Spectroscopic studies of the oxidation of ferric CYP153A6 by peracids: Insights into P450 higher oxidation states

Archives of Biochemistry and Biophysics

Volumn 493, Issue 2, 2010, Pages 184-191

  Spolitak, Tatyana ^a   Funhoff, Enrico G ^b   Ballou, David P ^a  

^a UNIVERSITY OF MICHIGAN MEDICAL SCHOOL   (United States)

^b ETH ZURICH   (Switzerland)

Author keywords

Alkane hydroxylation; Cpd I; Cpd II; Cyp153A6; Cytochrome P450; Ferryl intermediates; Peracids

Indexed keywords

3 CHLOROPERBENZOIC ACID; ASCORBIC ACID; CAMPHOR 5 MONOOXYGENASE; CYTOCHROME C PEROXIDASE; CYTOCHROME P450; CYTOCHROME P450 153A6; HEPTANE; HEPTANOL; OXIDIZING AGENT; PERACID; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE DEHYDROGENASE; UNCLASSIFIED DRUG;

ARTICLE; BIOCATALYST; BIOREMEDIATION; CHEMICAL REACTION; CONTROLLED STUDY; ELECTRON SPIN RESONANCE; ENZYME ACTIVE SITE; ENZYME METABOLISM; ENZYME MODIFICATION; ENZYME SUBSTRATE; HYDROXYLATION; MYCOBACTERIUM; NONHUMAN; PH; PRIORITY JOURNAL; PSEUDOMONAS PUTIDA; REACTION ANALYSIS; SPECTROSCOPY; TEMPERATURE DEPENDENCE; ULTRAVIOLET SPECTROPHOTOMETRY;

CHLOROBENZOATES; CYTOCHROME P-450 ENZYME SYSTEM; FERRIC COMPOUNDS; HYDROGEN-ION CONCENTRATION; MYCOBACTERIUM; OXIDANTS; OXIDATION-REDUCTION;

EID: 72949088406     PISSN: 00039861     EISSN: 10960384     Source Type: Journal    
DOI: 10.1016/j.abb.2009.10.014     Document Type: Article

References (50)

