Picolinamidination of Phosphopeptides for MALDI-TOF-TOF Mass Spectrometric Sequencing with Enhanced Sensitivity

Journal of the American Society for Mass Spectrometry

Volumn 20, Issue 9, 2009, Pages 1751-1758

  Kim, Jong Seo ^a   Cui, Enshi ^a   Kim, Hie Joon ^a  

^a Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE GROUPS; ENHANCED SENSITIVITY; ION SERIES; LYSINE RESIDUES; MALDI-TOF/TOF; MASS SPECTROMETRIC SEQUENCING; MATRIX ASSISTED LASER DESORPTION/IONIZATION; N-TERMINALS; NEGATIVE CHARGE; ORDERS OF MAGNITUDE; PHOSPHATE GROUP; PHOSPHOPEPTIDES; PHOSPHORYLATION SITES; POSITIVE ION MODE; SIGNAL ENHANCEMENT;

AMINO ACIDS; DESORPTION; ORGANIC COMPOUNDS; PEPTIDES; PHOSPHORYLATION;

AMINES;

PHOSPHOPEPTIDE; PICOLINAMIDE;

AMINO ACID SEQUENCE; AMINO TERMINAL SEQUENCE; ARTICLE; CONTROLLED STUDY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; PROTEIN MODIFICATION; PROTEIN PHOSPHORYLATION; SIGNAL DETECTION; TANDEM MASS SPECTROMETRY;

AMIDES; MICROCHEMISTRY; PEPTIDE MAPPING; PHOSPHOPEPTIDES; SEQUENCE ANALYSIS, PROTEIN; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION;

EID: 69549088128     PISSN: 10440305     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jasms.2009.05.016     Document Type: Article

References (36)

