Isolation and analysis of dityrosine from enzyme-catalyzed oxidation of tyrosine and X-irradiated peptide and proteins

Chemico-Biological Interactions

Volumn 108, Issue 3, 1998, Pages 171-185

  Sharma, Minoti ^a   Jain, Rama ^a  

^a ROSWELL PARK CANCER INSTITUTE   (United States)

Author keywords

Dansylated DT; Fluorescence labeling; Radiation induced DT; Reversed phase HPLC; X irradiated peptide; X irradiated protein

Indexed keywords

AMINO ACID; DANSYL CHLORIDE; ENZYME; FLUORESCENT DYE; N ACETYLTYROSINE; NITROGEN; PEPTIDE; PROTEIN; RIBONUCLEASE A; TRIPEPTIDE; TYROSINE;

ANALYSIS; ARTICLE; FLUORESCENCE; ISOLATION AND PURIFICATION; OXIDATION; OXIDATIVE STRESS; PROTON NUCLEAR MAGNETIC RESONANCE; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; X IRRADIATION;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DANSYL COMPOUNDS; FLUORESCENCE; HYDROLYSIS; MAGNETIC RESONANCE SPECTROSCOPY; OLIGOPEPTIDES; OXIDATION-REDUCTION; RIBONUCLEASE, PANCREATIC; SERUM ALBUMIN, BOVINE; TYROSINE;

EID: 0032579208     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0009-2797(97)00098-7     Document Type: Article

References (31)

