Mapping protein cysteine sulfonic acid modifications with specific enrichment and mass spectrometry: An integrated approach to explore the cysteine oxidation

Proteomics

Volumn 10, Issue 16, 2010, Pages 2961-2971

  Chang, Yuan Chang ^a,b   Huang, Chien Ning ^c   Lin, Chia Hung ^b   Chang, Huan Cheng ^a,b   Wu, Chih Che ^c  

^a INSTITUTE OF ATOMIC AND MOLECULAR SCIENCES   (Taiwan)

^b NATIONAL TAIWAN NORMAL UNIVERSITY   (Taiwan)

^c NATIONAL CHI NAN UNIVERSITY   (Taiwan)

Author keywords

Affinity purification; MALDI MS; Performic acid oxidation; Protein cysteine sulfonic acid modification; Technology

Indexed keywords

CYSTEIC ACID; CYSTEINE; PHOSPHOPEPTIDE; POLYARGININE;

ARTICLE; COMPLEX FORMATION; MASS SPECTROMETRY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; OXIDATION; PH; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN MODIFICATION; SENSITIVITY ANALYSIS;

AMINO ACID SEQUENCE; CHROMATOGRAPHY, AFFINITY; CYSTEINE; DIAMOND; FORMIC ACIDS; HYDROGEN-ION CONCENTRATION; INSULIN; NANOSTRUCTURES; OXIDATION-REDUCTION; PEPTIDE FRAGMENTS; PEPTIDE MAPPING; PEPTIDES; PHOSPHOPEPTIDES; SENSITIVITY AND SPECIFICITY; SERUM ALBUMIN, BOVINE; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; SULFONIC ACIDS; TRYPSIN;

EID: 77955640917     PISSN: 16159853     EISSN: 16159861     Source Type: Journal    
DOI: 10.1002/pmic.200900850     Document Type: Article

References (42)