1. Janek K., Wenschuh H., Bienert M., and Krause E. Phosphopeptide Analysis by Positive and Negative Ion Matrix-Assisted Laser Desorption/Ionization Mass Spectrometry. Rapid Commun. Mass Spectrom 15 (2001) 1593-1599
2. Ma Y., Lu Y., Zeng H., Ron D., Mo W., and Neubert T.A. Characterization of Phosphopeptides from Protein Digests Using Matrix-Assisted Laser Desorption/Ionization Time-of-Flight Mass Spectrometry and Nanoelectrospray Quadrupole Time-of-Flight Mass Spectrometry. Rapid Commun. Mass Spectrom 15 (2001) 1693-1700
3. Kjellstrom S., and Jensen O.N. Phosphoric Acid as a Matrix Additive for MALDI MS Analysis of Phosphopeptides and Phosphoproteins. Anal. Chem 76 (2004) 5109-5117
4. Pashkova A., Moskovets E., and Karger B.L. Coumarin Tags for Improved Analysis of Peptides by MALDI-TOF MS and MS/MS. 1. Enhancement in MALDI MS Signal Intensities. Anal. Chem 76 (2004) 4550-4557
5. Yang X., Wu H., Kobayashi T., Solaro R.J., and van Breemen R.B. Enhanced Ionization of Phosphorylated Peptides during MALDI TOF Mass Spectrometry. Anal. Chem 76 (2004) 1532-1536
6. Xu C.F., Lu Y., Ma J., Mohammadi M., and Neubert T.A. Identification of Phosphopeptides by MALDI Q-TOF MS in Positive and Negative Ion Modes After Methyl Esterification. Mol. Cell. Proteom 4 (2005) 809-818
7. Juhasz P., and Biemann K. Mass Spectrometric Molecular-Weight Determination of Highly Acidic Compounds of Biological Significance Via Their Complexes with Basic Polypeptides. Proc. Natl. Acad. Sci. U.S.A. 91 (1994) 4333-4337
8. Carr S.A., Huddleston M.J., and Annan R.S. Selective Detection and Sequencing of Phosphopeptides at the Femtomole Level by Mass Spectrometry. Anal. Biochem 239 (1996) 180-192
9. Posewitz M.C., and Tempst P. Immobilized Gallium(III) Affinity Chromatography of Phosphopeptides. Anal. Chem 71 (1999) 2883-2892
10. Raska C.S., Parker C.E., Dominski Z., Marzluff W.F., Glish G.L., Pope R.M., and Borchers C.H. Direct MALDI-MS/MS of Phosphopeptides Affinity-Bound to Immobilized Metal Ion Affinity Chromatography Beads. Anal. Chem 74 (2002) 3429-3433
11. Liu H., Stupak J., Zheng J., Keller B.O., Brix B.J., Fliegel L., and Li L. Open Tubular Immobilized Metal Ion Affinity Chromatography Combined with MALDI MS and MS/MS for Identification of Protein Phosphorylation Sites. Anal. Chem 76 (2004) 4223-4232
12. Kokubu M., Ishihama Y., Sato T., Nagasu T., and Oda Y. Specificity of Immobilized Metal Affinity-Based IMAC/C18 Tip Enrichment of Phosphopeptides for Protein Phosphorylation Analysis. Anal. Chem 77 (2005) 5144-5154
13. Dunn J.D., Watson J.T., and Bruening M.L. Detection of Phosphopeptides Using Fe(III)-Nitrilotriacetate Complexes Immobilized on a MALDI Plate. Anal. Chem 78 (2006) 1574-1580
14. Pan C., Ye M., Liu Y., Feng S., Jiang X., Han G., Zhu J., and Zou H. Enrichment of Phosphopeptides by Fe3+-Immobilized Mesoporous Nanoparticles of MCM-41 for MALDI and Nano-LC-MS/MS Analysis. J. Proteome Res 5 (2006) 3114-3124
15. Chen C.-T., and Chen Y.-C. Fe3O4/TiO2 Core/Shell Nanoparticles as Affinity Probes for the Analysis of Phosphopeptides Using TiO2 Surface-Assisted Laser Desorption/Ionization Mass Spectrometry. Anal. Chem 77 (2005) 5912-5919
16. Larsen M.R., Thingholm T.E., Jensen O.N., Roepstorff P., and Jorgensen T.J. Highly Selective Enrichment of Phosphorylated Peptides from Peptide Mixtures Using Titanium Dioxide Microcolumns. Mol. Cell. Proteom 4 (2005) 873-886
17. Schmidt A., Csaszar E., Ammerer G., and Mechtler K. Enhanced Detection and Identification of Multiply Phosphorylated Peptides Using TiO2 Enrichment in Combination with MALDI TOF/TOF MS. Proteomics 8 (2008) 4577-4592
18. Ficarro S.B., Parikh J.R., Blank N.C., and Marto J.A. Niobium(V) Oxide (Nb2O5): Application to Phosphoproteomics. Anal. Chem 80 (2008) 4606-4613
19. Li Y., Lin H., Deng C., Yang P., and Zhang X. Highly Selective and Rapid Enrichment of Phosphorylated Peptides Using Gallium Oxide-Coated Magnetic Microspheres for MALDI-TOF-MS and Nano-LC-ESI-MS/MS/MS Analysis. Proteomics 8 (2008) 238-249
20. Oda Y., Nagasu T., and Chait B.T. Enrichment Analysis of Phosphorylated Proteins as a Tool for Probing the Phosphoproteome. Nat. Biotechnol 19 (2001) 379-382
21. Zhou H., Watts J.D., and Aebersold R. A Systematic Approach to the Analysis of Protein Phosphorylation. Nat. Biotechnol 19 (2001) 375-378
22. Goshe M.B., Veenstra T.D., Panisko E.A., Conrads T.P., Angell N.H., and Smith R.D. Phosphoprotein Isotope-Coded Affinity Tags: Application to the Enrichment and Identification of Low-Abundance Phosphoproteins. Anal. Chem 74 (2002) 607-616
23. McLachlin D.T., and Chait B.T. Improved β-Elimination-Based Affinity Purification Strategy for Enrichment of Phosphopeptides. Anal. Chem 75 (2003) 6826-6836
24. Qian W.-J., Goshe M.B., Camp D.G., Yu L.-R., Tang K., and Smith R.D. Phosphoprotein Isotope-Coded Solid-Phase Tag Approach for Enrichment and Quantitative Analysis of Phosphopeptides from Complex Mixtures. Anal. Chem 75 (2003) 5441-5450
25. Jalili P.R., Sharma D., and Ball H.L. Enhancement of Ionization Efficiency and Selective Enrichment of Phosphorylated Peptides from Complex Protein Mixtures Using a Reversible Poly-Histidine tag. J. Am. Soc. Mass Spectrom 18 (2007) 1007-1017
26. Klemm C., Schroder S., Gluckmann M., Beyermann M., and Krause E. Derivatization of Phosphorylated Peptides with S- and N-Nucleophiles for Enhanced Ionization Efficiency in Matrix-Assisted Laser Desorption/Ionization Mass Spectrometry. Rapid Commun. Mass Spectrom 18 (2004) 2697-2705
27. Amoresano A., Monti G., Cirulli C., and Marino G. Selective Detection and Identification of Phosphopeptides by Dansyl MS/MS/MS Fragmentation. Rapid Commun. Mass Spectrom 20 (2006) 1400-1404
28. Arrigoni G., Resjo S., Levander F., Nilsson R., Degerman E., Quadroni M., Pinna L.A., and James P. Chemical Derivatization of Phosphoserine and Phosphothreonine Containing Peptides to Increase Sensitivity for MALDI-Based Analysis and for Selectivity of MS/MS Analysis. Proteomics 6 (2006) 757-766
29. Ahn Y.H., Ji E.S., Lee J.Y., Cho K., and Yoo J.S. 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 21 (2007) 2204-2210
30. Li H., and Sundararajan N. Charge Switch Derivatization of Phosphopeptides for Enhanced Surface-Enhanced Raman Spectroscopy and Mass Spectrometry Detection. J. Proteome Res 6 (2007) 2973-2977
31. Asara J.M., and Allison J. Enhanced Detection of Phosphopeptides in Matrix-Assisted Laser Desorption/Ionization Mass Spectrometry Using Ammonium Salts. J. Am. Soc. Mass Spectrom 10 (1999) 35-44
32. Kim J.-S., Kim J.-H., and Kim H.-J. Matrix-Assisted Laser Desorption/Ionization Signal Enhancement of Peptides by Picolinamidination of Amino Groups. Rapid Commun. Mass Spectrom 22 (2008) 495-502
33. Weintraub L., Oles S.R., and Kalish N. Convenient General Synthesis of Amidines. J. Org. Chem 33 (1968) 1679-1681
34. Kim J.-S., Kim J.-Y., and Kim H.-J. Suppression of Matrix Clusters and Enhancement of Peptide Signals in MALDI-TOF Mass Spectrometry Using Nitrilotriacetic Acid. Anal. Chem 77 (2005) 7483-7488
35. Beardsley R.L., and Reilly J.P. Fragmentation of Amidinated Peptide Ions. J. Am. Soc. Mass Spectrom 15 (2004) 158-167
36. Beardsley R.L., Sharon L.A., and Reilly J.P. Peptide De Novo Sequencing Facilitated by a Dual-Labeling Strategy. Anal. Chem 77 (2005) 6300-6309