The Effect of Histidine Oxidation on the Dissociation Patterns of Peptide Ions

Journal of the American Society for Mass Spectrometry

Volumn 18, Issue 3, 2007, Pages 553-562

  Bridgewater, Juma D ^a   Srikanth, R ^a   Lim, Jihyeon ^a   Vachet, Richard W ^a  

^a UNIVERSITY OF MASSACHUSETTS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYSTEINE; HISTIDINE OXIDATION; METHIONINE; PEPTIDE IONS;

CHEMICAL BONDS; DISSOCIATION; ISOMERS; MASS SPECTROMETRY; OXIDATION; PROTEINS;

AMINO ACIDS;

ACID; BASE; BENZOIC ACID DERIVATIVE; CYSTEINE; HISTIDINE; IMIDAZOLE DERIVATIVE; METHIONINE; PEPTIDE DERIVATIVE; SULFOBENZOIC ACID; UNCLASSIFIED DRUG;

AMINO ACID ANALYSIS; AMINO TERMINAL SEQUENCE; ARTICLE; CARBOXY TERMINAL SEQUENCE; DISSOCIATION; LIQUID CHROMATOGRAPHY; OXIDATION; TANDEM MASS SPECTROMETRY;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HISTIDINE; IONS; MASS SPECTROMETRY; MODELS, CHEMICAL; MODELS, MOLECULAR; OXIDATION-REDUCTION; PEPTIDES; TANDEM MASS SPECTROMETRY;

EID: 33847019913     PISSN: 10440305     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jasms.2006.11.001     Document Type: Article

References (48)

