Cyclization Reaction of Peptide Fragment Ions during Multistage Collisionally Activated Decomposition: An Inducement to Lose Internal Amino-Acid Residues

Journal of the American Society for Mass Spectrometry

Volumn 18, Issue 4, 2007, Pages 663-678

  Jia, Chenxi ^a   Qi, Wei ^a   He, Zhimin ^a  

^a TIANJIN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLATION; CHEMICAL ACTIVATION; CHEMICAL MODIFICATION; CYCLIZATION; REACTION KINETICS;

COLLISIONALLY ACTIVATED DECOMPOSITION (CAD); FRAGMENTATION; PEPTIDE MODIFICATION; RING OPENING;

PEPTIDES;

AMIDE; AMINO ACID; ASPARAGINE; CYCLOPEPTIDE; GLUTAMINE; HELIUM; PEPTIDE FRAGMENT; PROLINE;

ACETYLATION; ARTICLE; COLLISIONALLY ACTIVATED DISSOCIATION; CYCLIZATION; FRAGMENTATION REACTION; PROTEIN MODIFICATION; PROTON TRANSPORT; RING OPENING;

AMINO ACID SEQUENCE; AMINO ACIDS; AMINOACYLATION; CYCLIZATION; MOLECULAR SEQUENCE DATA; PEPTIDE FRAGMENTS; PEPTIDES, CYCLIC; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 33947313512     PISSN: 10440305     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jasms.2006.12.002     Document Type: Article

References (48)

