Fragmentation of α-Radical Cations of Arginine-Containing Peptides

Journal of the American Society for Mass Spectrometry

Volumn 21, Issue 4, 2010, Pages 511-521

  Laskin, Julia ^a   Yang, Zhibo ^a   Ng, C M Dominic ^b   Chu, Ivan K ^b  

^a PACIFIC NORTHWEST NATIONAL LABORATORY   (United States)

^b UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; ARGININE; CARBON; CHAINS; DISSOCIATION; ELECTRONS; POSITIVE IONS;

COLLISION INDUCED DISSOCIATION; DISSOCIATION PRODUCTS; FRAGMENTATION PATHWAYS; GAS-PHASE FRAGMENTATION; HYDROGEN ABSTRACTION; PEPTIDE COMPLEX; PEPTIDE RADICAL CATIONS; RADICAL CATIONS;

PEPTIDES;

ARGININE; CATION; COBALT; ETHYLENEDIAMINE DERIVATIVE; N,N' ETHYLENEBIS(SALICYLIDENEIMINATO); UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; AMINO TERMINAL SEQUENCE; ARTICLE; CHEMICAL BOND; COLLISIONALLY ACTIVATED DISSOCIATION; ELECTRON; PROTEIN ANALYSIS; PROTEIN CLEAVAGE; PROTEIN INTERACTION; PROTEIN STRUCTURE;

EID: 77950337558     PISSN: 10440305     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jasms.2009.12.021     Document Type: Article

References (60)