1. Maleknia S.D., Brenowitz M., and Chance M.R. Millisecond Radiolytic Modification of Peptides by Synchrotron X-rays Identified by Mass Spectrometry. Anal. Chem. 71 (1999) 3965-3973
2. Maleknia S.D., Chance M.R., and Downard K.M. Electrospray-assisted Modification of Proteins: A Radical Probe of Protein Structure. Rapid Commun. Mass Spectrom. 13 (1999) 2352-2358
3. Kiselar J.G., Maleknia S.D., Sullivan M., Downard K.M., and Chance M.R. Hydroxyl Radical Probe of Protein Surfaces Using Synchrotron X-ray Radiolysis and Mass Spectrometry. Int. J. Radiat. Biol. 78 (2002) 101-114
4. Guan J., Vorobiev S., Almo S.C., and Chance M.R. Mapping the G-Actin Binding Surface of Cofilin Using Synchrotron Protein Footprinting. Biochemistry 41 (2002) 5765-5775
5. 2+-Dependent Activation of Gelsolin by Using Synchrotron Footprinting. Proc. Natl. Acad. Sci. U.S.A. 100 (2003) 3942-3947
6. Wong J.W., Maleknia S.D., and Downard K.M. Study of the Ribonuclease-S-Protein-Peptide Complex Using a Radical Probe and Electrospray Ionization Mass Spectrometry. Anal. Chem. 75 (2003) 1557-1563
7. Sharp J.S., Becker J.M., and Hettich R.L. Protein Surface Mapping by Chemical Oxidation: Structural Analysis by Mass Spectrometry. Anal. Biochem. 313 (2003) 216-225
8. Sharp J.S., Becker J.M., and Hettich R.L. Analysis of Protein Solvent Accessible Surfaces by Photochemical Oxidation and Mass Spectrometry. Anal. Chem. 76 (2004) 672-683
9. Guan J.Q., and Chance M.R. Structural Proteomics of Macromolecular Assemblies Using Oxidative Footprinting and Mass Spectrometry. Trends Biochem. Sci. 30 (2005) 583-592
10. Hambly D.M., and Gross M.L. Laser Flash Photolysis of Hydrogen Peroxide to Oxidize Protein Solvent-Accessible Residues on the Microsecond Timescale. J. Am. Soc. Mass Spectrom. 16 (2005) 2057-2063
11. 2-Treated Cu,Zn-SOD Protein with LC-ESI-Q-TOF-MS, MS/MS for the Determination of the Copper-Binding Site. J. Am. Chem. Soc. 123 (2001) 9268-9278
12. Hovorka S.W., Williams T.D., and Schöneich C. Characterization of the Metal-Binding Site of Bovine Growth Hormone through Site-Specific metal Catalyzed Oxidation and High-Performance Liquid Chromatography-Tandem Mass Spectrometry. Anal. Biochem. 300 (2002) 206-211
13. Schöneich C., and Williams T.D. Cu(II)-Catalyzed Oxidation of β-Amyloid Peptide Targets His13 and His14 over His6: Detection of 2-Oxo-histidine by HPLC-MS/MS. Chem. Res. Toxicol. 15 (2002) 717-722
14. Lim J., and Vachet R.W. Development of a Methodology Based on Metal-Catalyzed Oxidation Reactions and Mass Spectrometry to Determine the Metal Binding Sites in Copper Metalloproteins. Anal. Chem. 75 (2003) 1164-1172
15. Lim J., and Vachet R.W. Using Mass Spectrometry to Study Copper-Protein Binding Under Native and Non-Native Conditions: β-2-Microglobulin. Anal. Chem. 76 (2004) 3498-3504
16. Bridgewater J.D., and Vachet R.W. Metal-Catalyzed Oxidation Reactions and Mass Spectrometry: The Roles of Ascorbate and Different Oxidizing Agents in Determining Cu-Protein-Binding Sites. Anal. Biochem. 41 (2005) 122-130
17. Bridgewater J.D., and Vachet R.W. Using Microwave-Assisted Metal-Catalyzed Oxidation Reactions and Mass Spectrometry to Increase the Rate at Which the Copper-Binding Sites of a Protein Are Determined. Anal. Chem. 77 (2005) 4649-4653
18. Bridgewater J.D., Lim J., and Vachet R.W. Transition Metal-Peptide Binding Studied by Metal-Catalyzed Oxidation Reactions and Mass Spectrometry. Anal. Chem. 78 (2006) 2432-2438
19. Burlet O., Yang C.-Y., and Gaskell S.J. Influence of Cysteine to Cysteic Acid Oxidation on the Collision-Activated Decomposition of Protonated Peptides: Evidence for Intraionic Interactions. J. Am. Soc. Mass Spectrom. 3 (1992) 337-344
20. Cox K.A., Gaskell S.J., Morris M., and Whiting A. Role of the Site of Protonation in the Low-Energy Decompositions of Gas-Phase Peptide Ions. J. Am. Soc. Mass Spectrom. 7 (1996) 522-531
21. Summerfield S.G., Cox K.A., and Gaskell S.J. The Promotion of. d-Type Ions during the Low Energy Collision-Induced Dissociation of Some Cysteic Acid-Containing Peptides. J. Am. Soc. Mass Spectrom. 8 (1997) 25-31
22. Tsaprailis G., Nair H., Somogyi A., Wysocki V.H., Zhong W., Futrell J.H., Summerfield S.G., and Gaskell S.J. Influence of Secondary Structure on the Fragmentation of Protonated Peptides. J. Am. Chem. Soc. 121 (1999) 5142-5154
23. Wang Y., Vivekananda S., Men L., and Zhang Q. Fragmentation of Protonated Ions of Peptides Containing Cysteine, Cysteine Sulfinic Acid, and Cysteine Sulfonic Acid. J. Am. Soc. Mass Spectrom. 15 (2004) 697-702