1. Domon B., and Aebersold R. Mass Spectrometry and Protein Analysis. Science 312 (2006) 212-217
2. Aebersold R., and Goodlett D.R. Mass Spectrometry in Proteomics. Chem. Rev 101 (2001) 269-295
3. Wysocki V.H., Resing K.A., Zhang Q.F., and Cheng G.L. Mass Spectrometry of Peptides and Proteins. Methods 35 (2005) 211-222
4. Forbes A.J., Patrie S.M., Taylor G.K., Kim Y.B., Jiang L.H., and Kelleher N.L. Targeted Analysis and Discovery of Posttranslational Modifications in Proteins from Methanogenic Archaea by Top-Down MS. Proc. Natl. Acad. Sci. U.S.A 101 (2004) 2678-2683
5. Zhong H.Y., Zhang Y., Wen Z.H., and Li L. Protein Sequencing by Mass Analysis of Polypeptide Ladders After Controlled Protein Hydrolysis. Nat. Biotechnol 22 (2004) 1291-1296
6. Dworzanski J.P., Snyder A.P., Chen R., Zhang H.Y., Wishart D., and Li L. Identification of Bacteria Using Tandem Mass Spectrometry Combined with a Proteome Database and Statistical Scoring. Anal. Chem 76 (2004) 2355-2366
7. Souza B.M., Marques M.R., Tomazela D.M., Eberlin M.N., Mendes M.A., and Palma M.S. Mass Spectrometric Characterization of Two Novel Inflammatory Peptides from the Venom of the Social Wasp. Polybia paulista. Rapid Commun. Mass Spectrom 18 (2004) 1095-1102
8. Brinkworth C.S., Bowie J.H., Bilusich D., and Tyler M.J. The rothein peptides from the skin secretion of Roth's tree frog Litoria rothii. Sequence determination using positive and negative ion electrospray mass spectrometry. Rapid Commun. Mass Spectrom 19 (2005) 2716-2724
9. n Characterization of Protonated Cyclic Peptides and Metal Complexes. J. Am. Soc. Mass Spectrom 15 (2004) 1039-1054
10. Ngoka L.C.M., and Gross M.L. Multistep Tandem Mass Spectrometry for Sequencing Cyclic Peptides in an Ion-Trap Mass Spectrometer. J. Am. Soc. Mass Spectrom 10 (1999) 732-746
11. Taylor S.W., Kassel D.B., Tincu J.A., and Craig A.G. Fragmentation of Tunichrome Sp-1 is Dominated by an Unusual Gas-Phase Intramolecular Rearrangement. J. Mass Spectrom 38 (2003) 1105-1109
12. O'Hair R.A.J. The Role of Nucleophile-Electrophile Interactions in the Unimolecular and Bimolecular Gas-Phase Ion Chemistry of Peptides and Related Systems. J. Mass Spectrom 35 (2000) 1377-1381
13. Polce M.J., Ren D., and Wesdemiotis C. Dissociation of the Peptide Bond in Protonated Peptides. J. Mass Spectrom 35 (2000) 1391-1398
14. Schlosser A., and Lehmann W.D. Five-Membered Ring Formation in Unimolecular Reactions of Peptides: A Key Structural Element Controlling Low-Energy Collision-Induced Dissociation of Peptides. J. Mass Spectrom 35 (2000) 1382-1390
15. 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
16. Paizs B., and Suhai S. Fragmentation Pathways of Protonated Peptides. Mass Spectrom. Rev 24 (2005) 508-548
17. Tang X.J., Thibault P., and Boyd R.K. 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
18. Tang X.J., and Boyd R.K. Rearrangements of Doubly Charged Acylium ions from Lysyl and Ornithyl Peptides. Rapid Commun. Mass Spectrom 8 (1994) 678-686
19. Vachet R.W., Bishop B.M., Erickson B.W., and Glish G.L. Novel Peptide Dissociation: Gas-Phase Intramolecular Rearrangement of Internal Amino Acid Residues. J. Am. Chem. Soc 119 (1997) 5481-5488
20. Craig A.G., and Taylor S.W. Fragmentation of a Novel Marine Peptide, Plicatamide, Involves an Unusual Gas-Phase Intramolecular Rearrangement. J. Am. Soc. Mass Spectrom 12 (2001) 470-474
21. Fuchs R., and Budzikiewicz H. Rearrangement Reactions in the Electrospray Ionization Mass Spectra of Pyoverdins. Int. J. Mass Spectrom 210 (2001) 603-612
22. Yague J., Paradela A., Ramos M., Ogueta S., Marina A., Barahona F., de Castro J.A.L., and Vazquez J. Peptide Rearrangement During Quadrupole Ion Trap Fragmentation: Added Complexity to MS/MS Spectra. Anal. Chem 75 (2003) 1524-1535
23. - parent anions of the antimicrobial peptide citropin 1.1 and Synthetically Modified Analogues Fragmentations which Require a Specific Conformation of the Decomposing Anion. Int. J. Mass Spectrom 236 (2004) 43-53
24. Harrison A.G., and Young A.B. Fragmentation of Protonated Oligoalanines: Amide Bond Cleavage and Beyond. J. Am. Soc. Mass Spectrom 15 (2004) 1810-1819
