Derivatisation of arginine residues with malondialdehyde for the analysis of peptides and protein digests by LC-ESI-MS/MS

Journal of Mass Spectrometry

Volumn 41, Issue 5, 2006, Pages 623-632

  Foettinger, Alexandra ^a   Leitner, Alexander ^a   Lindner, Wolfgang ^a  

^a UNIVERSITY OF VIENNA   (Austria)

Author keywords

Arginine; Derivatisation; Malondialdehyde; Mass spectrometry; Peptides

Indexed keywords

CHEMICAL ANALYSIS; IONS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETERS; OPTIMIZATION; PROTEINS;

ACIDIC CONDITIONS; DERIVATISATION; PROTEIN IDENTIFICATION; PYRIMIDINE;

AMINES;

2 PYRIMIDINYLARGININE; ARGININE; GUANACLINE; MALONALDEHYDE; PEPTIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DERIVATIZATION; ELECTROSPRAY MASS SPECTROMETRY; ESTERIFICATION; FRAGMENTATION REACTION; LIQUID CHROMATOGRAPHY; PEPTIDE ANALYSIS; PRIORITY JOURNAL; PROTEIN MODIFICATION; QUANTITATIVE ANALYSIS; SENSITIVITY ANALYSIS;

ACIDS; ARGININE; CHROMATOGRAPHY, LIQUID; MALONDIALDEHYDE; PEPTIDES; PROTEOMICS; SENSITIVITY AND SPECIFICITY; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 33745786994     PISSN: 10765174     EISSN: 10969888     Source Type: Journal    
DOI: 10.1002/jms.1020     Document Type: Article

References (31)

