Apparent inhibition by arginine of macrocyclic b ion formation from singly charged protonated peptides

Journal of the American Society for Mass Spectrometry

Volumn 21, Issue 8, 2010, Pages 1322-1328

  Molesworth, Samuel P ^a   Van Stipdonk, Michael J ^a  

^a WICHITA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; ARGININE; DRUG PRODUCTS; ISOMERS; MASS SPECTROMETRY; PEPTIDES; PLANTS (BOTANY); PROTONATION;

ARGININE RESIDUE; COLLISION INDUCED DISSOCIATION; DIRECT SEQUENCE; FRAGMENTATION PATTERNS; PEPTIDE SEQUENCES; PROTONATED PEPTIDES; SEQUENCE INFORMATIONS; TANDEM MASS SPECTROMETRY;

IONS;

ARGININE; MACROCYCLIC COMPOUND; PEPTIDE; PROTON;

AMINO ACID SEQUENCE; AMINO TERMINAL SEQUENCE; ARTICLE; CARBOXY TERMINAL SEQUENCE; COLLISIONALLY ACTIVATED DISSOCIATION; ELECTROSPRAY MASS SPECTROMETRY; FRAGMENTATION REACTION; INHIBITION KINETICS; PEPTIDE ANALYSIS; PROTEIN DEGRADATION; PROTEIN MODIFICATION; PROTON TRANSPORT; SURFACE CHARGE; CHEMICAL STRUCTURE; CHEMISTRY; METHODOLOGY; TANDEM MASS SPECTROMETRY;

ARGININE; MACROCYCLIC COMPOUNDS; MODELS, MOLECULAR; PEPTIDES; PROTONS; TANDEM MASS SPECTROMETRY;

EID: 79952503640     PISSN: 10440305     EISSN: 18791123     Source Type: Journal    
DOI: 10.1016/j.jasms.2010.02.010     Document Type: Article

References (42)

