Superoxide-mediated formation of tyrosine hydroperoxides and methionine sulfoxide in peptides through radical addition and intramolecular oxygen transfer

Journal of Biological Chemistry

Volumn 284, Issue 22, 2009, Pages 14723-14733

  Nagy, Péter ^a   Kettle, Anthony J ^a   Winterbourn, Christine C ^a  

^a UNIVERSITY OF OTAGO   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE EFFECT; AMINO GROUP; CONJUGATE ADDITION; ELECTRON TRANSFER; HYDROGEN BONDINGS; HYDROPEROXIDE; HYDROPEROXIDES; METHIONINE RESIDUES; METHIONINE SULFOXIDE; N-TERMINAL; OXIDIZING POTENTIALS; OXYGEN TRANSFER; OXYGEN TRANSFER MECHANISM; POTENTIAL MECHANISM; RADICAL ADDITION; SUPEROXIDE; TYROSYL RADICALS;

AMINATION; AMINO ACIDS; FREE RADICAL REACTIONS; HYDROGEN; HYDROGEN BONDS; ORGANIC COMPOUNDS; OXYGEN; PEPTIDES; RATE CONSTANTS;

AMINES;

HYDROPEROXIDE DERIVATIVE; METHIONINE; METHIONINE SULFOXIDE; OXYGEN; PEROXIDASE; SUPEROXIDE; TYROSINE; TYROSINE HYDROPEROXIDE; UNCLASSIFIED DRUG; AMINE; DRUG DERIVATIVE; HYDROGEN PEROXIDE; PEPTIDE; SINGLET OXYGEN;

ADDITION REACTION; AMINO TERMINAL SEQUENCE; ARTICLE; CONTROLLED STUDY; CYCLIZATION; ELECTRON TRANSPORT; HYDROGEN BOND; OXIDATION REDUCTION POTENTIAL; OXYGEN TRANSPORT; PRIORITY JOURNAL; AMINO ACID SEQUENCE; CHEMISTRY; DIMERIZATION; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLISM; MOLECULAR GENETICS;

AMINES; AMINO ACID SEQUENCE; CHROMATOGRAPHY, LIQUID; DIMERIZATION; HYDROGEN PEROXIDE; MASS SPECTROMETRY; METHIONINE; MOLECULAR SEQUENCE DATA; OXYGEN; PEPTIDES; SINGLET OXYGEN; SUPEROXIDES; TYROSINE;

EID: 67649354633     PISSN: 00219258     EISSN: 1083351X     Source Type: Journal    
DOI: 10.1074/jbc.M809396200     Document Type: Article

References (36)

