Modeling the haloperoxidases: Reversible oxygen atom transfer between bromide ion and an oxo-Mn(V) porphyrin

Journal of Inorganic Biochemistry

Volumn 101, Issue 11-12, 2007, Pages 1786-1797

  Lahaye, Dorothée ^a   Groves, John T ^a  

^a PRINCETON UNIVERSITY   (United States)

Author keywords

Bromoperoxidase; Chloroperoxidase; Cytochrome P450; Oxomanganese porphyrin; Redox potential

Indexed keywords

BROMIDE ION; CYTOCHROME P450; HALOPEROXIDASE; HYDROGEN PEROXIDE; MANGANESE; MANGANESE DIMETHYLIMIDAZOLIUM PORPHYRIN COMPLEX; OXYGEN; PEROXIDASE; PORPHYRIN DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ARTICLE; EQUILIBRIUM CONSTANT; MOLECULAR MODEL; OXIDATION REDUCTION POTENTIAL; PH; PROTON TRANSPORT; REACTION ANALYSIS; REDUCTION;

BROMIDES; ELECTRON TRANSPORT; HALOGENS; HYDROGEN-ION CONCENTRATION; KINETICS; MANGANESE COMPOUNDS; METALLOPORPHYRINS; MODELS, CHEMICAL; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; OXYGEN; PEROXIDASES;

KOBUS;

EID: 35348915993     PISSN: 01620134     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jinorgbio.2007.07.017     Document Type: Article

References (61)

