Mass spectrometric identification of oxidative modifications of tryptophan residues in proteins: Chemical artifact or post-translational modification?

Journal of the American Society for Mass Spectrometry

Volumn 21, Issue 7, 2010, Pages 1114-1117

  Perdivara, Irina ^a,b   Deterding, Leesa J ^a   Przybylski, Michael ^b   Tomer, Kenneth B ^a  

^a NATIONAL INSTITUTE OF ENVIRONMENTAL HEALTH SCIENCES   (United States)

^b UNIVERSITY OF KONSTANZ   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTROPHORETIC SEPARATIONS; GEL ELECTROPHORESIS; HEAVY AND LIGHT CHAINS; INGEL DIGESTION; LIQUID CHROMATOGRAPHY-TANDEM MASS SPECTROMETRY; MASS SPECTROMETRIC IDENTIFICATION; MITOCHONDRIAL PROTEIN; OXIDATIVE MODIFICATION; PEPTIDE MASS FINGERPRINTING; POST-TRANSLATIONAL MODIFICATIONS; REDOX METABOLISM; SAMPLE HANDLING; SDS-PAGE; TRYPTOPHAN OXIDATION; TRYPTOPHAN RESIDUES;

AMINO ACIDS; ANTIBODIES; ELECTROPHORESIS; GELS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; OXIDATION; UNCERTAINTY ANALYSIS;

CHEMICAL MODIFICATION;

TRYPTOPHAN;

ALKYLATION; AMINO ACID SEQUENCE; ARTICLE; DNA FINGERPRINTING; ELECTROSPRAY MASS SPECTROMETRY; GENETIC HETEROGENEITY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NONHUMAN; OXIDATION; OXIDATIVE STRESS; POLYACRYLAMIDE GEL ELECTROPHORESIS; PROTEIN DEGRADATION; PROTEIN MODIFICATION; PROTEIN PROCESSING; PROTEIN PURIFICATION; TANDEM MASS SPECTROMETRY;

AMINO ACID SEQUENCE; ANIMALS; ANTIBODIES, MONOCLONAL; ARTIFACTS; CHROMATOGRAPHY, LIQUID; DITHIOTHREITOL; ELECTROPHORESIS, POLYACRYLAMIDE GEL; HUMANS; KYNURENINE; MICE; MOLECULAR SEQUENCE DATA; OXIDATION-REDUCTION; PEPTIDE MAPPING; PROTEIN PROCESSING, POST-TRANSLATIONAL; PROTEOMICS; TANDEM MASS SPECTROMETRY; TRYPSIN; TRYPTOPHAN;

EID: 77953911347     PISSN: 10440305     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jasms.2010.02.016     Document Type: Article

References (23)