1. Roepstroff, P.; Fohlmann, J. Proposal for a Common Nomenclature for Sequence Ions in Mass Spectra of Peptides. J. Biomed. Mass Spectrom. 1984, 11, 601.
2. Papayannopoulos, I. A. The Interpretation of Collision-Induced Dissociation Tandem Mass Spectra of Peptides. 1995, 14, 49-73.
3. (a) Dongre, A. R.; Jones, J. L.; Somogyi, A.; Wysocki, V. H. Influence of Peptide Composition, Gas-Phase Basicity, and Chemical Modification on Fragmentation Efficiency: Evidence for the Mobile Proton Model. J. Am. Chem. Soc. 1996, 118, 8365-8374.
4. (b) Wysocki, V. H.; Tsaprailis, G.; Smith, L. L.; Breci, L. A. Mobile and Localized Protons: A Framework for Understanding Peptide Dissociation. J. Mass Spectrom. 2000, 35, 1399-1406.
5. (c) Jones, J. L.; Dongre, A. R.; Somogyi, A.; Wysocki, V. H. Sequence Dependence of Peptide Fragmentation Efficiency Curves Determined by Electrospray Ionization/Surface-Induced Dissociation Mass Spectrometry. J. Am. Chem. Soc. 1994, 116, 8368-8369.
6. (a) Burlet, O.; Yang, C. Y.; Gaskell, S. J. Influence of Cysteine to Cysteic Acid Oxidation on the Collision-Activated Decomposition of Protonated Peptides: Evidence for Intraionic Interactions. J. Am. Soc. Mass Spectrom. 1992, 3, 337-344.
7. (b) Cox, K. A.; Gaskell, S. J.; Morris, M. Whiting, A. Role of the Site of Protonation in the Low-Energy Decompositions of Gas-Phase Peptide Ions. J. Am. Soc. Mass Spectrom. 1996, 7, 522-531.
8. (c) Summerfield, S. G.; Whiting, A.; Gaskell, S. J. Intraionic Interactions in Electrosprayed Peptide Ions. Int. J. Mass Spectrom. Ion Processes 1997, 162, 149-161.
9. Yalcin, T.; Csizmadia, I. G.; Peterson, M. B.; Harrison, A. Why are b Ions Stable Species in Peptide Spectra? J. Am. Soc. Mass Spectrom. 1996, 7, 233-242.
10. + Ions from Protonated Peptides: An Ab Initio Study. Rapid Commun. Mass Spectrom. 1999, 13, 525-533.
11. Paizs, B.; Suhai, S. Towards Understanding the Tandem Mass Spectra of Protonated Oligopeptides. 1: Mechanism of Amide Bond Cleavage. J. Am. Soc. Mass Spectrom. 2004, 15, 103-113.
12. 2 ions. Rapid Commun. Mass Spectrom. 2002, 16, 375-389.
13. Polce, M. J.; Ren, D.; Wesdemiotis, C. Dissociation of the Peptide Bond in Protonated Peptides. J. Mass Spectrom. 2000, 35(12), 1391-1398.
14. Paizs, B.; Suhai, S. Fragmentation Pathways of Protonated Peptides. Mass Spectrom. Rev. 2004, 24, 508-548.
15. n (n ≥ 3) Ions in Peptide Spectra. J. Am. Soc. Mass Spectrom. 1995, 6, 1165-1174.
16. Oomens, J.; Young S.; Molesworth, S.; van Stipdonk, M. Spectroscopic Evidence for an Oxazolone Structure of the b2 Fragment Ion from Protonated Tri-Alanine. J. Am. Soc. Mass Spectrom. 2009, 20, 334-339.
17. + Ion. J. Am. Chem. Soc. 2008, 130, 17644-17645.
18. Bythell, B. J.; Erlekam, U.; Paizs, B.; Maitre, P. Infrared Spectroscopy of Fragments from Doubly Protonated Tryptic Peptides. Chem. Phys. Chem. 2009, 10, 883-885.
19. Chen, X.; Yu, L.; Steill, J. D.; Oomens, J.; Polfer, N. C. Effect of Peptide Fragment Size on the Propensity of Cyclization in Collision-Induced Dissociation: Oligoglycine b2-b8. J. Am. Chem. Soc. 2009, 131, 18272-18282.
20. Polfer, N. C.; Oomens, J.; Suhai, S.; Paizs, B. Spectroscopic and Theoretical Evidence for Oxazolone Ring Formation in Collision-Induced Dissociation of Peptides. J. Am. Chem. Soc. 2005, 127, 7154-17155.
21. Harrison, A. G.; Young, A. B.; Bleiholder, B.; Suhai, S.; Paizs, B. Scrambling of Sequence Information in Collision-Induced Dissociation of Peptides. J. Am. Chem. Soc. 2006, 128, 10364-10365.
22. Riba-Garcia, F.; Giles, K.; Bateman, R. H.; Gaskell, S. J. Evidence for Structural Variants of a- and b-Type Peptide Fragment Ions Using Combined Ion Mobility/Mass Spectrometry. J. Am. Soc. Mass Spectrom. 2008, 19, 609-613.
23. Bleiholder, C.; Osburn, S.; Williams, T. D.; Suhai, S.; Van Stipdonk, M.; Harrison, A. G.; Paizs, B. Sequence Scrambling Fragmentation Pathways of Protonated Peptides. J. Am. Chem. Soc. 2008, 130, 17774-17789.
24. Jia, C.; Qi, W.; He, Z. Cyclization Reaction of Peptide Fragment Ions during Multistage Collisionally Activated Decomposition: An Inducement to Lose Internal Amino-Acid Residues. J. Am. Soc. Mass Spectrom. 2007, 18, 663-667.
25. 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. 2009, 20, 2174-2181.
26. 9 Ions. J. Am. Soc. Mass Spectrom. 2009, 20, 2248-2253.
27. 5 Ions. J. Am. Chem. Soc. 2009, 131, 11503-11508.
28. Olsen, J. V.; Mann, M. Improved Peptide Identification in Proteomics by Two Consecutive Stages of Mass Spectrometric Fragmentation. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 13417-13422.
29. Farrugia, J. M.; O'Hair, R. A. J. Involvement of Salt Bridges in a Novel Gas Phase Rearrangement of Protonated Arginine-Containing Dipeptides, Which Precedes Fragmentation. Int. J. Mass Spectrom. 2003, 222, 229-242.
30. 2. Int. J. Mass Spectrom. 2002, 219, 203-232.
31. Farrugia, J. M.; O'Hair, R. A. J.; Reid, G. E. Do All b2 Ions Have Oxazolone Structures? Multistage Mass Spectrometry and Ab Initio Studies on Protonated N-Acyl Amino Acid Methylester Model Systems. Int. J. Mass Spectrom. 2001, 210/211, 71-87.
32. Yalcin, T.; Harrison, A. G. Ion Chemistry of Protonated Lysine Derivatives. J. Mass Spectrom. 1996, 31, 1237-1243.
33. Kish, M. M.; Wesdemiotis, C. Selective Cleavage at Internal Lysine Residues in Protonated vs. Metalated Peptides. Int. J. Mass Spectrom. 2003, 227, 191-203.
34. Molesworth, S.; Leavitt, C. M.; Groenewold, G. S.; Oomens, J.; Steill, J.; Van Stipdonk, M. Spectroscopic Evidence for Mobilization of Amide Position Protons During CID of Model Peptide Ions. J. Am. Soc. Mass Spectrom. 2009, 20, 1841-1845.
35. Bythell, B. J.; Suhai, S.; Somogyi, A.; Paizs, B. Proton-Driven Amide Bond-Cleavage Pathways of Gas-Phase Peptide Ions Lacking Mobile Protons. J. Am. Chem. Soc. 2009, 131, 14057-14065.
36. 5 Ions. J. Am. Soc. Mass Spectrom. 2009, unpublished, (submitted).
37. Dormady, S. J.; Lei, J.; Regnier, F. E. Eliminating Disulfide Exchange During Glutamyl Endopeptidase Digestion of Native Protein. J. Chromatogr. A 1999, 864, 237-245.
38. Milgotina, E. I.; Voyushina, T. L.; Chestukhina, G. G. Glutamyl Endopeptidases: Structure, Function, and Practical Application. Russ. J. Bioorgan. Chem. 2003, 29, 511-522.
39. Houmard, J.; Drapeau, G. R. Staphylococcal Protease: A Proteolytic Enzyme Specific for Glutamoyl Bonds. Proc. Nat. Acad. Sci. U.S.A. 1972, 69, 3506-3509.
40. Fernandez, J.; Mische, S. M. Enzymatic Digestion of Membrane-Bound Proteins for Peptide Mapping and Internal Sequence Analysis. In The Protein Protocols Handbook 2nd ed., Walker, J. M. Ed.; Humana Press: Totowa, NJ, p. 523-532.
41. Chan, W. C.; White, P. D. Fmoc Solid Phase Peptide Synthesis-A Practical Approach; Oxford University Press: New York, 2000.
42. Barr, J. M.; Van Stipdonk, M. J. Multi-Stage Tandem Mass Spectrometry of Metal Cationized Leucine Enkephalin and Leucine Enkephalin Amide. Rapid Commun. Mass Spectrom. 2002, 16, 566-578