1. Zubarev R.A., Kelleher N.L., McLafferty F.W. Electron Capture Dissociation of Multiply Charged Protein Cations. A Nonergodic Process. J. Am. Chem. Soc. 1998, 120:3265-3266.
2. Zubarev R.A. Reactions of Polypeptide Ions with Electrons in the Gas Phase. Mass Spectrom. Rev. 2003, 22:57-77.
3. Syka J.E.P., Coon J.J., Schroeder M.J., Shabanowitz J., Hunt D.F. Peptide and Protein Sequence Analysis by Electron Transfer Dissociation Mass Spectrometry. Proc. Natl. Acad. Sci. U.S.A. 2004, 101:9528-9533.
4. Cooper H.J., Hakansson K., Marshall A.G. The Role of Electron Capture Dissociation in Biomolecular Analysis. Mass Spectrom. Rev. 2005, 24:201-222.
5. Zubarev R.A. Electron Capture Dissociation and Other Ion-Electron Fragmentation Reactions. Principles of Mass Spectrometry Applied to Biomolecules 2006, 475-517. John Wiley and Sons, New York. J. Laskin, C. Lifshitz (Eds.).
6. Breuker K. Protein Structure and Folding in the Gas Phase: Uniquitin and Cytochrome c. Principles of Mass Spectrometry Applied to Biomolecules 2006, 177-212. John Wiley and Sons., Inc, Hoboken, NJ. J. Laskin, C. Lifshitz (Eds.).
7. Hopkinson A.C., Siu K.W.M. Peptide Radical Cations. Principles of Mass Spectrometry Applied to Biomolecules 2006, 301-335. John Wiley and Sons., Inc, Hoboken, NJ. J. Laskin, C. Lifshitz (Eds.).
8. Gunawardena H.P., He M., Chrisman P.A., Pitteri S.J., Hogan J.M., Hodges B.D.M., McLuckey S.A. Electron Transfer Versus Proton Transfer in Gas-Phase Ion/Ion Reactions of Polyprotonated Peptides. J. Am. Chem. Soc. 2005, 127:12627-12639.
9. Turecek F., Chen X.H., Hao C.T. Where Does the Electron Go? Electron Distribution and Reactivity of Peptide Cation Radicals Formed by Electron Transfer in the Gas Phase. J. Am. Chem. Soc. 2008, 130:8818-8833.
10. Kjeldsen F., Silivra O.A., Ivonin I.A., Haselmann K.F., Gorshkov M., Zubarev R.A. C α-C Backbone Fragmentation Dominates in Electron Detachment Dissociation of Gas-Phase Polypeptide Polyanions. Chem. Eur. J. 2005, 11:1803-1812.
11. Antoine R., Joly L., Tabarin T., Broyer M., Dugourd P., Lemoine J. Photo-Induced Formation of Radical Anion Peptides. Electron Photodetachment Dissociation Experiments. Rapid Commun. Mass Spectrom. 2007, 21:265-268.
12. Pingitore F., Wesdemiotis C. Characterization of Dipeptide Isomers by Tandem Mass Spectrometry of Their Mono- Versus Dilithiated Complexes. Anal. Chem. 2005, 77:1796-1806.
13. Hu P.F., Loo J.A. Gas-Phase Coordination Properties of Zn2+, Cu2+, Ni2+, and Co2+ with Histidine-Containing Peptides. J. Am. Chem. Soc. 1995, 117:11314-11319.
14. Gatlin C.L., Rao R.D., Turecek F., Vaisar T. Carboxylate and Amine Terminus Directed Fragmentations in Gaseous Dipeptide Complexes with Copper(II) and Diimine Ligands Formed by Electrospray. Anal. Chem. 1996, 68:263-270.
15. Boutin M., Bich C., Afonso C., Fournier F., Tabet J.C. Negative-Charge Driven Fragmentations for Evidencing Zwitterionic Forms from Doubly Charged Coppered Peptides. J. Mass Spectrom. 2007, 42:25-35.
16. Turecek F. Copper-Biomolecule Complexes in the Gas Phase. The Ternary Way. Mass Spectrom. Rev. 2007, 26:563-582.
17. Chu I.K., Rodriquez C.F., Lau T.C., Hopkinson A.C., Siu K.W.M. Molecular Radical Cations of Oligopeptides. J. Phys. Chem. B 2000, 104:3393-3397.
18. Chu I.K., Rodriguez C.F., Rodriguez F., Hopkinson A.C., Siu K.W.M. Formation of Molecular Radical Cations of Enkephalin Derivatives Via Collision-Induced Dissociation of Electrospray-Generated Copper (II) Complex Ions of Amines and Peptides. J. Am. Soc. Mass Spectrom. 2001, 12:1114-1119.
19. Bagheri-Majdi E., Ke Y.Y., Orlova G., Chu I.K., Hopkinson A.C., Siu K.W.M. Copper-Mediated Peptide Radical Ions in the Gas Phase. J. Phys. Chem. B 2004, 108:11170-11181.
