Fragmentation reactions of methionine-containing protonated octapeptides and fragment ions therefrom: An energy-resolved study

Journal of the American Society for Mass Spectrometry

Volumn 24, Issue 10, 2013, Pages 1555-1564

  Harrison, Alex G ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

Cyclization reactions; N terminal fragment ions; Non direct sequence ions; Tandem mass spectrometry

Indexed keywords

CYCLIZATION REACTIONS; FRAGMENT IONS; FRAGMENTATION CHANNELS; FRAGMENTATION REACTIONS; LOW COLLISION ENERGY; REARRANGEMENT REACTIONS; SEQUENCE IONS; TANDEM MASS SPECTROMETRY;

AMINO ACIDS; CYCLIZATION; ELECTROSPRAY IONIZATION; MASS SPECTROMETERS; MASS SPECTROMETRY; PEPTIDES; PROTONATION;

IONS;

ALANINE; METHIONINE; OCTAPEPTIDE; OXAZOLONE;

AMINO ACID SEQUENCE; AMINO TERMINAL SEQUENCE; ARTICLE; CARBOXY TERMINAL SEQUENCE; CYCLIZATION; FRAGMENTATION REACTION; MACROCYCLIZATION; MASS SPECTROMETER; PROTEIN STRUCTURE; PROTON TRANSPORT; QUADRUPOLE MASS SPECTROMETRY; STRUCTURAL HOMOLOGY; TANDEM MASS SPECTROMETRY; TIME OF FLIGHT MASS SPECTROMETRY;

IONS; METHIONINE; OLIGOPEPTIDES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TANDEM MASS SPECTROMETRY;

EID: 84884542953     PISSN: 10440305     EISSN: 18791123     Source Type: Journal    
DOI: 10.1007/s13361-013-0706-x     Document Type: Article

References (50)

