Development of a novel imidazolium-based aromatic quaternary ammonium tag: Synthesis and application to the efficient analysis of cysteinyl-peptides by mass spectrometry

Rapid Communications in Mass Spectrometry

Volumn 28, Issue 3, 2014, Pages 256-264

  Qiao, Xiaoqiang ^a   Wang, Rui ^a,b   Yan, Hongyuan ^a   Wang, Tao ^a   Zhao, Qun ^b   Zhang, Lihua ^b   Zhang, Yukui ^b  

^a HEBEI UNIVERSITY   (China)

^b INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALINITY; AROMATIC COMPOUNDS; BODY FLUIDS; DESORPTION; EFFICIENCY; ELECTROSPRAY IONIZATION; IONIZATION OF GASES; MASS SPECTROMETRY;

CHARGE STATE; CHEMICAL DERIVATIZATION; DERIVATIZATIONS; EFFICIENT ANALYSIS; IMIDAZOLIUM-BASED; IONIZATION CHARGE; IONIZATION EFFICIENCY; MODEL PEPTIDES; PEPTIDE IDENTIFICATION; QUATERNARY AMMONIUM;

PEPTIDES;

CYSTEINE; IMIDAZOLE; IMIDAZOLE DERIVATIVE; PEPTIDE FRAGMENT; PROTEIN; QUATERNARY AMMONIUM DERIVATIVE;

ANIMAL; ARTICLE; CATTLE; CHEMISTRY; GENETIC PROCEDURES; METHODOLOGY; TANDEM MASS SPECTROMETRY;

ANIMALS; CATTLE; CYSTEINE; IMIDAZOLES; MOLECULAR PROBE TECHNIQUES; PEPTIDE FRAGMENTS; PROTEINS; QUATERNARY AMMONIUM COMPOUNDS; TANDEM MASS SPECTROMETRY;

EID: 84891274299     PISSN: 09514198     EISSN: 10970231     Source Type: Journal    
DOI: 10.1002/rcm.6785     Document Type: Article

References (37)