20. Chu I.K., Siu S.O., Lam C.N.W., Chan J.C.Y., Rodriquez C.F. Formation of Molecular Radical Cations of Aliphatic Tripeptides from Their Complexes with Cu-II(12-Crown-4). Rapid Commun. Mass Spectrom. 2004, 18:1798-1802.
21. Lam C.N.W., Ruan E.D.L., Ma C.Y., Chu I.K. Non-Zwitterionic Structures of Aliphatic-Only Peptides Mediated the Formation and Dissociation of Gas Phase Radical Cations. J. Mass Spectrom. 2006, 41:931-938.
22. Barlow C.K., Wee S., McFadyen W.D., O'Hair R.A.J. Designing Copper(II) Ternary Complexes to Generate Radical Cations of Peptides in the Gas Phase: Role of the Auxiliary Ligand. J. Chem. Soc. Dalton Trans. 2004, 20:3199-3204.
23. Barlow C.K., McFadyen W.D., O'Hair R.A.J. Formation of Cationic Peptide Radicals by Gas-Phase Redox Reactions with Trivalent Chromium, Manganese, Iron, and Cobalt Complexes. J. Am. Chem. Soc. 2005, 127:6109-6115.
24. Ke Y., Zhao J., Verkerk U.H., Hopkinson A.C., Siu K.W.M. Histidine, Lysine, and Arginine Radical Cations: Isomer Control Via the Choice of Auxiliary Ligand (L) in the Dissociation of [Cu-II(L)(Amino Acid)](·2+) Complexes. J. Phys. Chem. B 2007, 111:14318-14328.
25. Laskin J., Yang Z., Chu I.K. Energetics and Dynamics of Electron Transfer and Proton Transfer in Dissociation of MetalIII(Salen)-Peptide Complexes in the Gas Phase. J. Am. Chem. Soc. 2008, 130:3218-3230.
26. Masterson D.S., Yin H.Y., Chacon A., Hachey D.L., Norris J.L., Porter N.A. Lysine Peroxycarbamates: Free Radical-Promoted Peptide Cleavage. J. Am. Chem. Soc. 2004, 126:720-721.
27. Hodyss R., Cox H.A., Beauchamp J.L. Bioconjugates for Tunable Peptide Fragmentation: Free Radical Initiated Peptide Sequencing (FRIPS). J. Am. Chem. Soc. 2005, 127:12436-12437.
28. Hao G., Gross S.S. Electrospray Tandem Mass Spectrometry Analysis of S- and N-Nitrosopeptides: Facile Loss of NO and Radical-Induced Fragmentation. J. Am. Soc. Mass Spectrom. 2006, 17:1725-1730.
29. Wee S., Mortimer A., Moran D., Wright A., Barlow C.K., O'Hair R.A.J., Radom L., Easton C.J. Gas-Phase Regiocontrolled Generation of Charged Amino Acid and Peptide Radicals. Chem. Commun. 2006, 40:4233-4235.
30. Ly T., Julian R.R. Tracking Radical Migration in Large Hydrogen Deficient Peptides with Covalent Labels: Facile Movement Does Not Equal Indiscriminate Fragmentation. J. Am. Soc. Mass Spectrom. 2009, 20:1148-1158.
31. Ly T., Julian R.R. Residue-Specific Radical-Directed Dissociation of Whole Proteins in the Gas Phase. J. Am. Chem. Soc. 2008, 130:351-358.
32. Thompson M.S., Cui W.D., Reilly J.P. Fragmentation of Singly Charged Peptide ions by Photodissociation at λ = 157 nm. Angew. Chem. Int. Ed. 2004, 43:4791-4794.
33. Ly T., Julian R.R. Ultraviolet Photodissociation: Developments towards Applications for Mass-Spectrometry-Based Proteomics. Angew. Chem. Int. Ed. 2009, 48:7130-7137.
34. Hopkinson A.C. Radical Cations of Amino Acids and Peptides: Structures and Stabilities. Mass Spectrom. Rev. 2009, 28:655-671.
35. Wee S., O'Hair R.A.J., McFadyen W.D. Comparing the Gas-Phase Fragmentation Reactions of Protonated and Radical Cations of the Tripeptides GXR. Int. J. Mass Spectrom. 2004, 234:101-122.
36. Wee S., O'Hair R.A.J., McFadyen W.D. The Role of the Position of the Basic Residue in the Generation and Fragmentation of Peptide Radical Cations. Int. J. Mass Spectrom. 2006, 249:171-183.
37. Moran D., Jacob R., Wood G.P.F., Coote M.L., Davies M.J., O'Hair R.A.J., Easton C.J., Radom L. Rearrangements in Model Peptide-Type Radicals Via Intramolecular Hydrogen-Atom Transfer. Helv. Chim. Acta 2006, 89:2254-2272.
38. Leymarie N., Costello C.E., O'Connor P.B. Electron Capture Dissociation Initiates a Free Radical Reaction Cascade. J. Am. Chem. Soc. 2003, 125:8949-8958.
39. Pingitore F., Bleiholder C., Paizs B., Wesdemiotis C. Unimolecular Chemistry of Metal Ion-Coordinated α-Dipeptide Radicals. Int. J. Mass Spectrom. 2007, 265:251-260.
