The role of lysine ε-amine group on the macrocyclization of b ions

International Journal of Mass Spectrometry

Volumn 316-318, Issue , 2012, Pages 84-90

  Atik, A Emin ^a   Gorgulu, Guvenc ^a   Yalcin, Talat ^a  

^a IZMIR INSTITUTE OF TECHNOLOGY   (Turkey)

Author keywords

Asparagine; Glutamine; Lysine side chain amine group; Macrocyclization of b ions; N terminal acetylation

Indexed keywords

EID: 84860522272     PISSN: 13873806     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijms.2011.12.008     Document Type: Article

References (41)

1. D.F. Hunt, J.R. Yates III, J. Shabanonowitz, S. Winston, and C.R. Hauer Protein sequencing by tandem mass spectrometry Proc. Natl. Acad. Sci. U.S.A. 83 1986 6233 6237 (Pubitemid 17174712)
2. J.B. Fenn, M. Mann, C.K. Meng, S.F. Wong, and C.M. Whitehouse Electrospray ionization mass spectrometry of large molecules Science 246 1989 64 71 (Pubitemid 19252085)
3. M. Karas, and F. Hillenkamp Laser desorption ionization of proteins with molecular masses exceeding 10,000 Da Anal. Chem. 60 1988 2299 2301
4. K. Tanaka, H. Waki, Y. Ido, S. Akita, Y. Yoshida, T. Yoshida, and T. Matsuo Protein and polymer analyses up to m/z 100,000 by laser ionization time-of-flight mass spectrometry Rapid Commun. Mass Spectrom. 2 1988 151 153
5. P. Roepstorff, and J. Fohlmann Proposals for a common nomenclature for sequence ions in mass spectra of peptides Biomed. Mass Spectrom. 11 1984 601
6. K. Biemann Contributions of mass spectrometry to peptide and protein structure Biomed. Environ. Mass Spectrom. 16 1988 99 111 (Pubitemid 18265782)
7. D.R. Mueller, M. Eckersley, and W. Richter Hydrogen transfer reactions in the formation of "Y+2" sequence ions from protonated peptides Org. Mass Spectrom. 23 1988 217 222
8. M.M. Cordero, J.J. Houser, and C. Wesdemiotis The neutral products formed during backbone cleavage of protonated peptides in tandem mass spectrometry Anal. Chem. 65 1993 1594 1601
9. T. Yalcin, C. Khouw, I.G. Csizmadia, M.R. Peterson, and A.G. Harrison Why are b ions stable species in peptide spectra? J. Am. Soc. Mass Spectrom. 6 1995 1165 1174
10. n (n ≥ 3) ions in peptide mass spectra J. Am. Soc. Mass Spectrom. 7 1996 233 242
11. + ions from protonated peptides: an ab initio study Rapid Commun. Mass Spectrom. 13 1999 525 533 (Pubitemid 29139215)
12. M.J. Polce, D. Ren, and C. Wesdemiotis Dissociation of the peptide bond in protonated peptides J. Mass Spectrom. 35 12 2000 1391 1398 (Pubitemid 32063645)
13. B. Paizs, and S. Suhai Towards understanding the tandem mass spectra of protonated oligopeptides 1: mechanism of amide bond cleavage J. Am. Soc. Mass Spectrom. 15 2004 103 113 (Pubitemid 38091672)
14. N.C. Polfer, J. Oomens, S. Suhai, and B. Paizs Spectroscopic and theoretical evidence for oxazolone ring formation in collision-induced dissociation of peptides J. Am. Chem. Soc. 127 2005 17154 17155 (Pubitemid 41791013)
15. N.C. Polfer, J. Oomens, S. Suhai, and B. Paizs Infrared spectroscopy and theoretical studies on gas-phase protonated leu-enkephalin and its fragments: direct experimental evidence for the mobile proton J. Am. Chem. Soc. 129 2007 5887 5897 (Pubitemid 46748493)
16. B.J. Bythell, U. Erlekam, B. Paizs, and P. Maitre Infrared spectroscopy of fragments from doubly protonated tryptic peptides Chem. Phys. Chem. 10 2009 883 885
17. 2 ions generated from doubly protonated tryptic peptides? J. Am. Soc. Mass Spectrom. 20 2009 618 624
18. 2 ion J. Am. Soc. Mass Spectrom. 17 2006 20 28 (Pubitemid 43033279)