24. Men L., and Wang Y. Further Studies on the Fragmentation of Protonated Ions of Peptides Containing Aspartic Acid, Glutamic Acid, Cysteine Sulfinic Acid, and Cysteine Sulfonic Acid. Rapid Commun. Mass Spectrom. 19 (2005) 23-30
25. Jiang X., Smith J.B., and Abraham E.C. Identification of a MS-MS Fragment Diagnostic for Methionine Sulfoxide. J. Mass Spectrom. 31 (1996) 1309-1310
26. Lagerwerf F.M., van de Weert M., Heerma W., and Haverkamp J. Identification of Oxidized Methionine in Peptides. Rapid Commun. Mass Spectrom. 10 (1996) 1905-1910
27. Qin J., and Chait B.T. Identification and Characterization of Posttranslational Modifications of Proteins by MALDI Ion Trap Mass Spectrometry. Anal. Chem. 69 (1997) 4002-4009
28. O'Hair R.A.J., and Reid G.E. Neighboring Group versus cis-Elimination Mechanisms for Side Chain Loss from Protonated Methionine, Methionine Sulfoxide and their Peptides. Eur. Mass Spectrom. 5 (1999) 325-334
29. Reid G.E., Roberts K.D., Kapp E.A., and Simpson R.J. Statistical and Mechanistic Approaches to Understanding the Gas-Phase Fragmentation Behavior of Methionine Sulfoxide Containing Peptides. J. Proteome Res. 3 (2004) 751-759
30. Buxton G.V., Greenstock C.L., Helman W.P., and Ross A.B. Critical Review of Rate Constants for Reactions of Hydrated Electrons, Hydrogen Atoms, and Hydroxyl Radicals in Aqueous Solution. J. Phys. Chem. Ref. Data 17 (1988) 513-886
31. Stadtman E.R., and Berlett B.S. Reactive Oxygen-Mediated Protein Oxidation in Aging and Disease. Chem. Res. Toxicol. 10 (1997) 485-494
32. Schöneich C. Reactive Oxygen Species and Biological Aging: A Mechanistic Approach. Exp. Gerontol. 34 (1999) 19-34
33. Davies M.J. The Oxidative Environment and Protein Damage. Biochim. Biophys. Acta 1703 (2005) 93-109
34. Uchida K., and Kawakishi S. 2-Oxo-Histidine as a Novel Biological Marker for Oxidatively Modified Proteins. FEBS Lett. 332 (1993) 208-210
35. Huang Y., Wysocki V.H., Tabb D.L., and Yates J.R. The Influence of Histidine on Cleavage C-terminal to Acidic Residues in Doubly-Protonated Tryptic Peptides. Int. J. Mass Spectrom. 219 (2002) 233-244
36. Tabb D.L., Smith L.L., Breci L.A., Wysocki V.H., Lin D., and Yates J.R. Statistical Characterization of Ion Trap Tandem Mass Spectra from Doubly Charged Tryptic Peptides. Anal. Chem. 75 (2003) 1155-1163
37. Wysocki V.H., Tsaprailis G., Smith L.L., and Breci L.A. Mobile and Localized Protons: A Framework for Understanding Peptide Dissociation. J. Mass Spectrom. 35 (2000) 1399-1406
38. Farrugia J.M., Taverner T., and O'Hair R.A.J. Side-Chain Involvement in the Fragmentation Reactions of the Protonated Methyl Esters of Histidine and Its Peptides. Int. J. Mass Spectrom. 209 (2001) 99-112
39. 2 Ions have Oxazolone Structures?. Multistage Mass Spectrometry and ab initio Studies on Protonated N-acyl Amino Acid Methyl Ester Model Systems. Int. J. Mass Spectrom 210/211 (2001) 71-87
40. Tsaprailis G., Nair H., Zhong W., Kuppannan K., Futrell J.H., and Wysocki V.H. A Mechanistic Investigation of the Enhanced Cleavage at Histidine in the Gas-Phase Dissociation of Protonated Peptides. Anal. Chem. 76 (2004) 2083-2094
41. Uchida K., and Kawakishi S. Ascorbate-Mediated Specific Oxidation of the Imidazole Ring in a Histidine Derivative. Bioorg. Chem. 17 (1989) 330-343
42. Lewisch S.A., and Levine R.L. Determination of 2-Oxohistidine by Amino Acid Analysis. Anal. Biochem. 231 (1995) 440-446
43. Zhao F., Ghezzo-Schöneich E., Aced G.I., Hong J., Milby T., and Schöneich C. Metal-Catalyzed Oxidation of Histidine in Human Growth Hormone: Mechanism, Isotope Effects, and Inhibition by a Mild Denaturing Alcohol. J. Biol. Chem. 272 (1997) 9019-9029
44. Schöneich C. Mechanisms of Metal-Catalyzed Oxidation of Histidine to 2-Oxo-Histidine in Peptides and Proteins. J. Pharm. Biomed. Anal. 21 (2000) 1093-1097
45. 2+ Insulin to Metal-Catalyzed Oxidation: Detection of 2-Oxo-Histidine by Tandem Mass Spectrometry. Pharm. Res. 19 (2002) 530-537
46. Hunter E.P., and Lias S.G. Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update. J. Phys. Chem. Ref. Data 27 (1998) 413-656
47. Keough T., Youngquist R.S., and Lacey M.P. A Method for High-Sensitivity Peptide Sequencing Using Postsource Decay Matrix-Assisted Laser Desorption Ionization Mass Spectrometry. Proc. Natl. Acad. Sci. U.S.A. 96 (1999) 7131-7136
48. Bauer M.D., Sun Y., Keough T., and Lacey M.P. Sequencing of Sulfonic Acid Derivatized Peptides by Electrospray Mass Spectrometry. Rapid Commun. Mass Spectrom. 14 (2000) 924-929