1. Imlay, J. A. (2008) Annu. Rev. Biochem. 77, 755-776
2. Winterbourn, C. C. (2008) Nat. Chem. Biol. 4, 278-286
3. Liochev, S. I., and Fridovich, I. (1999) IUBMB Life 48, 157-161
4. Beckman, J. S., and Koppenol, W. H. (1996) Am. J. Physiol. 271, C1424-C1437
5. Winterbourn, C. C., Parsons-Mair, H. N., Gebicki, S., Gebicki, J. M., and Davies, M. J. (2004) Biochem. J. 381, 241-248
6. Winterbourn, C. C., and Kettle, A. J. (2003) Biochem. Biophys. Res. Commun. 305, 729-736
7. Jin, F., Leitich, J., and von Sonntag, C. (1993) J. Chem. Soc. Perkin Trans. II, 1583-1588
8. Davies, M. J. (2005) Biochim. Biophys. Acta 1703, 93-109
9. Dean, R. T., Fu, S. L., Stocker, R., and Davies, M. J. (1997) Biochem. J. 324, 1-18
10. Bobrowski, K., Wierzchowski, K. L., Holcman, J., and Ciurak, M. (1990) Int. J. Radiat. Biol. 57, 919-932
11. Garrison, W. M. (1987) Chem. Rev. 87, 381-398
12. Prutz, W. A., Siebert, F., Butler, J., Land, E. J., Menez, A., and Montenaygarestier, T. (1982) Biochim. Biophys. Acta 705, 139-149
13. Zhang, H., Zielonka, J., Sikora, A., Joseph, J., Xu, Y., and Kalyanaraman, B. (2008) Arch. Biochem. Biophys. 10.1016/ j.abb.2008.11.018
14. Stubbe, J. A., and van der Donk, W. A. (1998) Chem. Rev. 98, 705-762
15. Beal, M. F. (2002) Free Radic. Biol. Med. 32, 797-803
16. Heinecke, J. W., Li, W., Francis, G. A., and Goldstein, J. A. (1993) J. Clin. Investig. 91, 2866-2872
17. Souza, J. M., Peluffo, G., and Radi, R. (2008) Free Radic. Biol. Med. 45, 357-366
18. d'Allesandro, N., Bianchi, G., Fang, X., Jin, F., Schuchmann, H.-P., and von Sonntag, C. (2000) J. Chem. Soc. Perkin Trans. II, 1862-1867
19. Jonsson, M., Lind, T., Reitberger, T. E., Eriksen, T. E., and Merenyi, G. (1993) J. Phys. Chem. 97, 8229-8233
20. Mozziconacci, O., Mirkowski, J., Rusconi, F., Pernot, P., Bobrowski, K., and Houee-Levin, C. (2007) Free Radic. Biol. Med. 43, 229-240
21. Stadtman, E. R., and Levine, R. L. (2003) Amino Acids 25, 207-218
22. Moskovitz, J., Flescher, E., Berlett, B. S., Azare, J., Poston, J. M., and Stadtman, E. R. (1998) Proc. Natl. Acad. Sci. U. S. A. 95, 14071-14075
23. Wright, A., Bubb, W. A., Hawkins, C. L., and Davies, M. J. (2002) Photochem. Photobiol. 76, 35-46
24. Wolff, S. P. (1994) Methods Enzymol. 233, 182-189
25. Gieseg, S. P., Simpson, J. A., Charlton, T. S., Duncan, M. W., and Dean, R. T. (1993) Biochemistry 32, 4780-4786
26. Winterbourn, C. C., Pichorner, H., and Kettle, A. J. (1997) Arch. Biochem. Biophys. 338, 15-21
27. Pichorner, H., Metodiewa, D., and Winterbourn, C. C. (1995) Arch. Biochem. Biophys. 323, 429-437
28. Jiang, X. Y., Smith, J. B., and Abraham, E. C. (1996) J. Mass Spectrom. 31, 1309-1310
29. Miyamoto, S., Martinez, G. R., Rettori, D., Augusto, O., Medeiros, M. H. G., and Di Mascio, P. (2006) Proc. Natl. Acad. Sci. U. S. A. 103, 293-298
30. Saito, I., Chujo, Y., Shimazu, H., Yamane, M., Matsuura, T., and Cahnmann, H. J. (1975) J. Am. Chem. Soc. 97, 5272-5277
31. Villamena, F. A., Xia, S., Merle, J. K., Lauricella, R., Tuccio, B., Hadad, C. M., and Zweier, J. L. (2007) J. Am. Chem. Soc. 129, 8177-8191
32. Ohkubo, K., Kitaguchi, H., and Fukuzumi, S. (2006) J. Phys. Chem. A 110, 11613-11616
33. Field, S. M., and Villamena, F. A. (2008) Chem. Res. Toxicol. 21, 1923-1932
34. Bruice, T. C. (1976) Annu. Rev. Biochem. 45, 331-373
35. Garner, B., Witting, P. K., Waldeck, A. R., Christison, J. K., Raftery, M., and Stocker, P. (1998) J. Biol. Chem. 273, 6080-6087
36. Garner, B., Waldeck, A. R., Witting, P. K., Rye, K. A., and Stocker, P. (1998) J. Biol. Chem. 273, 6088-6095