1. Ortiz de Montellano P. Cytochrome P450: Structure, Mechanism and Biochemistry (1995), Plenum, NY
2. Hayaishi O. Molecular Mechanisms of Oxygen Activation (1974), Academic Press, New York
3. Groves J.T. Proc. Natl. Acad. Sci. USA 100 (2003) 3569-3574
4. Coon M.J. Biochem. Biophys. Res. Commun. 312 (2003) 163-168
5. Davydov R., Makris T.M., Kofman V., Werst D.E., Sligar S.G., and Hoffman B.M. J. Am. Chem. Soc. 123 (2001) 1403-1415
6. Sligar S.G., Makris T.M., and Denisov I.G. Biochem. Biophys. Res. Commun. 338 (2005) 346-354
7. Newcomb M., and Chandrasena R.E. Biochem. Biophys. Res. Commun. 338 (2005) 394-403
8. Nam W., Ryu Y.O., and Song W.J. J. Biol. Inorg. Chem. 9 (2004) 654-660
9. McLain J., Lee J., and Groves J.T. Biomimetic oxidations related to cytochrome P450: metal-oxo and metal-peroxo intermediates. In: Meunier B. (Ed). Biomimetic Oxidations Catalyzed by Transition Metal Complexes (2000), Imperial College Press, London 91-170
10. Egawa T., Shimada H., and Ishimura Y. Biochem. Biophys. Res. Commun. 201 (1994) 1464-1469
11. Kellner D.G., Hung S.C., Weiss K.E., and Sligar S.G. J. Biol. Chem. 277 (2002) 9641-9644
12. Sono M., Roach M.P., Coulter E.D., and Dawson J.H. Chem. Rev. 96 (1996) 2841-2887
13. Issak I.S., and Dawson J.H. Haem iron-containing peroxidases. In: Ballou D.P. (Ed). Essays in Biochemistry (1999), Portland Press, Princeton, NJ 51-69
14. Spolitak T., Dawson J.H., and Ballou D.P. J. Biol. Chem. 280 (2005) 20300-20309
15. Spolitak T., Dawson J.H., and Ballou D.P. J. Inorg. Biochem. 100 (2006) 2034-2044
16. Schünemann V., Lendzian F., Jung C., Contzen J., Barra A.L., Sligar S.G., and Trautwein A.X. J. Biol. Chem. 279 (2004) 10919-10930
17. Schünemann V., Jung C., Terner J., Trautwein A.X., and Weiss R. J. Inorg. Biochem. 91 (2002) 586-596
18. Jung C., Schunemann V., and Lendzian F. Biochem. Biophys. Res. Commun. 338 (2005) 355-364
19. Raner G.M., Thompson J.I., Haddy A., Tangham V., Bynum N., Ramachandra Reddy G., Ballou D.P., and Dawson J.H. J. Inorg. Biochem. 100 (2006) 2045-2053
20. Spolitak T., Dawson J.H., and Ballou D.P. J. Biol. Inorg. Chem. 13 (2008) 599-611
21. Hessenauer-Ilicheva N., Franke A., Meyer D., and Woggon W.D. Chem. Eur. J. 15 (2009) 2941-2959
22. Khavrutskii I.V., Musaev D.G., and Morokuma K. Inorg. Chem. 44 (2005) 306-315
23. Yamaguchi K., Watanabe Y., and Morishima I. J. Chem. Soc. Chem. Commun. (1992) 1709-1710
24. Machii K., Watanabe Y., and Morishima I. J. Am. Chem. Soc. 117 (1995) 6691-6697
25. Matsui T., Nagano S., Ishimori K., Watanabe Y., and Morishima I. Biochemistry 35 (1996) 13118-13124
26. Wiseman B., Colin J., Smith A.T., Ivancich A., and Loewen P.C. J. Biol. Inorg. Chem. 14 (2009) 801-811
27. Ichikawa Y., Nakajima H., and Watanabe Y. Chembiochem 7 (2006) 1582-1589
28. Brittain T., Baker A.R., Butler C.S., Little R.H., Lowe D.J., Greenwood C., and Watmough N.J. Biochem. J. 326 (1997) 109-115
29. Green A.J., Rivers S.L., Cheeseman M., Reid G.A., Quaroni L.G., Macdonald I.D., Chapman S.K., and Munro A.W. J. Biol. Inorg. Chem. 6 (2001) 523-533
30. Hawkes D.B., Adams G.W., Burlingame A.L., Ortiz de Montellano P.R., and De Voss J.J. J. Biol. Chem. 277 (2002) 27725-27732
31. McLean M.A., Maves S.A., Weiss K.E., Krepich S., and Sligar S.G. Biochem. Biophys. Res. Commun. 252 (1998) 166-172
32. Funhoff E.G., Bauer U., Garcia-Rubio I., Witholt B., and van Beilen J.B. J. Bacteriol. 188 (2006) 5220-5227
33. Asperger O., Naumann A., and Lkeber H.P. FEMS Microbiol. Lett. 11 (1981) 309-312
34. Eremina S.S., Asperger O., and Kleber H.P. Mikrobiologiia 56 (1987) 764-769
35. van Beilen J.B., Funhoff E.G., van Loon A., Just A., Kaysser L., Bouza M., Holtackers R., Rothlisberger M., Li Z., and Witholt B. Appl. Environ. Microbiol. 72 (2006) 59-65
36. Li Z., and Chang D.L. Curr. Org. Chem. 8 (2004) 1647-1658
37. van Beilen J.B., Holtackers R., Luscher D., Bauer U., Witholt B., and Duetz W.A. Appl. Environ. Microbiol. 71 (2005) 1737-1744
38. Urlacher V.B., and Schmid R.D. Curr. Opin. Chem. Biol. 10 (2006) 156-161
39. Cotton M.L., Dunford H.B., and Raycheba J.M. Can. J. Biochem. 51 5 (1973) 627-631
40. Bevington P.R. Data Reduction and Error Analysis for the Physical Sciences (1996), McGraw-Hill Inc., New York pp. 235-242
41. Palcic M.M., Rutter R., Araiso T., Hager L.P., and Dunford H.B. Biochem. Biophys. Res. Commun. 94 (1980) 1123-1127
42. Rutter R., Hager L.P., Dhonau H., Hendrich M., Valentine M., and Debrunner P. Biochemistry 23 (1984) 6809-6816
43. Schunemann V., Jung C., Trautwein A.X., Mandon D., and Weiss R. FEBS Lett. 479 (2000) 149-154
44. Prasad S., Mazumdar S., and Mitra S. FEBS Lett. 477 (2000) 157-160
45. Griffin B.W., and Peterson J.A. Biochemistry 11 (1972) 4740-4746
46. Atkins W.M., and Sligar S.G. J. Biol. Chem. 263 (1988) 18842-18849
47. Matsui T., Ozaki S., and Watanabe Y. J. Am. Chem. Soc. 121 (1999) 9952-9957
48. Xu F., Bell S.G., Lednik J., Insley A., Rao Z., and Wong L.L. Angew. Chem. Int. Ed. Engl. 44 (2005) 4029-4032
49. Xu F., Bell S.G., Rao Z., and Wong L.L. Protein Eng. Des. Sel. 20 (2007) 473-480
50. Munro A.W., Girvan H.M., and McLean K.J. Biochim. Biophys. Acta 1770 (2007) 345-359