40. Chu I.K., Zhao J., Xu M., Siu S.O., Hopkinson A.C., Siu K.W.M. Are the Radical Centers in Peptide Radical Cations Mobile? The Generation, Tautomerism, and Dissociation of Isomeric α-Carbon-Centered Triglycine Radical Cations in the Gas Phase. J. Am. Chem. Soc. 2008, 130:7862-7872.
41. Sun Q., Nelson H., Ly T., Stoltz B.M., Julian R.R. Chain Chemistry Mediates Backbone Fragmentation in Hydrogen Deficient Peptide Radicals. J. Prot. Res. 2009, 8:958-966.
42. Zhang L., Reilly J.P. Radical-Driven Dissociation of Odd-Electron Peptide Radical Ions Produced in 157 nm Photodissociation. J. Am. Soc. Mass Spectrom. 2009, 20:1378-1390.
43. Laskin J., Futrell J.H., Chu I.K. Is Dissociation of Peptide Radical Cations an Ergodic Process?. J. Am. Chem. Soc. 2007, 129:9598-9599.
44. Laskin J. Energy and Entropy Effects in Gas-Phase Dissociation of Peptides and Proteins. Principles of Mass Spectrometry Applied to Biomolecules 2006, John Wiley and Sons., Inc, Hoboken, NJ. J. Laskin, C. Lifshitz (Eds.).
45. Laskin J., Yang Z.B., Lam C., Chu I.K. Charge-Remote Fragmentation of Odd-Electron Peptide Ions. Anal. Chem. 2007, 79:6607-6614.
46. Siu C.K., Ke Y., Orlova G., Hopkinson A.C., Siu K.W.M. Dissociation of the N-C-α Bond and Competitive Formation of the [z(n) - H](·+) and [c(n) + 2H](+) Product Ions in Radical Peptide Ions Containing Tyrosine and Tryptophan: The Influence of Proton Affinities on Product Formation. J. Am. Soc. Mass Spectrom. 2008, 19:1799-1807.
47. Varkey S.P., Ratnasamy C., Ratnasamy P. Zeolite-Encapsulated Manganese(III)Salen Complexes. J. Mol. Catal. A Chem. 1998, 135:295-306.
48. Wang P., Ohanessian G., Wesdemiotis C. Cu(II)-Catalyzed Reactions in Ternary [Cu(AA)(AA-H)](+) Complexes (AA = Gly, Ala, Val, Leu, Ile, t-Leu, Phe). Eur. J. Mass Spectrom. 2009, 15:325-335.
49. Yang Z.B., Lam C., Chu I.K., Laskin J. The Effect of the Secondary Structure on Dissociation of Peptide Radical Cations: Fragmentation of Angiotensin III and Its Analogues. J. Phys. Chem. B 2008, 112:12468-12478.
50. + ions of peptides. Side-Chain-Specific Sequence Ions. Int. J. Mass Spectrom. Ion Processes 1988, 86:137-154.
51. ·3+. J. Am. Soc. Mass Spectrom. 2005, 16:1795-1804.
52. · Ions Formed Via Gas-Phase Ion/Ion Electron-Transfer Dissociation. J. Proteome Res. 2007, 6:3062-3069.
53. Anusiewicz I., Jasionowski M., Skurski P., Simons J. Backbone and Side-Chain Cleavages in Electron Detachment Dissociation (EDD). J. Phys. Chem. A 2005, 109:11332-11337.
54. Huynh M.H.V., Meyer T.J. Proton-Coupled Electron Transfer. Chem. Rev. 2007, 107:5004-5064.
55. Laskin J., Bailey T.H., Futrell J.H. Fragmentation Energetics for Angiotensin II and Its Analogs from Time-and Energy-Resolved Surface-Induced Dissociation Studies. Int. J. Mass Spectrom. 2004, 234:89-99.
56. Hunt D.F., Yates J.R., Shabanowitz J., Winston S., Hauer C.R. Protein Sequencing by Tandem Mass Spectrometry. Proc. Natl. Acad. Sci. U.S.A. 1986, 83:6233-6237.
57. Schwartz B.L., Bursey M.M. Some Proline Substituent Effects in the Tandem Mass-Spectrum of Protonated Penta-Alanine. Biol. Mass Spectrom. 1992, 21:92-96.
58. Loo J.A., Edmonds C.G., Smith R.D. Tandem Mass Spectrometry of Very Large Molecules. 2. Dissociation of Multiply Charged Proline-Containing Proteins from Electrospray Ionization. Anal. Chem. 1993, 65:425-438.
59. Breci L.A., Tabb D.L., Yates J.R., Wysocki V.H. Cleavage N-Terminal to Proline: Analysis of a Database of Peptide Tandem Mass Spectra. Anal. Chem. 2003, 75:1963-1971.
60. Wood G.P.F., Moran D., Jacob R., Radom L. Bond Dissociation Energies and Radical Stabilization Energies Associated with Model Peptide-Backbone Radicals. J. Phys. Chem. A 2005, 109:6318-6325.