Superoxide reaction with tyrosyl radicals generates para -hydroperoxy and para-hydroxy derivatives of tyrosine

Journal of the American Chemical Society

Volumn 134, Issue 40, 2012, Pages 16773-16780

  Möller, Matías N ^a,b   Hatch, Duane M ^a   Kim, Hye Young H ^a   Porter, Ned A ^a  

^a VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b UNIVERSIDAD DE LA REPÚBLICA   (Uruguay)

Author keywords

[No Author keywords available]

Indexed keywords

CONJUGATE ADDITION; DIFFUSION-LIMITED REACTIONS; FENTON CONDITIONS; FREE AMINES; HORSE-RADISH PEROXIDASE; HYDROPEROXIDES; HYDROXYL RADICALS; L-ALANINE; N-TERMINALS; OXIDIZING SPECIES; RP-HPLC; SUPEROXIDES; TYROSINE OXIDATION; TYROSYL RADICALS; XANTHINE OXIDASE;

CARBOXYLIC ACIDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXYGEN; PEPTIDES;

AMINO ACIDS;

3 ( 1 HYDROPEROXY 4 OXOCYCLOHEXA 2,5 DIEN 1 YL) LEVO ALANINE; 3A HYDROXYPEROXY 6 OXO 2,3,3A,6,7,7A HEXAHYDRO 1H INDOLE 2 CARBOXYLIC ACID; 4 ALCOHOL; ALANINE DERIVATIVE; ALCOHOL DERIVATIVE; AMINE; AMINO TERMINAL TELOPEPTIDE; CARBOXYLIC ACID DERIVATIVE; CYCLOHEXADIENONE; CYCLOHEXANE DERIVATIVE; GLYCYLTYROSINE; HORSERADISH PEROXIDASE; HYDROPEROXIDE DERIVATIVE; HYDROXYL GROUP; HYDROXYL RADICAL; LEUCINE ENKEPHALIN; PEPTIDE; RADICAL; SUPEROXIDE; TYROSINE; TYROSINE DERIVATIVE; TYROSYLGLYCINE; UNCLASSIFIED DRUG; XANTHINE OXIDASE;

AMINO TERMINAL SEQUENCE; ANIMAL CELL; ARTICLE; CONJUGATION; CONTROLLED STUDY; FENTON REACTION; LIQUID CHROMATOGRAPHY TANDEM MASS SPECTROMETRY; MOLECULAR STABILITY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION REDUCTION REACTION; RADICAL REACTION; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; TANDEM MASS SPECTROMETRY;

ANIMALS; ARMORACIA; CATTLE; ENKEPHALIN, LEUCINE; HORSERADISH PEROXIDASE; HYDROGEN PEROXIDE; MODELS, MOLECULAR; OXIDATION-REDUCTION; PEPTIDES; SUPEROXIDE DISMUTASE; SUPEROXIDES; TYROSINE; XANTHINE OXIDASE;

EID: 84867346147     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja307215z     Document Type: Article

References (44)

