Fragmentation of protonated oligoalanines: Amide bond cleavage and beyond

Journal of the American Society for Mass Spectrometry

Volumn 15, Issue 12, 2004, Pages 1810-1819

  Harrison, Alex G ^a   Young, Alex B ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE BONDS; FRAGMENTATION REACTIONS; OLIGOALANINES;

CHEMICAL BONDS; DECOMPOSITION; MASS SPECTROMETRY; PROTONS;

REACTION KINETICS;

ALANINE DERIVATIVE; AMIDE; AMINO ACID; OXAZOLONE; PROTON;

ARTICLE; CARBOXY TERMINAL SEQUENCE; COLLISIONALLY ACTIVATED DISSOCIATION; DECOMPOSITION; FRAGMENTATION REACTION; MASS SPECTROMETRY; PROTON TRANSPORT;

ALANINE; AMIDES; OLIGOPEPTIDES; PROTONS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 10044229477     PISSN: 10440305     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jasms.2004.08.015     Document Type: Article

References (48)

1. C.M. Whitehouse, R.N. Dreyer, M. Yamashita, J.B. Fenn Electrospray Interface for Liquid Chromatographs and Mass Spectrometers Anal. Chem. 57 1985 675
2. R.B. Cole Electrospray Ionization Mass Spectrometry. Fundamentals, Instrumentation, and Applications 1997 Wiley New York
3. B.N. Pramanik A.K. Ganguly M.L. Gross Applied Electrospray Mass Spectrometry 2002 Marcel Dekker New York
4. M. Karas, F. Hillenkamp Laser Desorption Ionization of Proteins with Molecular Masses Exceeding 1000 Daltons Anal. Chem. 60 1988 2299
5. R.C. Beavis, B.T. Chait Matrix-Assisted Laser Desorption-Ionization Mass Spectrometry of Proteins Methods Enzymol. 270 1996 519
6. F.W. McLafferty Tandem Mass Spectrometry 1983 Wiley New York
7. K.L. Busch G.L. Glish S.A. McLuckey Mass Spectrometry/Mass Spectrometry Techniques and Applications of Tandem Mass Spectrometry 1988 VCH New York
8. P. Roepstorff, J. Fohlman Proposal for a Common Nomenclature for Sequence Ions in Mass Spectra of Peptides Biomed. Mass Spectrom. 11 1984 601
9. K. Biemann Contributions of Mass Spectrometry to Peptide and Protein Structure Biomed. Env. Mass Spectrom. 16 1988 99
10. K. Biemann Sequencing of Peptides by Tandem Mass Spectrometry and High-Energy Collision-Induced Dissociation Methods Enzymol. 193 1990 455
11. I.A. Papayannopoulos The Interpretation of Collision-Induced Dissociation Tandem Mass Spectra of Peptides Mass Spectrom. Rev. 14 1995 49
12. D.R. Mueller, M. Eckersley, W. Richter Hydrogen Transfer Reactions in the Formation of "Y + 2" Sequence Ions from Protonated Peptides Org. Mass Spectrom. 23 1988 217
13. M.M. Cordero, J.J. Houser, C. Wesdemiotis The Neutral Products Formed During Backbone Fragmentation of Protonated Peptides in Tandem Mass Spectrometry Anal. Chem. 65 1993 1594
14. T. Yalcin, C. Khouw, I.G. Csizmadia, M.R. Peterson, A.G. Harrison Why are B Ions Stable Species in Peptide Mass Spectra? J. Am. Soc. Mass Spectrom. 6 1995 1165
15. n (n < 3) Ions in Peptide Mass Spectra J. Am. Soc. Mass Spectrom. 7 1996 293
16. M.J. Nold, C. Wesdemiotis, T. Yalcin, A.G. Harrison Amide Bond Dissociation in Protonated Peptides. Structures of the N-Terminal Ionic and Neutral Fragments Int. J. Mass Spectrom. Ion Processes. 164 1997 137
17. + Ions from Protonated Peptides. An ab Initio Study Rapid Commun. Mass Spectrom. 13 1999 525
18. 2 Ions in Peptide Mass Spectra J. Am. Soc. Mass Spectrom. 11 2000 427
19. C.F. Rodriquez, T. Shoeib, I.K. Chu, K.W.M. Siu, A.C. Hopkinson Comparison Between Protonation, Lithiation, and Argentination of 5-Oxazolones. A Study of a Key Intermediate in Gas-Phase Peptide Sequencing J. Phys. Chem. A 104 2000 5355
20. J.M. Farrugia, T. Taverner, R.A.J. O'Hair Side-Chain Involvement in the Fragmentation Reactions of the Protonated Methyl Esters of Histidine and Its Peptides Int. J. Mass Spectrom. 209 2001 99
21. 2 Ions Have Oxazolone Structures? Mass Spectrometry and ab Initio Studies on Protonated N-Acyl Amino Acid Methyl Ester Model Systems Int. J. Mass Spectrom 210/211 2001 71
22. K. Ambihapathy, T. Yalcin, H.-W. Leung, A.G. Harrison Pathways to Immonium Ions in the Fragmentation of Protonated Peptides J. Mass Spectrom 32 1997 209
23. Aribi H. E.L., C.F. Rodriquez, D.R.P. Almeida, Y. Ling, W.W.-N. Mak, A.C. Hopkinson, K.W.M. Siu Elucidation of Fragmentation Mechanisms of Protonated Peptide Ions and Their Products A Case Study on Glycylglycylglycine Using Density Functional Theory and Threshold Collision-Induced Dissociation J. Am. Chem. Soc 125 2003 9229