1. Alvarez B., Radi R. Peroxynitrite Reactivity with Amino Acids and Proteins. Amino Acids 2003, 25(3-4):295-311.
2. Davies M.J., Truscott R.J. Photo-Oxidation of Proteins and Its Role in Cataractogenesis. J. Photochem. Photobiol. B 2001, 63(1-3):114-125.
3. Takamoto K., Chance M.R. Radiolytic Protein Footprinting with Mass Spectrometry to Probe the Structure of Macromolecular complexes. Annu. Rev. Biophys. Biomol. Struct. 2006, 35:251-276.
4. Bregere C., Rebrin I., Sohal R.S. Detection and Characterization of In Vivo Nitration and Oxidation of Tryptophan rResidues in Proteins. Methods Enzymol. 2008, 441:339-349.
5. Froelich J.M., Reid G.E. The Origin and Control of Ex Vivo Oxidative Peptide Modifications Prior to Mass Spectrometry Analysis. Proteomics 2008, 8(7):1334-1345.
6. Taylor S.W., Fahy E., Murray J., Capaldi R.A., Ghosh S.S. Oxidative Post-Translational Modification of Tryptophan Residues in Cardiac Mitochondrial Proteins. J. Biol. Chem. 2003, 278(22):19587-19590.
7. Moller I.M., Kristensen B.K. Protein Oxidation in Plant Mitochondria Detected as Oxidized Tryptophan. Free Radic. Biol. Med. 2006, 40(3):430-435.
8. Hains P.G., Truscott R.J. Post-Translational Modifications in the Nuclear Region of Young, Aged, and Cataract Human Lenses. J. Proteome Res. 2007, 6(10):3935-3943.
9. MacCoss M.J., McDonald W.H., Saraf A., Sadygov R., Clark J.M., Tasto J.J., Gould K.L., Wolters D., Washburn M., Weiss A., Clark J.I., Yates J.R. Shotgun Identification of Protein Modifications from Protein Complexes and Lens Tissue. Proc. Natl. Acad. Sci. U.S.A. 2002, 99(12):7900-7905.
10. Kunz L., Zeidler U., Haegele K., Przybylski M., Stark G. Photodynamic and Radiolytic Inactivation of Ion Channels Formed by Gramicidin A: Oxidation and Fragmentation. Biochemistry 1995, 34(37):11895-11903.
11. Obama T., Kato R., Masuda Y., Takahashi K., Aiuchi T., Itabe H. Analysis of Modified Apolipoprotein B-100 Structures Formed in Oxidized Low-Density Lipoprotein Using LC-MS/MS. Proteomics 2007, 7(13):2132-2141.
12. Thiede B., Lamer S., Mattow J., Siejak F., Dimmler C., Rudel T., Jungblut P.R. Analysis of Missed Cleavage Sites, Tryptophan Oxidation, and N-Terminal Pyroglutamylation After In-Gel Tryptic Digestion. Rapid Commun. Mass Spectrom. 2000, 14(6):496-502.
13. Staniszewska M., Nagaraj R.H. Detection of Kynurenine Modifications in Proteins Using a Monoclonal Antibody. J. Immunol. Methods 2007, 324(1-2):63-73.
14. Zhang X., Shi L., Shu S., Wang Y., Zhao K., Xu N., Liu S., Roepstorff P. An Improved Method of Sample Preparation on AnchorChip Targets for MALDI-MS and MS/MS and Its Application in the Liver Proteome Project. Proteomics 2007, 7(14):2340-2349.
15. Bienvenut W.V., Deon C., Pasquarello C., Campbell J.M., Sanchez J.C., Vestal M.L., Hochstrasser D.F. Matrix-Assisted Laser Desorption/Ionization-Tandem Mass Spectrometry with High Resolution and Sensitivity for Identification and Characterization of Proteins. Proteomics 2002, 2(7):868-876.
16. Karty J.A., Ireland M.M., Brun Y.V., Reilly J.P. Artifacts and Unassigned Masses Encountered in Peptide Mass Mapping. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 2002, 782(1-2):363-383.
17. Lemma-Gray P., Weintraub S.T., Carroll C.A., Musatov A., Robinson N.C. Tryptophan 334 Oxidation in Bovine Cytochrome c Oxidase Subunit I Involves Free Radical Migration. FEBS Lett. 2007, 581(3):437-442.
18. Yang J., Wang S., Liu J., Raghani A. Determination of Tryptophan Oxidation of Monoclonal Antibody by Reversed Phase High Performance Liquid Chromatography. J. Chromatogr. A 2007, 1156(1-2):174-182.
19. Perdivara I., Deterding L., Moise A., Tomer K.B., Przybylski M. Determination of Primary Structure and Microheterogeneity of a β-Amyloid Plaque-Specific Antibody Using High-Performance LC-Tandem Mass Spectrometry. Anal. Bioanal. Chem. 2008, 391(1):325-336.
20. Yamakura F., Matsumoto T., Ikeda K., Taka H., Fujimura T., Murayama K., Watanabe E., Tamaki M., Imai T., Takamori K. Nitrated and Oxidized Products of a Single Tryptophan Residue in Human Cu, Zn-Superoxide Dismutase Treated with Either Peroxynitrite-Carbon Dioxide or Myeloperoxidase-Hydrogen Peroxide-Nitrite. J. Biochem. 2005, 138(1):57-69.
21. Swiderek K.M., Davis M.T., Lee T.D. The Identification of Peptide Modifications Derived from Gel-Separated Proteins Using Electrospray Triple Quadrupole and Ion Trap Analyses. Electrophoresis 1998, 19(6):989-997.
22. Chen M., Cook K.D. Oxidation Artifacts in the Electrospray Mass Spectrometry of A-β Peptide. Anal. Chem. 2007, 79(5):2031-2036.
23. Cohen S.L. Ozone in Ambient Air as a Source of Adventitious Oxidation. A Mass Spectrometric Study. Anal. Chem. 2006, 78(13):4352-4362.