1. R. Aebersold, M. Mann,. Mass spectrometry-based proteomics. Nature 2003, 422, 198.
2. B. T. Chait,. Mass spectrometry: Bottom-up or top-down? Science 2006, 314, 65.
3. X. Qiao, D. Tao, Y. Qu, L. Sun, L. Gao, X. Zhang, Z. Liang, L. Zhang, Y. Zhang,. Large-scale N-glycoproteome map of rat brain tissue: simultaneous characterization of insoluble and soluble protein fractions. Proteomics 2011, 11, 4274.
4. A. A. Lobas, A. N. Verenchikov, A. A. Goloborodko, L. I. Levitsky, M. V. Gorshkov,. Combination of Edman degradation of peptides with liquid chromatography/mass spectrometry workflow for peptide identification in bottom-up proteomics. Rapid Commun. Mass Spectrom. 2013, 27, 391.
5. A. Pashkova, E. Moskovets, B. L. Karger,. Coumarin tags for improved analysis of peptides by MALDI-TOF MS and MS/MS. 1. Enhancement in MALDI MS signal intensities. Anal. Chem. 2004, 76, 4550.
6. G. Hart-Smith, M. J. Raftery,. Detection and characterization of low abundance glycopeptides via higher-energy C-trap dissociation and orbitrap mass analysis. J. Am. Soc. Mass Spectrom. 2012, 23, 124.
7. F. Xu, L. Zou, Y. Liu, Z. Zhang, C. N. Ong,. Enhancement of the capabilities of liquid chromatography-mass spectrometry with derivatization: general principles and applications. Mass Spectrom. Rev. 2011, 30, 1143.
8. J. Zhang, R. Al-Eryani, H. L. Ball,. Mass spectrometry analysis of 2-nitrophenylhydrazine carboxy derivatized peptides. J. Am. Soc. Mass Spectrom. 2011, 22, 1958.
9. 13C analysis of amino acids in human hair using trimethylsilyl derivatives and gas chromatography/combustion/isotope ratio mass spectrometry. Rapid Commun. Mass Spectrom. 2013, 27, 1481.
10. M. Miyashita, Y. Hanai, H. Awane, T. Yoshikawa, H. Miyagawa,. Improving peptide fragmentation by N-terminal derivatization with high proton affinity. Rapid Commun. Mass Spectrom. 2011, 25, 1130.
11. S. E. Kulevich, B. L. Frey, G. Kreitinger, L. M. Smith,. Alkylating tryptic peptides to enhance electrospray ionization mass spectrometry analysis. Anal. Chem. 2010, 82, 10135.
12. J. A. Madsen, J. S. Brodbelt,. Simplifying fragmentation patterns of multiply charged peptides by N-terminal derivatization and electron transfer collision activated dissociation. Anal. Chem. 2009, 81, 3645.
13. M. L. Hennrich, P. J. Boersema, H. van den Toorn, N. Mischerikow, A. J. Heck, S. Mohammed,. Effect of chemical modifications on peptide fragmentation behavior upon electron transfer induced dissociation. Anal. Chem. 2009, 81, 7814.
14. G. Chiappetta, S. Ndiaye, E. Demey, I. Haddad, G. Marino, A. Amoresano, J. Vinh,. Dansyl-peptides matrix-assisted laser desorption/ionization mass spectrometric (MALDI-MS) and tandem mass spectrometric (MS/MS) features improve the liquid chromatography/MALDI-MS/MS analysis of the proteome. Rapid Commun. Mass Spectrom. 2010, 24, 3021.
15. J. S. Kim, J. H. Kim, H. J. Kim,. Matrix-assisted laser desorption/ionization signal enhancement of peptides by picolinamidination of amino groups. Rapid Commun. Mass Spectrom. 2008, 22, 495.
16. Y. Xu, L. Zhang, H. Lu, P. Yang,. Mass spectrometry analysis of phosphopeptides after peptide carboxy group derivatization. Anal. Chem. 2008, 80, 8324.
17. L. Zhang, Y. Xu, H. Lu, P. Yang,. Carboxy group derivatization for enhanced electron-transfer dissociation mass spectrometric analysis of phosphopeptides. Proteomics 2009, 9, 4093.
18. X. Qiao, L. Sun, L. Chen, Y. Zhou, K. Yang, Z. Liang, L. Zhang, Y. Zhang,. Piperazines for peptide carboxyl group derivatization: effect of derivatization reagents and properties of peptides on signal enhancement in matrix-assisted laser desorption/ionization mass spectrometry. Rapid Commun. Mass Spectrom. 2011, 25, 639.
19. B. L. Frey, D. T. Ladror, S. B. Sondalle, C. J. Krusemark, A. L. Jue, J. J. Coon, L. M. Smith,. Chemical derivatization of peptide carboxyl groups for highly efficient electron transfer dissociation. J. Am. Soc. Mass Spectrom. 2013, 24, 1710.
20. B. J. Ko, J. S. Brodbelt,. Enhanced electron transfer dissociation of peptides modified at C-terminus with fixed charges. J. Am. Soc. Mass Spectrom. 2012, 23, 1991.
21. J. Leng, H. Wang, L. Zhang, J. Zhang, H. Wang, Y. Guo,. A highly sensitive isotope-coded derivatization method and its application for the mass spectrometric analysis of analytes containing the carboxyl group. Anal. Chim. Acta 2013, 758, 114.
22. N. Mano, S. Aoki, T. Yamazaki, Y. Nagaya, M. Mori, K. Abe, M. Shimada, H. Yamaguchi, T. Goto, J. Goto,. Analysis of phosphorylated peptides by double pseudoneutral loss extraction coupled with derivatization using N-(4-bromobenzoyl)aminoethanethiol. Anal. Chem. 2009, 81, 9395.
23. H. Tsumoto, M. Ra, K. Samejima, R. Taguchi, K. Kohda,. Chemical derivatization of peptides containing phosphorylated serine/threonine for efficient ionization and quantification in matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Rapid Commun. Mass Spectrom. 2008, 22, 965.
24. M. Watanabe, K. Terasawa, K. Kaneshiro, H. Uchimura, R. Yamamoto, Y. Fukuyama, K. Shimizu, T. A. Sato, K. Tanaka,. Improvement of mass spectrometry analysis of glycoproteins by MALDI-MS using 3-aminoquinoline/alpha-cyano-4- hydroxycinnamic acid. Anal. Bioanal. Chem. 2013, 405, 4289.
25. Y. H. Ahn, E. S. Ji, J. Y. Lee, K. Cho, J. S. Yoo,. Arginine-mimic labeling with guanidinoethanethiol to increase mass sensitivity of lysine-terminated phosphopeptides by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Rapid Commun. Mass Spectrom. 2007, 21, 2204.
26. P. Giron, L. Dayon, J. C. Sanchez,. Cysteine tagging for MS-based proteomics. Mass Spectrom. Rev. 2011, 30, 366.
27. J. W. Baty, M. B. Hampton, C. C. Winterbourn,. Proteomic detection of hydrogen peroxide-sensitive thiol proteins in Jurkat cells. Biochem. J. 2005, 389, 785.
28. J. L. Frahm, I. D. Bori, D. L. Comins, A. M. Hawkridge, D. C. Muddiman,. Achieving augmented limits of detection for peptides with hydrophobic alkyl tags. Anal. Chem. 2007, 79, 3989.
29. D. K. Williams, C. W. Meadows, I. D. Bori, A. M. Hawkridge, D. L. Comins, D. C. Muddiman,. Synthesis, characterization, and application of iodoacetamide derivatives utilized for the ALiPHAT strategy. J. Am. Chem. Soc. 2008, 130, 2122.
30. C. M. Shuford, D. L. Comins, J. L. Whitten, J. C. Burnett, D. C. Muddiman,. Improving limits of detection for B-type natriuretic peptide using PC-IDMS: an application of the ALiPHAT strategy. Analyst 2010, 135, 36.
31. M. Zabet-Moghaddam, A. L. Shaikh, S. Niwayama,. Peptide peak intensities enhanced by cysteine modifiers and MALDI TOF MS. J. Mass Spectrom. 2012, 47, 1546.
32. J. Li, H. Ma, X. Wang, S. Xiong, S. Dong, S. Wang,. Enhanced detection of thiol peptides by matrix-assisted laser desorption/ionization mass spectrometry after selective derivatization with a tailor-made quaternary ammonium tag containing maleimidyl group. Rapid Commun. Mass Spectrom. 2007, 21, 2608.
33. L. Vasicek, J. S. Brodbelt,. Enhanced electron transfer dissociation through fixed charge derivatization of cysteines. Anal. Chem. 2009, 81, 7876.
34. T. Shimada, H. Kuyama, T. A. Sato, K. Tanaka,. Development of iodoacetic acid-based cysteine mass tags: detection enhancement for cysteine-containing peptide by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Anal. Biochem. 2012, 421, 785.
35. 2 capture by a task-specific ionic liquid. J. Am. Chem. Soc. 2002, 124, 926.
36. K. Dreisewerd,. The desorption process in MALDI. Chem. Rev. 2003, 103, 395.
37. S. G. Valeja, J. D. Tipton, M. R. Emmett, A. G. Marshall,. New reagents for enhanced liquid chromatographic separation and charging of intact protein ions for electrospray ionization mass spectrometry. Anal. Chem. 2010, 82, 7515.