim M.H., and Kim C. Inorg. Chem. 38 (1999) 3238
65. Groves J.T., Quinn R., Mcmurry T.J., Lang G., and Boso B. J. Chem. Soc., Chem. Commun. (1984) 1455
66. Penner-Hahn J.E., McMurry T.J., Renner M., Latos-Grazynsky L., Eble K.S., Davis I.M., Balch A.L., Groves J.T., Dawson J.R., and Hodgson K.O. J. Biol. Chem. 258 (1983) 12761-12764
67. Penner-Hahn J.E., Eble K.S., McMurry T.J., Renner M., Balch A.L., Groves J.T., Dawson J.H., and Hodgson K.O. J. Am. Chem. Soc. 108 (1986) 7819-7825
68. Boso B., Lang G., Mcmurry T.J., and Groves J.T. J. Chem. Phys. 79 (1983) 1122
69. Jayaraj K., Gold A., Austin R.N., Ball L.M., Terner J., Mandon D., Weiss R., Fischer J., DeCian A., Bill E., Muther M., Schunemann V., and Trautwein A.X. Inorg. Chem. 36 (1997) 4555-4566
70. Ayougou K., Mandon D., Fischer J., Weiss R., Muther M., Schunemann V., Trautwein A.X., Bill E., Terner J., Jayaraj K., Gold A., and Austin R.N. Chem. Eur. J. 2 (1996) 1159-1163
71. Jayaraj K., Terner J., Gold A., Roberts D.A., Austin R.N., Mandon D., Weiss R., Bill E., Muther M., and Trautwein A.X. Inorg. Chem. 35 (1996) 1632-1640
72. Jayaraj K., Gold A., Austin R.N., Mandon D., Weiss R., Terner J., Bill E., Muther M., and Trautwein A.X. J. Am. Chem. Soc. 117 (1995) 9079-9080
73. Muther M., Bill E., Trautwein A.X., Mandon D., Weiss R., Gold A., Jayaraj K., and Austin R.N. Hyperfine Interact. 91 (1994) 803-808
74. Groves J.T., and McClusky G.A. J. Am. Chem. Soc. 98 (1976) 859
75. Gelb M.H., Heimbrook D.C., Malkonen P., and Sligar S.G. Biochemistry 21 (1982) 370-377
76. Groves J.T., and Adhyam D.V. J. Am. Chem. Soc. 106 (1984) 2177-2181
77. Vaz A.D.N., McGinnity D.F., and Coon M.J. Proc. Natl. Acad. Sci. USA 95 (1998) 3555-3560
78. Newcomb M., Hollenberg P.F., and Coon M.J. Arch. Biochem. Biophys. 409 (2003) 72-79
79. Veeger C. J. Inorg. Biochem. 9 (2002) 35-45
80. Shaik S., de Visser S.P., and Kumar D. J. Biol. Inorg. Chem. 9 (2004) 661-668
81. Bach R.D., and Dmitrenko O. J. Am. Chem. Soc. 128 (2006) 1474-1488
82. Davydov R., Markis T.M., Kofman V., Werst D.E., Sligar S.G., and Hoffman B.M. J. Am. Chem. Soc. 123 (2001) 1413-1415
83. Auclaire K., Hu Z., Little D.M., Ortiz de Montellano P.R., and Groves J.T. J. Am. Chem. Soc. 124 (2002) 6020-6027
84. Newcomb M., Shen R.N., Lu Y., Coon M.J., Hollenberg P.F., Kopp D.A., and Lippard S.J. J. Am. Chem. Soc. 124 (2002) 6879-6886
85. Rollick K.L., and Kochi J.K. J. Am. Chem. Soc. 104 (1982) 1319-1330
86. Newcomb M., Shen R., Lu Y., Coon M.J., Hollenberg P.F., Kopp D.A., and Lippard S.J. J. Am. Chem. Soc. 128 (2006) 1394
87. The data shown is typical of analyses of three cytochrome P450 2B4/norcarane reaction mixtures provided by M. Newcomb (see Ref. [84]) and analyzed by Dorothy Little at Princeton University.