1. Radi, R. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 4003
2. Ischiropoulos, H. Arch. Biochem. Biophys. 1998, 356, 1
3. Ischiropoulos, H. Arch. Biochem. Biophys. 2009, 484, 117
4. Shao, B.; Oda, M. N.; Oram, J. F.; Heinecke, J. W. Chem. Res. Toxicol. 2010, 23, 447
5. Pennathur, S.; Wagner, J. D.; Leeuwenburgh, C.; Litwak, K. N.; Heinecke, J. W. J. Clin. Invest. 2001, 107, 853
6. Zhang, X.; Monroe, M. E.; Chen, B.; Chin, M. H.; Heibeck, T. H.; Schepmoes, A. A.; Yang, F.; Petritis, B. O.; Camp, D. G., 2nd; Pounds, J. G.; Jacobs, J. M.; Smith, D. J.; Bigelow, D. J.; Smith, R. D.; Qian, W. J. Mol. Cell. Proteomics 2010, 9, 1199
7. Fu, S.; Davies, M. J.; Stocker, R.; Dean, R. T. Biochem. J. 1998, 333 (Pt 3) 519
8. Shchepin, R.; Möller, M. N.; Kim, H. Y.; Hatch, D. M.; Bartesaghi, S.; Kalyanaraman, B.; Radi, R.; Porter, N. A. J. Am. Chem. Soc. 2010, 132, 17490
9. Wright, A.; Bubb, W. A.; Hawkins, C. L.; Davies, M. J. Photochem. Photobiol. 2002, 76, 35
10. Jin, F.; Leitich, J.; von Sonntag, C. J. Photochem. Photobiol A 1995, 92, 147
11. Jin, F.; Leitich, J.; von Sonntag, C. J. Chem. Soc., Perkin Trans. 1993, 2, 1583
12. Nagy, P.; Kettle, A. J.; Winterbourn, C. C. J. Biol. Chem. 2009, 284, 14723
13. Winterbourn, C. C.; Parsons-Mair, H. N.; Gebicki, S.; Gebicki, J. M.; Davies, M. J. Biochem. J. 2004, 381, 241
14. Nagy, P.; Kettle, A. J.; Winterbourn, C. C. Free Radical Biol. Med. 2010, 49, 792
15. Das, A. B.; Nagy, P.; Abbott, H. F.; Winterbourn, C. C.; Kettle, A. J. Free Radical Biol. Med. 2010, 48, 1540
16. Mozziconacci, O.; Mirkowski, J.; Rusconi, F.; Pernot, P.; Bobrowski, K.; Houee-Levin, C. Free Radical Biol. Med. 2007, 43, 229
17. Field, S. M.; Villamena, F. A. Chem. Res. Toxicol. 2008, 21, 1923
18. Nagy, P.; Lechte, T. P.; Das, A. B.; Winterbourn, C. C. J. Biol. Chem. 2012, 287, 26068
19. Edelhoch, H. Biochemistry 1967, 6, 1948
20. Marumo, K.; Waite, J. H. Biochim. Biophys. Acta 1986, 872, 98
21. Buettner, G. R. Arch. Biochem. Biophys. 1993, 300, 535
22. Folkes, L. K.; Trujillo, M.; Bartesaghi, S.; Radi, R.; Wardman, P. Arch. Biochem. Biophys. 2011, 506, 242
23. Steinmann, D.; Ji, J. A.; Wang, Y. J.; Schoneich, C. Mol. Pharm. 2012, 9, 803
24. Guzik, T. J.; Mussa, S.; Gastaldi, D.; Sadowski, J.; Ratnatunga, C.; Pillai, R.; Channon, K. M. Circulation 2002, 105, 1656
25. Kelkar, A.; Kuo, A.; Frishman, W. H. Cardiol. Rev. 2011, 19, 265
26. Dikalov, S. Free Radical Biol. Med. 2011, 51, 1289
27. Augusto, O.; Bonini, M. G.; Amanso, A. M.; Linares, E.; Santos, C. C.; De Menezes, S. L. Free Radical Biol. Med. 2002, 32, 841
28. Heinecke, J. W.; Li, W.; Francis, G. A.; Goldstein, J. A. J. Clin. Invest. 1993, 91, 2866
29. Heinecke, J. W.; Li, W.; Daehnke, H. L., III; Goldstein, J. A. J. Biol. Chem. 1993, 268, 4069
30. DiMarco, T.; Giulivi, C. Mass Spectrom. Rev. 2007, 26, 108
31. Pennathur, S.; Bergt, C.; Shao, B.; Byun, J.; Kassim, S. Y.; Singh, P.; Green, P. S.; McDonald, T. O.; Brunzell, J.; Chait, A.; Oram, J. F.; O'Brien, K.; Geary, R. L.; Heinecke, J. W. J. Biol. Chem. 2004, 279, 42977
32. Lancaster, J. R., Jr. Chem. Res. Toxicol. 2006, 19, 1160
33. Lynn, K.; Purdie, J. Int. J. Radiat. Phys. Chem. 1976, 8, 685
34. Boguta, G.; Dancewicz, A. Int. J. Radiat. Biol. 1981, 39, 163
35. Getoff, N. Amino Acids 1992, 2, 195
36. Maskos, Z.; Rush, J. D.; Koppenol, W. H. Arch. Biochem. Biophys. 1992, 296, 521
37. Solar, S.; Solar, W.; Getoff, N. J. Phys. Chem. 1984, 88, 2091
38. Schuler, R. H.; Albarran, G.; Zajicek, J.; George, M. V.; Fessenden, R. W.; Carmichael, I. J. Phys. Chem. A 2002, 106, 12178
39. Albarran, G.; Schuler, R. H. J. Phys. Chem. A 2005, 109, 9363
40. Lee, S.; Chen, Y.; Luo, H.; Wu, A. A.; Wilde, M.; Schumacker, P. T.; Zhao, Y. J. Proteome Res. 2010, 9, 5705
41. Jacobs, A. T.; Marnett, L. J. Acc. Chem. Res. 2010, 43, 673
42. Iles, K. E.; Dickinson, D. A.; Wigley, A. F.; Welty, N. E.; Blank, V.; Forman, H. J. Free Radical Biol. Med. 2005, 39, 355
43. Giasson, B. I.; Duda, J. E.; Murray, I. V.; Chen, Q.; Souza, J. M.; Hurtig, H. I.; Ischiropoulos, H.; Trojanowski, J. Q.; Lee, V. M. Science 2000, 290, 985
44. Stefani, M.; Dobson, C. M. J. Mol. Med. (Berl) 2003, 81, 678