1. Meunier B., de Visser S.P., and Shaik S. Chem. Rev. 104 (2004) 3947-3980
2. Groves J.T. In: Ortiz de Montellano P.R. (Ed). Cytochrome P450: Structure, Mechanism, and Biochemistry. third ed. Models and Mechanisms of Cytochrome P-450 action (2005), Kluwer Academic/Plenum, New York 1-44 (Chapter 1)
3. Denisov I.G., Makris T.M., Sligar S.G., and Schlichting I. Chem. Rev. 105 (2005) 2253-2327
4. Groves J.T. J. Inorg. Biochem. 100 (2006) 434-447
5. Spolitak T., Dawson J.H., and Ballou D.P. J. Biol. Chem. 280 (2005) 20300-20309
6. Butler A. Coord. Chem. Rev. 187 (1999) 17-35
7. Poulos T.L. In: Kadish K.M., Smith K.M., and Guilard R. (Eds). The Porphyrin Handbook. Peroxidase and Cytochrome P450 Structures (2000), Academic Press, San Diego 200-202 (Chapter 32)
8. Ligtenbarg A.G.J., Hage R., and Feringa B.L. Coord. Chem. Rev. 237 (2003) 89-101
9. Ortiz-Bermudez P., Hirth K.C., Srebotnik E., and Hammel K.E. Proc. Nat. Acad. Sci. USA 104 (2007) 3895-3900
10. Kaup B.-A., Piantini U., Wust M., and Schrader J. Appl. Microbiol. Biotechnol. 73 (2007) 1087-1096
11. Neidleman S.L. Biohalogenation: Principles, Basic Roles and Applications (1986), Halsted Press, New York
12. Griffin B.W. In: Everse J., Everse K.M., and Grisham M.B. (Eds). Peroxidases in Chemistry and Biology. Chloroperoxidase: A Review (1991), CRC Press, Boca Raton, FL 85-138 (Chapter 4)
13. Sundaramoorthy M., Mauro J.M., Sullivan A.M., Terner J., and Poulos T.L. Acta. Cryst. D 51 (1995) 842-844
14. Groves J.T. Proc. Nat. Acad. Sci. USA 100 (2003) 3569-3574
15. Woggon W.-D. Acc. Chem. Res. 38 (2005) 127-136
16. Manthey J.A., and Hager L.P. Biochemistry 28 (1989) 3052-3057
17. Butler A., and Walker J.V. Chem. Rev. 93 (1993) 1937-1944
18. Kuhnel K., Derat E., Terner J., Shaik S., and Schlichting I. Proc. Nat. Acad. Sc. USA 104 (2007) 99-104
19. Egawa T., Miki H., Ogura T., Makino R., Ishimura Y., and Kitagawa T. FEBS Lett. 305 (1992) 206-208
20. Stone K.L., Behan R.K., and Green M.T. Proc. Nat. Acad. Sci. USA 102 (2005) 16563-16565
21. Wagenknecht H.-A., and Woggon W.-D. Chem. Biol. 4 (1997) 367-372
22. Wagenknecht H.-A., Claude C., and Woggon W.-D. Helv. Chim. Acta 81 (1998) 1506-1520
23. Woggon W.-D., Wagenknecht H.-A., and Claude C. J. Inorg. Biochem. 83 (2001) 289-300
24. Libby R.D., Shedd A.L., Phipps A.K., Beachy T.M., and Gerstberger S.M. J. Biol. Chem. 267 (1992) 1769-1775
25. Colonna S., Gaggero N., Casella L., Carrea G., and Pasta P. Tetrahedron Asymm. 3 (1992) 95-106
26. Allain E.J., Hager L.P., Deng L., and Jacobsen E.N. J. Am. Chem. Soc. 115 (1993) 4415-4416
27. Hofrichter M., and Ullrich R. Appl. Microbiol. Biotechnol. 71 (2006) 276-288
28. Kuhnel K., Blankenfeldt W., Terner J., and Schlichting I. J. Biol. Chem. 281 (2006) 23990-23998
29. Wilson I., Bretscher K.R., Chea C.K., and Kelly H.C. J. Inorg. Biochem. 19 (1983) 345-357
30. Groves J.T., Kruper W.J., and Haushalter R.C. J. Am. Chem. Soc. 102 (1980) 6375-6377
31. Groves J.T., Watanabe Y., and McMurry T.J. J. Am. Chem. Soc. 105 (1983) 4489-4490
32. Labat G., and Meunier B. J. Chem. Soc., Chem. Commun. (1990) 1414-1416
33. Jin N., Bourassa J.L., Tizio S.C., and Groves J.T. Angew. Chem. Int. Ed. 39 (2000) 3849-3851
34. De Angelis F., Jin N., Car R., and Groves J.T. Inorg. Chem. 45 (2006) 4268-4276
35. Shimazaki Y., Nagano T., Takesue H., Ye B.-H., Tani F., and Naruta Y. Angew. Chem. Int. Ed. 43 (2004) 98-100
36. Gazda M., and Margerum D.W. Inorg. Chem. 33 (1994) 118-123
37. Tjahjono D.H., Akutsu T., Yoshioka N., and Inoue H. Biochim. Biophys. Acta 1472 (1999) 333-343
38. J. Crapo, Patent WO 00/43395, 2000.
39. Jin N., and Groves J.T. J. Am. Chem. Soc. 121 (1999) 2923-2924
40. Walker J.V., Morey M., Carlssom H., Davidson A., Stucky G.D., and Butler A. J. Am. Chem. Soc. 119 (1997) 6921-6922
41. Groves J.T., Lee J., and Marla S.S. J. Am. Chem. Soc. 119 (1997) 6269-6273
42. Nam W., Kim I., Lim M.H., Choi H.J., Lee J.S., and Jang H.G. Chem. Eur. J. 8 (2002) 2067-2070
43. Zhang R., Horner J.H., and Newcomb M. J. Am. Chem. Soc. 127 (2005) 6573-6582
44. Song W.J., Seo M.S., DeBeer G.S., Ohta T., Song R., Kang M.-J., Tosha T., Kitagawa T., Solomon E.I., and Nam W. J. Am. Chem. Soc. 129 (2007) 1268-1277
45. Gross Z., Golubkov G., and Simkhovich L. Angew. Chem. Int. Ed. 39 (2000) 4045-4047
46. Lansky D.E., Mandimutsira B., Ramdhanie B., Clausen M., Penner-Hahn J., Zvyagin S.A., Telser J., Krzystek J., Zhan R., Ou Z., Kadish K.M., Zakharov L., Rheingold A.L., and Goldberg D.P. Inorg. Chem. 44 (2005) 4485-4498
47. Palucki M., Finney N.S., Pospisil P.J., Guler M.L., Ishida T., and Jacobsen E.N. J. Am. Chem. Soc. 120 (1998) 948-954
48. Lee R.W., Nakagaki P.C., and Bruice T.C. J. Am. Chem. Soc. 111 (1989) 1368-1372
49. Anelli P.L., Banfi S., Legramandi F., Montanari F., Pozzi G., and Quici S. J. Chem. Soc. Perkin Trans I (1993) 1345-1357
50. De Carvalho M.-E., and Meunier B. Tetrahedron Lett. 24 (1983) 3621-3624
51. Meunier B., Guilmet E., De Carvalho M.-E., and Poilblanc R. J. Am. Chem. Soc. 106 (1984) 6668-6676
52. De Poorter B., Ricci M., Bortolini O., and Meunier B. J. Mol. Cat. 31 (1985) 221-224
53. Bortolini O., Ricci M., Meunier B., Friant P., Ascone I., and Goulon J. Nouv. J. Chem. 10 (1986) 39
54. Kerr J.A. In: Lide D.R. (Ed). Handbook of Chemistry and Physics. 84th ed. (2003-2004), CRC Press, Boca Raton
55. Huang L., and Ortiz de Montellano P.R. Biochem. Biophys. Res. Commun. 355 (2007) 581-586
56. Tumanov V.E., and Denisov E.T. Kinet. Catal. 45 (2004) 661-667
57. Stanbury D.M. Adv. Inorg. Chem. 33 (1989) 69-138
58. Hung M., and Bakac A. Inorg. Chem. 44 (2005) 9293-9298
59. Chen F.C., Cheng S.H., Yu C.H., Liu M.H., and Su Y.O. J. Electroanal. Chem. 474 (1999) 52-59
60. Morel F.M.M., and Groves J.T. Science 314 (2006) 1406
61. Dismukes G.C., Hecht M., Spiro T.G., Groves J.T., and Chianelli R.R. J. Inorg. Biochem. 101 (2007) vii-viii