24. R.W. Yeh, J.M. Grimsley, M.M. Bursey Collisionally Induced Fragmentation of Protonated Oligoalanines and Oligoglycines Biol. Mass Spectrom. 20 1991 443
25. B.L. Schwartz, M.M. Bursey Some Proline Substituent Effects in the Tandem Mass Spectrum of Protonated Pentaalanine Biol. Mass Spectrom. 21 1992 92
26. J. Laskin, E. Denisov, J. Futrell Comparative Study of Collision-induced and Surface-Induced Dissociation. 2. Fragmentation of Small Alanine-Containing Peptides in FT-ICR MS J. Phys. Chem. B 105 2001 1895
27. J. Laskin, E. Denisov, J. Futrell Fragmentation Energetics of Small Peptides from Multiple-Collision Activation and Surface-Induced Dissociation in FT-ICR MS Int. J. Mass Spectrom. 219 2002 189
28. J. Laskin, J. Futrell Surface-Induced Dissociation of Peptides Kinetics and Dynamics J. Am. Soc. Mass Spectrom. 14 2003 1340
29. B. Paizs, S. Suhai Towards Understanding the Tandem Mass Spectra of Protonated Oligopeptides 1 Mechanism of Amide Bond Cleavage J. Am. Soc. Mass Spectrom. 15 2004 103
30. A.G. Harrison Energy-Resolved Mass Spectrometry. A Comparison of Quadrupole Cell and Cone Voltage Collision-Induced Dissociation Rapid Commun. Mass Spectrom. 13 1999 1663
31. W.D. van Dongen, J.I.T. van Wijk, B.M. Green, W. Heerma, J. Haverkamp Comparison Between Collision Induced Dissociation of Electrosprayed Protonated Peptides in the Up-Front Region and in a Low-Energy Collision Cell Rapid Commun. Mass Spectrom 13 1999 1712
32. A.G. Harrison Fragmentation Reactions of Alkylphenyl Ammonium Ions J. Mass Spectrom. 34 1999 1253
33. J. Makowiecki, A. Tolonen, J. Uusitalo, J. Jalonen Cone Voltage and Collision Cell Collision-Induced Dissociation of Triphenylethylenes of Pharmaceutical Interest Rapid Commun. Mass Spectrom. 15 2001 1506
34. C. Buré, C. Lange Comparison of Dissociation of Ions in an Electrospray Source or a Collision Cell in Tandem Mass Spectrometry Curr. Org. Chem. 7 2003 1613
35. S.A. McLuckey, R.G. Cooks Angle- and Energy-Resolved Fragmentation from Tandem Mass Spectrometry F.W. McLafferty Tandem Mass Spectrometry 1983 Wiley New York 203
36. R.D. Smith, J.A. Loo, C.J. Barinaga, C.G. Edmonds, H.R. Udseth Collisional Activation and Collision-Activated Dissociation of Large Multiply Charged Polypeptides and Proteins Produced by Electrospray Ionization J. Am. Soc. Mass Spectrom. 1 1990 53
37. H. Chen, K. Tabei, M.M. Siegel Biopolymer Sequencing Using a Triple Quadrupole Mass Spectrometer in the ESI Nozzle-Skimmer/Precursor Ion MS/MS Mode J. Am. Soc. Mass Spectrom. 12 2001 846
38. 2 Ions Rapid Commun. Mass Spectrom. 16 2002 375
39. B. Paizs, S. Suhai Towards Understanding Some Ion Intensity Relationships for the Tandem Mass Spectra of Protonated Peptides Rapid Commun. Mass Spectrom. 16 2002 1699
40. B. Paizs, S. Suhai, A.G. Harrison Experimental and Theoretical Investigation of the Main Fragmentation Pathways of Protonated H-Gly-Gly-Sar-OH and H-Gly-Sar-Sar-OH J. Am. Soc. Mass Spectrom. 14 2003 1454
41. Paizs, B.; Suhai, S. Fragmentation Pathways of Protonated Peptides. Mass Spectrom. Rev., in press.
42. D.-C. Fang, T. Yalcin, T.-H. Tang, X.-Y. Fu, A.G. Harrison, I.G. Csizmadia Electron Distribution in Cationic Fragments Generated Mass Spectrometrically from Peptides J. Mol. Struct. (Theochem.) 468 1999 135
43. 3 Ions Derived from Protonated Peptides J. Mol. Struct. (Theochem.) 675 2004 79
44. P.G. Gassman, T.T. Tidwell Electron-Deficient Carbocations Acc. Chem. Res. 16 1983 279
45. H.-F. Grutzmacher, A.-M. Dommröse Kinetic Energy Release During CO Loss by Rearrangement of α-Benzoylcarbenium Ions Org. Mass Spectrom 18 1983 601
46. A.-M. Dommröse, H.-F. Grutzmacher Destabilized Carbenium Ions. Secondary and Tertiary α-Acetylbenzyl Cation and α-Benzoylbenzyl Cation Org. Mass Spectrom 22 1987 437
47. R. Wolf, H.-F. Grutzmacher Destabilized Carbenium Ions. α-Carbomethoxy-α,α-Dimethylmethyl Cation Org. Mass Spectrom. 24 1989 398
48. M. Tkaczyk, A.G. Harrison Formation of Destabilized Carbenium Ions by Charge Inversion of Negative Ions Int. J. Mass Spectrom. Ion Processes 109 1991 295