1. Wysocki VH, Resing KA, Zhang Q, Cheng G. Mass spectrometry of peptides and proteins. Methods 2005; 35: 211.
2. Leitner A, Lindner W. Current chemical tagging strategies for proteome analysis by mass spectrometry. J. Chromatogr. B 2004; 813: 1.
3. Pütz S, Reinders J, Reinders Y, Sickmann A. Mass spectrometry-based peptide quantification: applications and limitations. Expert Rev. Proteomics 2005; 2: 381.
4. Heck AJR, Krijgsveld J. Mass spectrometry-based quantitative proteomics. Expert Rev. Proteomics 2004; 1: 317.
5. Garcia BA, Shabanowitz J, Hunt DF. Analysis of protein phosphorylation by mass spectrometry. Methods 2005; 35: 256.
6. Mukherji M. Phosphoproteomics in analyzing signaling pathways. Expert Rev. Proteomics 2005; 2: 117.
7. Aggarwal K, Choe LH, Lee KH. Quantitative analysis of protein expression using amine-specific isobaric tags in Escherichia coli cells expressing rhsA elements. Proteomics 2005; 5: 2297.
8. Chalkley RJ, Baker PR, Hansen KC, Medzihradszky KF, Allen NP, Rexach M, Burlingame AL. Comprehensive analysis of a multidimensional liquid chromatography mass spectrometry dataset acquired on a quadrupole selecting, quadrupole collision cell, time-of-flight mass spectrometer. I. How much of the data is theoretically interpretable by search engines? Mol. Cell. Proteomics 2005; 4: 1189.
9. Elias JE, Haas W, Faherty BK, Gygi SP. Comparative evaluation of mass spectrometry platforms used in large-scale proteomics investigations. Nat. Methods 2005; 2: 667.
10. Johnson RS, Davis MT, Taylor JA, Patterson SD. Informatics for protein identification by mass spectrometry. Methods 2005; 35: 223.
11. DeGnore JP, Qin J. Fragmentation of phosphopeptides in an ion trap mass spectrometer. J. Am. Soc. Mass Spectrom. 1998; 9: 1175.
12. Huang Y, Triscari JM, Tseng GC, Pasa-Tolic L, Lipton MS, Smith RD, Wysocki VH. Statistical characterization of the charge state and residue dependence of low-energy CID peptide dissociation patterns. Anal. Chem. 2005; 77: 5800.
13. Paizs B, Suhai S. Fragmentation pathways of protonated peptides. Mass Spectrom. Rev. 2005; 24: 508.
14. Leitner A, Lindner W. Probing of arginine residues in peptides and proteins using selective tagging and electrospray ionisation mass spectrometry. J. Mass Spectrom. 2003; 38: 891.
15. Leitner A, Lindner W. Effects of an arginine-selective tagging procedure on the fragmentation behavior of peptides studied by electrospray ionization tandem mass spectrometry (ESI-MS/MS). Anal. Chim. Acta 2005; 528: 165.
16. Leitner A, Lindner W. Functional probing of arginine residues in proteins using mass spectrometry and an arginine-specific covalent tagging concept. Anal. Chem. 2005; 77: 4481.
17. Foettinger A, Leitner A, Lindner W. Solid-phase capture and release of arginine peptides by selective tagging and boronate affinity chromatography. J. Chramatogr. A 2005; 1079: 187.
18. Dikler S, Kelly JW, Russell DH. Improving mass spectrometric sequencing of arginine-containing peptides by derivatization with acetylacetone. J. Mass Spectrom. 1997; 32: 1337.
19. Sullivan AG, Brancia FL, Tyldesley R, Bateman R, Khushwant S, Hubbard SJ, Oliver SG, Gaskell SJ. The exploitation of selective cleavage of singly protonated peptide ions adjacent to aspartic acid residues using a quadrupole orthogonal time-of-flight mass spectrometer equipped with a matrix-assisted laser desorption/ionization source. Int. J. Mass Spectrom. 2001; 210/211: 665.
20. Summerfield SG, Gaskell SJ. Fragmentation efficiencies of peptide ions following low energy collisional activation. Int. J. Mass Spectrom. Ion Process. 1997; 165: 509.
21. King TP. Selective chemical modification of arginyl residues. Biochemistry 1966; 5: 3454.
22. Perkins DN, Pappin DJ, Creasy DM, Cottrell JS. Probability-based protein identification by searching sequence databases using mass spectrometry data. Electrophoresis 1999; 20: 3551.
23. Hamberg M, Niehaus WG Jr, Samuelsson B. Preparation, isolation, and characterization of a derivative of malonaldehyde. Anal. Biochem. 1968; 22: 145.
24. Poon HF, Calabrese V, Scapagnini G, Butterfield DA. Free radicals: key to brain aging and heme oxygenase as a cellular response to oxidative stress. J. Gerontol. A Biol. Sci. Med. Sci. 2004; 59: 478.
25. Slatter DA, Murray M, Bailey AJ. Formation of a dihydropyridine derivative as a potential cross-link derived from malondialdehyde in physiological systems. FEBS Lett. 1998; 421: 180.
26. Slatter DA, Avery NC, Bailey AJ. Identification of a new cross-link and unique histidine adduct from bovine serum albumin incubated with malondialdehyde. J. Biol. Chem. 2004; 279: 61.
27. Slatter DA, Paul RG, Murray M, Bailey AJ. Reactions of lipid-derived malondialdehyde with collagen. J. Biol. Chem. 1999; 274: 19661.
28. Smolka MB, Albuquerque CPD, Chen S-h, Schmidt CH, Wei XX, Kolodner RD, Zhou H. Dynamic changes in protein-protein interaction and protein phosphorylation probed with amine reactive isotope tag. Mol. Cell. Proteomics 2005; 4: 1358.
29. Burlet O, Gaskell SJ. Decompositions of cationized heterodimers of amino acids in relation to charge location in peptide ions. J. Am. Soc. Mass Spectrom. 1993; 4: 461.
30. Nesvizhskii AI, Aebersold R. Interpretation of shotgun proteomics data: the protein inference problem. Mol. Cell. Proteomics 2005; 4: 1419.
31. Wu S-L, Kim J, Hancock WS, Karger B. Extended range proteomic analysis (ERPA): a new and sensitive LC-MS platform for high sequence coverage of complex proteins with extensive post-translational modifications-comprehensive analysis of beta-casein and epidermal growth factor receptor (EGFR). J. Proteome Res. 2005; 4: 1155.