1. Larsen, M.R.; Roepstorff, P.: Mass spectrometric identification of proteins and characterization of their post-translational modifications in proteome analysis. Fresenius J. Anal. Chem. 366, 677-690 (2000)
2. Aebersold, R.; Goodlett, D.R.: Mass spectrometry in proteomics. Chem. Rev. 101, 269-295 (2001) (Pubitemid 32325797)
3. Medzihradszky, K.F.: Peptide sequence analysis. Methods Enzymol. 402, 209-244 (2005) (Pubitemid 43053129)
4. Paizs, B.; Suhai, S.: Fragmentation pathways of protonated peptides. Mass Spectrom. Rev. 24, 508-548 (2005) (Pubitemid 41083800)
5. Roepstorff, P.; Fohlman, J.: Proposals for a common nomenclature for sequence ions in mass spectra of peptides. Biomed. Mass Spectrom. 11, 601 (1984)
6. Biemann, K.: Contributions of mass spectrometry to peptide and protein structure. Biomed. Environ. Mass Spectrom. 16, 99-111 (1988) (Pubitemid 18265782)
7. Mueller, D.R.; Eckersley, M.; Richter, W.: Hydrogen transfer reactions in the formation of "Y+2" sequence ions from protonated peptides. Org. Mass Spectrom. 23, 217-222 (1988)
8. Cordero, M.M.; Houser, J.J.; Wesdemiotis, C.: The neutral products formed during backbone cleavage of protonated peptides in tandem mass spectrometry. Anal. Chem. 65, 1594-1601 (1993)
9. Harrison, A.G.: To b or not to b. The ongoing saga of peptide b ions. Mass Spectrom. Rev. 28, 640-654 (2009)
10. Farrugia, J.M.; Taverner, T.; 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, 99-112 (2001) (Pubitemid 32900646)
11. + ion. J. Am. Chem. Soc. 131, 17528-17529 (2009)
12. Zou, S.; Oomens, J.; Polfer, N.C.: Competition between diketopiperazine and oxazolone formation in water loss products from protonated ArgGly and GlyArg. Int. J. Mass Spectrom. 316/318, 12-17 (2012)
13. Yague, J.; Paradela, A.; Ramos, M.; Ogueta, S.; Marina, A.; Barabona, F.; Lopez de Castro, J.A.; Vazquez, J.: Peptide rearrangement during ion trap fragmentation. Added complexity to MS/MS spectra. Anal. Chem. 75, 1524-1535 (2003) (Pubitemid 36397187)
14. Harrison, A.G.; Young, A.B.; Bleiholder, C.; Suhai, S.; Paizs, B.: Scrambling of sequence information in collision-induced dissociation of peptides. J. Am. Chem. Soc. 128, 10364-10365 (2006) (Pubitemid 44265068)
15. Jia, C.; Qi, W.; He, Z.: Cyclization reactions of peptide fragment ions during multistage collisionally activated decomposition. An inducement to lose internal amino acid residues. J. Am. Soc. Mass Spectrom. 18, 663-678 (2007) (Pubitemid 46441875)
16. Mouls, L.; Aubagnac, J.L.; Martinez, J.; Enjalbal, C.: Low energy peptide fragmentation in an ESI-Q-TOF type mass spectrometer. J. Proteome Res. 6, 1378-1391 (2007) (Pubitemid 46724035)
17. Bleiholder, C.; Osburn, S.; Williams, T.D.; Suhai, S.; Van Stipdonk, M.; Harrison, A.G.; Paizs, B.: Sequence scrambling pathways of protonated peptides. J. Am. Chem. Soc. 130, 17774-17789 (2008)
18. 5 ions. J. Am. Soc. Mass Spectrom. 19, 1776-1780 (2008)
19. 9 ions. J. Am. Soc. Mass Spectrom. 20, 2248-2253 (2009)
20. 5 ions. J. Am. Chem. Soc. 131, 11503-11508 (2009)
21. Molesworth, S.; Osburn, S.; Van Stipdonk, M.: Influence of size on apparent scrambling of sequence during CID of b-type ions. J. Am. Soc. Mass Spectrom. 20, 2174-2181 (2009)
22. Fattahi, A.; Zekavat, B.; Solouki, T.: H/D exchange kinetics: evidence for formation of different b fragment conformers/isomers during gas-phase peptide sequencing. J. Am. Soc. Mass Spectrom. 21, 358-369 (2010)
23. 5 ions. J. Am. Soc. Mass Spectrom. 21, 1028-1036 (2010)
24. Bythell, B.J.; Knapp-Mohammady, M.; Paizs, B.; Harrison, A.G.: Effect of the His residue on the cyclization of b ions. J. Am. Soc. Mass Spectrom. 21, 1352-1363 (2010)
25. Atik, A.E.; Yalcin, T.: A systematic study of acidic peptides for b-type sequence scrambling. J. Am. Soc. Mass Spectrom. 22, 38-48 (2011)
26. 5 ions. J. Am. Soc. Mass Spectrom. 23, 594-601 (2012)
27. n (n = 5-7) ions. Int. J. Mass Spectrom. 316/318, 108-116 (2012)
28. Saminathan, I.S.; Wang, X.S.; Guo, Y.; Krakovska, O.; Voison, S.; Hopkinson, A.C.; Siu, K.W.M.: The extent and effects of peptide sequence scrambling via formation of macrocycylic b ions in model peptides. J. Am. Soc. Mass Spectrom. 21, 2085-2094 (2010)