25. Harrison A.G., Young A.B., Bleiholder C., Suhai S., and Paizs B. Scrambling of Sequence Information in Collision-Induced Dissociation of Peptides. J. Am. Chem. Soc 128 (2006) 10364-10365
26. n-1 fragmentation pathways of protonated cyclic peptides. Eur. J. Mass Spectrom 12 (2006) 235-245
27. Stefanowicz P. Electrospray Mass Spectrometry and Tandem Mass Spectrometry of the Natural Mixture of Cyclic Peptides from Linseed. Eur. J. Mass Spectrom 10 (2004) 665-671
28. Grewal R.N., El Aribi H., Harrison A.G., Siu K.W.M., and Hopkinson A.C. Fragmentation of Protonated Tripeptides: The Proline Effect Revisited. J. Phys. Chem. B 108 (2004) 4899-4908
29. Jonsson A.P., Bergman T., Jornvall H., Griffiths W.J., Bratt P., and Stromberg N. Gln-Gly Cleavage: Correlation Between Collision-Induced Dissociation and Biological Degradation. J. Am. Soc. Mass Spectrom 12 (2001) 337-342
30. Harrison A.G. Fragmentation Reactions of Protonated Peptides Containing Glutamine or Glutamic Acid. J. Mass Spectrom 38 (2003) 174-187
31. Jia C.X., Qi W., He Z.M., Yang H.M., and Qiao B. Synthesis of Heptapeptides and Analysis of Sequence by Tandem Ion Trap Mass Spectrometry. Cent. Eur. J. Chem 4 (2006) 285-298
32. Roepstorff P., and Fohlman J. Proposal for a Common Nomenclature for Sequence Ions in Mass Spectra of Peptides. Biomed. Mass Spectrom 11 (1984) 601
33. Biemann K. Contributions of Mass Spectrometry to Peptide and Protein Structure. Biomed. Environ. Mass Spectrom 16 (1988) 99-111
34. Pettit G.R., Lippert J.W., Taylor S.R., Tan R., and Williams M.D. Synthesis of Phakellistatin 11: A Micronesia (Chuuk) Marine Sponge Cyclooctapeptide. J. Nat. Prod 64 (2001) 883-891
35. Forns P., Piro J., Cuevas C., Garcia M., Rubiralta M., Giralt E., and Diez A. Constrained Derivatives of Stylostatin 1. 1. Synthesis and Biological Evaluation as Potential Anticancer Agents. J. Med. Chem 46 (2003) 5825-5833
36. Vachet R.W., Ray K.L., and 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 (1998) 341-344
37. + ions of protonated peptides. An ab Initio Study. Rapid Commun. Mass Spectrom 14 (2000) 746-755
38. Chen X.H., and Turecek F. Simple b-Ions Have Cyclic Oxazolone Structures. A Neutralization-Reionization Mass Spectrometric and Computational Study of Oxazolone Radicals. J. Am. Soc. Mass Spectrom 16 (2005) 1941-1956
39. Jegorov A., Paizs B., Kuzma M., Zabka M., Landa Z., Sulc M., Barrow M.P., and Havlicek V. Extraribosomal Cyclic Tetradepsipeptides Beauverolides: Profiling and Modeling the Fragmentation Pathways. J. Mass Spectrom 39 (2004) 949-960
40. Paizs B., and Suhai S. Towards Understanding the Tandem Mass Spectra of Protonated Oligopeptides. 1: Mechanism of Amide Bond Cleavage. J. Am. Soc. Mass Spectrom 15 (2004) 103-113
41. 2 Ion. J. Am. Soc. Mass Spectrom 17 (2006) 20-28
42. Davies J.S. The Cyclization of Peptides and Depsipeptides. J. Pept. Sci 9 (2003) 471-501
43. Pettit G.R., Gao F., Cerny R.L., Doubek D.L., Tackett L.P., Schmidt J.M., and Chapuis J.C. Antineoplastic Agents. 278. Isolation and Structure of Axinastatins 2 and 3 from a Western Caroline Island Marine Sponge. J. Med. Chem 37 (1994) 1165-1168
44. Eckart K. Mass Spectrometry of Cyclic Peptides. Mass Spectrom. Rev 13 (1994) 23-55
45. Schilling B., Wang W., McMurray J.S., and Medzihradszky K.F. Fragmentation and Sequencing of Cyclic Peptides by Matrix-Assisted Laser Desorption/Ionization Post-Source Decay Mass Spectrometry. Rapid Commun. Mass Spectrom 13 (1999) 2174-2179
46. Vachet R.W., Asam M.R., and Glish G.L. Secondary Interactions Affecting the Dissociation Patterns of Arginine-Containing Peptide Ions. J. Am. Chem. Soc 118 (1996) 6252-6256
47. Fang S.P., Takao T., Satomi Y., Mo W.J., and Shimonishi Y. Novel Rearranged Ions Observed for Protonated Peptides via Metastable Decomposition in Matrix-Assisted Laser Desorption/Ionization Time-of-Flight Mass Spectrometry. J. Am. Soc. Mass Spectrom 11 (2000) 345-351
48. + Ion Structural Analogs by Solution-Phase Chemistry. J. Am. Soc. Mass Spectrom 16 (2005) 607-621