19. + ion J. Am. Chem. Soc. 131 2009 17528 17529
20. B. Paizs, and S. Suhai Fragmentation pathways of protonated peptides Mass Spectrom. Rev. 24 2005 508 548
21. R.W. Vachet, B.M. Bishop, B.W. Erickson, and G.L. Glish Novel peptide dissociation: gas-phase intermolecular rearrangement of internal amino acid residues J. Am. Chem. Soc. 119 24 1997 5481 5488 (Pubitemid 27321407)
22. J. Yagüe, A. Paradela, M. Ramos, S. Ogueta, A. Marina, F. Barabona, J.A. Lopez de Castro, and J. Vazquez Peptide rearrangement during ion trap fragmentation: added complexity to MS/MS spectra Anal. Chem. 75 2003 1524 1535 (Pubitemid 36397187)
23. A.G. Harrison, A.B. Young, C. Bleiholder, S. Suhai, and B. Paizs Scrambling of sequence information in collision-induced dissociation of peptides J. Am. Chem. Soc. 128 2006 10364 10365 (Pubitemid 44265068)
24. C. Jia, W. Qi, and Z. He 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 2007 663 678 (Pubitemid 46441875)
25. C. Bleiholder, S. Osburn, T.D. Williams, S. Suhai, M. Van Stipdonk, A.G. Harrison, and B. Paizs Sequence-scrambling pathways of protonated peptides J. Am. Chem. Soc. 130 2008 17774 17789
26. 5 ions J. Am. Soc. Mass Spectrom. 19 2008 1776 1780
27. 5 ions J. Am. Chem. Soc. 131 2009 11503 11508
28. N.C. Polfer, B.C. Bohrer, M.D. Plasencia, B. Paizs, and D.E. Clemmer On the dynamics of fragment isomerization in collision-induced dissociation of peptides J. Phys. Chem. A 112 2008 1286 1293 (Pubitemid 351316296)
29. I. Riba-Garcia, K. Giles, R.H. Bateman, and S.J. Gaskell Evidence for structural variants of a- and b-type peptide fragment ions using combined ion mobility/mass spectrometry J. Am. Soc. Mass Spectrom. 19 2008 609 613
30. B.J. Bythell, M. Knapp-Mohammady, B. Paizs, and A.G. Harrison Effect of the his residue on the cyclization of b ions J. Am. Soc. Mass Spectrom. 21 2010 1352 1363
31. S. Molesworth, and M. Van Stipdonk Apparent inhibition by arginine of macrocyclic b ion formation from singly charged protonated peptides J. Am. Soc. Mass Spectrom. 21 2010 1322 1328
32. A.E. Atik, and T. Yalcin A systematic study of acidic peptides for b-type sequence scrambling J. Am. Soc. Mass Spectrom. 22 2011 38 48
33. 5 ions J. Am. Soc. Mass Spectrom. 21 2010 1028 1036
34. S. Molesworth, S. Osburn, and M. Van Stipdonk Influence of size on apparent scrambling of sequence during CID of b-type ions J. Am. Soc. Mass Spectrom. 20 2009 2174 2181
35. 8 J. Am. Chem. Soc. 131 2009 18272 18282
36. 9 ions J. Am. Soc. Mass Spectrom. 20 2009 2248 2253
37. I.S. Saminathan, X.S. Wang, Y. Guo, O. Krakovska, S. Voisin, A.C. Hopkinson, and K.W. Siu The extent and effects of peptide sequence scrambling via formation of macrocyclic b ions in model proteins J. Am. Soc. Mass Spectrom. 21 2010 2085 2094
38. X.J. Tang, and R.K. Boyd Rearrangements of doubly-charged acylium ions from lysyl and ornithyl peptides Rapid Commun. Mass Spectrom. 8 1994 678 686 (Pubitemid 2139483)
39. X.J. Tang, P. Thibault, and R.K. Boyd Fragmentation reactions of multiply-protonated peptides and implications for sequencing by tandem mass-spectrometry with low-energy collision-induced dissociation Anal. Chem. 65 1993 2824 2834
40. T. Yalcin, and A.G. Harrison Ion chemistry of protonated lysine derivatives J. Mass Spectrom. 31 1996 1237 1243 (Pubitemid 26392418)
41. X. Li, Y. Huang, P.B. O'Connor, and C. Lin Structural heterogeneity of doubly-charged peptide b-ions J. Am. Soc. Mass Spectrom. 22 2011 245 254