29. Perkins, D.S.; Pappin, D.J.; Creasy, D.M.; Cottrell, J.S.: Probability-based protein identification by searching sequence databases using mass spectrometry data. Electrophoresis 20, 3551-3567 (1999) (Pubitemid 30007252)
30. Goloboroko, A.A.; Gorshkov, M.V.; Good, D.M.; Zubarev, R.A.: Sequence scrambling in shotgun proteomics is negligible. J. Am. Soc. Mass Spectrom. 22, 1121-1124 (2011)
31. Yu, L.; Tan, Y.; Tsai, Y.; Goodlett, D.R.; Polfer, N.C.: On the relevance of peptide sequence permutations in shotgun proteomics. J. Proteome Res. 10, 2409-2416 (2011)
32. Scherl, A.; Shaffer, S.A.; Taylor, G.K.; Hernandez, P.; Appel, R.D.; Binz, P.-A.; Goodlett, D.R.: On the benefits of acquiring peptide fragment ions at high measured mass accuracy. J. Am. Soc. Mass Spectrom. 19, 891-901 (2008)
33. Michalski, A.; Neuhauser, N.; Cox, J.; Mann, M.: A systematic investigation into the nature of tryptic HCD spectra. J. Prot. Res. 11, 5478-5491 (2012)
34. Wabnitz, P.A.; Bowie, J.H.; Wallace, J.C.; Tyler, M.J.: Peptides from the skin glands of the Australian buzzing tree frog Littoria electra. Comparison with the skin peptides of the red tree frog Littoria rubella. Aust. J. Chem. 52, 639-645 (1999)
35. Mouls, L.; Subra, G.; Aubagnac, J.-L.; Martinez, J.; Enjalbal, C.: Tandem mass spectrometry of amidated peptides. J. Mass Spectrom. 41, 1470-1483 (2006) (Pubitemid 44875657)
36. Langsdorf, M.; Ghassenpour, A.; Römpp, A.; Spengler, B.: Characterization of a peptide family from the skin secretions of the middle east tree frog Hyla savignyi by composition-based de novo sequencing. Rapid Commun. Mass Spectrom. 24, 2885-2899 (2010)
37. Samigna, T.Y.; Gorshkov, V.V.; Artemenko, K.A.; Kovalev, S.V.; Ogourtsov, S.V.; Zubarev, R.A.; Lebedev, A.T.: Novel natural peptides from Hydra arborea schelkownikowi skin secretion. Rapid Commun. Mass Spectrom. 24, 1749-1754 (2010)
38. Yalcin, T.; Khouw, C.; Csizmadia, I.G.; Peterson, M.R.; Harrison, A.G.: Why are b ions stable species in peptide mass spectra. J. Am. Soc. Mass Spectrom. 6, 1165-1174 (1995)
39. n (n ≥ 3) ions in peptide mass spectra. J. Am. Soc. Mass Spectrom. 7, 233-242 (1996)
40. Ambihapathy, K.; Yalcin, T.; Leung, H.-W.; Harrison, A.G.: Pathways to immonium ions in the fragmentation of protonated peptides. J. Mass Spectrom. 32, 209-215 (1997) (Pubitemid 27087387)
41. Vachet, R.W.; Kay, K.L.; Glish, G.L.: Origin of product ions in the MS/MS spectra of peptides in a quadrupole ion trap. J. Am. Soc. Mass Spectrom. 9, 341-344 (1998) (Pubitemid 34436860)
42. El Aribi, H.; Rodriquez, C.F.; Almeida, D.R.P.; Ling, Y.; Mak, W.W.-N.; Hopkinson, A.C.; Siu, K.W.M.: Elucidation of fragmentation mechanisms of protonated peptides and their products: a case study on glycylglycylglycine using density functional theory and threshold collision-induced dissociation. J. Am. Chem. Soc. 125, 9229-9236 (2003) (Pubitemid 36903837)
43. 1-protonated 4-imidazolidinone. J. Phys. Chem. Lett. 1, 868-872 (2010)
44. n fragment ions of protonated peptides. J. Am. Chem. Soc. 132, 14766-14779 (2010)
45. Savitski, M.M.; Fälth, M.; Fung, Y.M.E.; Adams, C.M.; Zubarev, R.A.: Bifurcating fragmentation behavior of gas-phase tryptic peptide dications in collisional activation. J. Am. Soc. Mass Spectrom. 19, 1755-1763 (2008)
46. 3 ions rarely observed? J. Am. Soc. Mass Spectrom. 19, 1764-1770 (2008)
47. 4 ion of protonated YGGFL characterized by IR spectroscopy and modeling. J. Am. Soc. Mass Spectrom. 23, 664-675 (2012)
48. Wassermann, T.N.; Boyarkin, O.V.; Paizs, B.; Rizzo, T.R.: Conformation-specific spectroscopy of peptide fragment ions in a low-temperature ion trap. J. Am. Soc. Mass Spectrom. 23, 1029-1045 (2012)
49. Vachet, R.W.; Bishop, B.M.; Erickson, B.W.; Glish, G.L.: Novel peptide dissociation: gas-phase intramolecular rearrangement of internal amino acid residues. J. Am. Chem. Soc. 119, 5481-5488 (1997) (Pubitemid 27321407)
50. Harrison, A.G.; Young, A.B.: Fragmentation of protonated oligoalanines. Amide bond cleavage and beyond. J. Am. Soc. Mass Spectrom. 15, 1810-1819 (2004) (Pubitemid 39602731)