88. He X., and Ortiz de Montellano P.R. J. Biol. Chem. 279 (2004) 39479-39484
89. He X., and Ortiz de Montellano P.R. J. Org. Chem. 69 (2004) 5684-5689
90. Jiang Y., He X., and Ortiz de Montellano P.R. Biochemistry 45 (2006) 533-542
91. Newcomb M., and Toy P.H. Acc. Chem. Res 33 (2000) 449-455
92. Chandrasena R.E.P., Vatsis K.P., Coon M.J., Hollenberg P.F., and Newcomb M. J. Am. Chem. Soc. 126 (2004) 115-126
93. Shaik S., de Visser S.P., Ogliaro F., Schwarz H., and Schröder D. Curr. Opin. Chem. Biol. (2002) 556-567
94. Shaik S., Kumar D., de Visser S.P., Altun A., and Thiel W. Chem. Rev. 105 (2005) 2279-2328
95. Hirao H., Kumar D., Thiel W., and Shaik S. J. Am. Chem. Soc. 127 (2005) 13007-13018
96. Shaik S., Cohen S., de Visser S.P., Sharma P.K., Kumar D., Kozuch S., Ogliaro F., and Danovich D. Eur. J. Inorg. Chem. (2004) 207-226
97. Dowers T.S., Rock D.A., Rock D.A., and Jones J.P. J. Am. Chem. Soc. 126 (2004) 8868-8869
98. Li C., Wu W., Kumar D., and Shaik S. J. Am. Chem. Soc. 128 (2006) 394-395
99. Marla S.S., Lee J., and Groves J.T. Proc. Natl. Acad. Sci. USA 94 (1997) 14243-14248
100. Beckman J.S., and Koppenol W.H. Am. J. Physiol. 271 (1996) C1424-C1437
101. Lee J., Hunt J.A., and Groves J.T. Bioorg. Med. Chem. Lett. 7 (1997) 2913-2918
102. Groves J.T. Curr. Opin. Chem. Biol. 3 (1999) 226-235
103. Lee J., Hunt J.A., and Groves J.T. J. Am. Chem. Soc. 120 (1998) 6053-6061
104. Hunt J.A., Lee J., and Groves J.T. Chem. Biol. 4 (1997) 845-858
105. Stern M.K., Jensen M.P., and Kramer K. J. Am. Chem. Soc. 118 (1996) 8735-8736
106. Lee J.., Hunt J.A., and Groves J.T. J. Am. Chem. Soc. 120 (1998) 7493-7501
107. Shimanovich R., and Groves J.T. Arch. Biochem. Biophys. 387 (2001) 307-317
108. Szabo C., Mabley J.G., Moeller S.M., Shimanovich R., Pacher P., Virag L., Soriano F.G., Van Duzer J.H., Williams W., Salzman A.L., and Groves J.T. Mol. Med. 8 (2002) 571-580
109. Fox B.G., Lyle K.S., and Rogge C.E. Acc. Chem. Res 37 (2004) 421-429
110. Tshuva E.Y., and Lippard S.J. Chem. Rev. 104 (2004) 987-1011
111. Leahy J.G., Batchelor P.J., and Morcomb S.M. FEMS Microbiol. Rev. 27 (2003) 449-479
112. Austin R.N., Chang H.-K., Zylstra G.J., and Groves J.T. J. Am. Chem. Soc. 122 (2000) 11747-11748
113. Brazeau B.J., Austin R.N., Tarr C., Groves J.T., and Lipscomb J.D. J. Am. Chem. Soc. 123 (2001) 11831-11837
114. Moe L.A., Hu Z.B., Deng D.Y., Austin R.N., Groves J.T., and Fox B.G. Biochemistry 43 (2004) 15688-15701
115. Austin R.N., Buzzi K., Kim E., Zylstra G.B., and Groves J.T. J. Biol. Inorg. Chem. (2003)