1. Stadtman E.R. Oxidation of free amino acids and amino acid residues in proteins by radiolysis and by metal-catalyzed reactions. Ann. Rev. Biochem. 62:1993;797-821.
2. Stadtman E.R. Role of oxidized amino acids in protein breakdown and stability. Methods Enzymol. 258:1995;379-393.
3. Levine R.L., Garland D., Oliver C.N., Amici A., Climent I., Lenz A.-G., Ahn B.-W., Shaltiel S., Stadtman E.R. Determination of carbonyl content in oxidatively modified proteins. Methods Enzymol. 186:1990;464-478.
4. Levine R.L., Williams J.A., Stadtman E.R., Shacter E. Carbonyl assays for determination of oxidatively modified proteins. Methods Enzymol. 233:1994;346-357.
5. Huggins T.G., Wells-Knecht M.C., Detorie N.A., Baynes J.W., Thorpe S.R. Formation of o-tyrosine and dityrosine in proteins during radiolytic and metal-catalyzed oxidation. J. Biol. Chem. 268:1993;12341-12347.
6. Cao G., Culter R.G. Difficulties in measuring reactive protein carbonyls in tissues using 2,4-dinitrophenylhydrazines. Arch. Biochem. Biophys. 320:1995;106-114.
7. Garrison W.M. Reaction mechanisms in the radiolysis of peptides, polypeptides, and proteins. Chem. Rev. 87:1987;381-398.
8. Alexander P., Rosen D. A comparison of the effects of x-rays and alpha rays on some proteins and amino acids in dilute aqueous solution. Radiat. Res. 15:1961;475-488.
9. Fletcher G.L., Okada S. Radiation-induced formation of dihydroxyphenylalanine from tyrosine and tyrosine-containing peptides in aqueous solution. Radiat. Res. 15:1961;349-354.
10. Rowbottom J. The radiolysis of aqueous solutions of tyrosine. J. Biol. Chem. 212:1955;877-885.
11. Vermeil C., Lefort M. Production de tyrosine par action des rayons g surles solutions aqueuses de phenylalanine. C. R. Acad. Sci. Paris. 244:1955;889-891.
12. Farber J.M., Levine R.L. Sequence of a peptide susceptible to mixed-function oxidation. J. Biol. Chem. 261:1986;4574-4578.
13. Uchida K., Kawakishi S. Ascorbate-mediated specific oxidation of the imidazole ring in a histidine derivative. Bioorg. Chem. 17:1989;330-343.
14. Davies K.J.A., Delsignore M.E., Lin S.W. Protein damage and degradation by oxygen radicals. J. Biol. Chem. 262:1987;9902-9907.
15. Guptasarma P., Balasubramanian D. Hydroxyl radical mediated damage to proteins, with special reference to the crystallins. Biochemistry. 31:1992;4296-4303.
16. Sen A.C., Ueno N., Chakrabarti B. Studies on human lens: origin and development of fluorescent pigments. Photochem. Photobiol. 55:1992;753-764.
17. Wells-Knecht M.C., Huggins T.G., Dyer D.G., Thorpe S.R., Baynes J.W. Oxidized amino acids in lens proteins with age. J. Biol. Chem. 268:1993;12348-12352.
18. Malencik D.A., Zhizhuang Z., Anderson S.R. Determination of dityrosine, phosphotyrosine, phosphothreonine, and phosphoserine by high performance liquid chromatography. Anal. Biochem. 184:1990;353-359.
19. K.J.A. Davies, Biological and medical aspects. Detection of peptidyl-3,4-dihydroxyphenylalanine by amino acid analysis and microsequencing techniques, in: K.J.A. Davies (Ed.), Oxidative Damage and Repair: Chemical, Pergamon, Oxford, 1991.
20. Jain R., Freund H.G., Budzinsky E., Sharma M. Radiation-induced formation of 3,4-dihydroxy phenylalanine in tyrosine-containing peptide and proteins as a function of X-irradiation dose. Bioconjugate Chem. 8:1997;173-178.
21. Aeschbach R., Amado R., Neukom H. Formation of dityrosine cross-links in proteins by oxidation residues. Biochim. Biophys. Acta. 439:1976;292-301.
22. Tapuhi Y., Schmidt D.E., Linder W., Krager B.L. Dansylation of amino acids for high-performance liquid chromatography analysis. Anal. Biochem. 115:1981;123-129.
23. Oray B., Lu H.S., Gracy R.W. High-performance liquid chromatographic separation of Dns-amino acid derivatives and applications to peptide and protein structural studies. J. Chromatogr. 270:1983;253-266.
24. Malencik D.A., Sprouse J.F., Swanson C.A., Anderson S.R. Dityrosine: preparation, isolation, and analysis. Anal. Biochem. 242:1996;202-213.
25. Boguta G., Dancewicz A.M. Radiolytic and enzymatic dimerization of tyrosyl residues in insulin, ribonuclease, papain and collagen. Int. J. Radiat. Biol. 43:1983;249-265.
26. Giulivi C., Davies K.J.A. Dityrosine and tyrosine oxidation products are endogenous markers for the selective proteolysis of oxidatively modified red blood cell hemoglobin by the (the 19 S) Proteasome. J. Biol. Chem. 268:1993;8752-8759.
27. Marquez F.J., Quesada A.R., Sanchez-Jimenez F., Nimez De Castro I. Determination of 27 dansyl amino acid derivatives in biological fluids by reversed-phase high-performance liquid chromatography. J. Chromatogr. 380:1986;275-283.
28. R.P. Haugland, Handbook of Fluorescent Probes and Research Chemicals, Molecular Probes, 6th edn., M.T.Z. Spencer (Ed.), I.D. Johnson, TIC, 1996, p. 41.
29. Tapuhi Y., Miller N., Krager B.L. Practical considerations in the chiral separation of Dns-amino acids by reversed-phase liquid chromatography using metal chelate additives. J. Chromatogr. 205:1981;325-337.
30. Reitsma B.H., Yeung E.S. Optical activity and ultraviolet absorbance detection of dansyl l-amino acids separated by gradient liquid chromatography. Anal. Chem. 59:1987;1059-1061.
31. M. Sharma, H.G. Freund, Development of laser-induced fluorescence detection to assay DNA damage in: B.L. Fearey (Ed.), Optical Methods for Ultrasensitive Detection and Analysis: Techniques and Applications Proc. SPIE 1435, SPIE, Bellingham, WA, pp. 280-291.