1. Wood, Z. A., Poole, L. B., Karplus, P. A., Peroxiredoxin evolution and the regulation of hydrogen peroxide signaling. Science 2003, 300, 650-653. (Pubitemid 36520591)
2. 2, a necessary evil for cell signaling. Science 2006, 312, 1882-1883.
3. Giles, G. I., The redox regulation of thiol dependent signaling pathways in cancer. Curr. Pharm. Des. 2006, 12, 4427-4443.
4. Winterbourn, C. C., Hampton, M. B., Thiol chemistry and specificity in redox signaling. Free Radic. Biol. Med. 2008, 45, 549-561.
5. Reddie, K. G., Carroll, K. S., Expanding the functional diversity of proteins through cysteine oxidation. Curr. Opin. Chem. Biol. 2008, 12, 746-754.
6. Rhee, S. G., Chae, H. Z., Kim, K., Peroxiredoxins: A historical overview and speculative preview of novel mechanisms and emerging concepts in cell signaling. Free Radic. Biol. Med. 2005, 38, 1543-1552. (Pubitemid 40726061)
7. Wood, Z. A., Schröer, E., Robin Harris, J., Poole, L. B., Structure, mechanism and regulation of peroxiredoxins. Trends Biochem. Sci. 2003, 28, 32-40.
8. Rabilloud, T., Heller, M., Gasnier, F., Luche, S. et al., Proteomics analysis of cellular response to oxidative stress. J. Biol. Chem. 2002, 277, 19396-19401.
9. Cross, J. V., Templeton, D. J., Regulation of signal transduction through protein cysteine oxidation. Antiox. Redox signal. 2006, 8, 1819-1827.
10. Jonsson, T. J., Johnson, L. C., Lowther, W. T., Structure of the sulphiredoxin-peroxiredoxin complex reveals an essential repair embrace. Nature 2008, 451, 98-101.
11. Cabiscol, E., Ros, J., in: Dalle-Donne, I., Scaloni, A., Butterfield, A. (Ed.), Redox Proteomics, Wiley-Interscience, Hoboken 2006, pp. 399-471.
12. Wagner, E., Luche, S., Penna, L., Chevallet, M. et al., A method for detection of overoxidation of cysteines: peroxiredoxins are oxidized in vivo at the active-site cysteine during oxidative stress. Biochem. J. 2002, 366, 777-785.
13. Lim, J. C., Choi, H. I., Park, Y. S., Nam, H. W. et al., Irreversible oxidation of the active-site cysteine of peroxiredoxin to cysteine sulfonic acid for enhanced molecular chaperone activity. J. Biol. Chem. 2008, 283, 28873-28880.
14. Temporini, C., Calleri, E., Massolini, G., Caccialanza, G., Integrated analytical strategies for the study of phosphorylation and glycosylation in proteins. Mass Spectrom. Rev. 2008, 27, 207-236. (Pubitemid 351547982)
15. Karas, M., Hillenkamp, F., Laser desorption ionization of proteins with molecular masses exceeding 10,000 daltons. Anal. Chem. 2002, 60, 2299-2301.
16. Tanaka, K., Waki, H., Ido, Y., Akita, S. et al., Protein and polymer analyses up to m/z 100 000 by laser ionization time-of-flight mass spectrometry. Rapid Commun. Mass Spectrom. 1988, 2, 151-153.
17. Reinders, J., Lewandrowski, U., Moebius, J., Wagner, Y., Sickmann, A., Challenges in mass spectrometry-based proteomics. Proteomics 2004, 4, 3686-3703.
18. Witze, E. S., Old, W. M., Resing, K. A., Ahn, N. G., Mapping protein post-translational modifications with mass spectrometry. Nat. Methods 2007, 4, 798-806. (Pubitemid 350055576)
19. Pan, C. S., Xu, S. Y., Zhou, H. J., Fu, Y. et al., Recent developments in methods and technology for analysis of biological samples by MALDI-TOF-MS. Anal. Bioanal. Chem. 2007, 387, 193-204. (Pubitemid 44956272)
20. Jiang, X., Ye, M., Zou, H., Technologies and methods for sample pretreatment in efficient proteome and peptidome analysis. Proteomics 2008, 8, 686-705. (Pubitemid 351362930)
21. Thingholm, T. E., Jensen, O. N., Larsen, M. R., Analytical strategies for phosphoproteomics. Proteomics 2009, 9, 1451-1468.
22. Banoub, J. H., Newton, R. P., Esmans, E., Ewing, D. F., Mackenzie, G., Recent developments in mass spectrometry for the characterization of nucleosides, nucleotides, oligonucleotides, and nucleic acids. Chem. Rev. 2005, 105, 1869-1915. (Pubitemid 40773670)
23. Kong, X. L., Huang, L. C., Hsu, C.M., Chen, W. H. et al., High-affinity capture of proteins by diamond nanoparticles for mass spectrometric analysis. Anal. Chem. 2005, 77, 259-265. (Pubitemid 40096694)
24. Kinumi, T., Shimomae, Y., Arakawa, R., Tatsu, Y. et al., Effective detection of peptides containing cysteine sulfonic acid using matrix-assisted laser desorption/ionization and laser desorption/ionization on porous silicon mass spectrometry. J. Mass Spectrom. 2006, 41, 103-112. (Pubitemid 43164841)
25. Juhasz, P., Biemann, K., Mass spectrometric molecular-weight determination of highly acidic compounds of biological significance via their complexes with basic polypeptides. Proc. Natl. Acad. Sci. USA 1994, 91, 4333-4337. (Pubitemid 24143427)
26. Leitner, A., Lindner, W., Chemistry meets proteomics: The use of chemical tagging reactions for MS-based proteomics. Proteomics 2006, 6, 5418-5434. (Pubitemid 44683212)
27. Charles, R. L., Schroder, E., May, G., Free, P. et al., Protein sulfenation as a redox sensor: proteomics studies using a novel biotinylated dimedone analogue. Mol. Cell. Proteomics 2007, 6, 1473-1484. (Pubitemid 47506161)
28. Woo, H. A., Kang, S. W., Kim, H. K., Yang, K. S. et al., Reversible oxidation of the active site cysteine of peroxiredoxins to cysteine sulfinic acid. Immunoblot detection with antibodies specific for the hyperoxidized cysteine-containing sequence. J. Biol. Chem. 2003, 278, 47361-47364.
29. Lee, Y. H., Shin, J. W., Ryu, S., Lee, S. W. et al., Enrichment of N-terminal sulfonated peptides by a water-soluble fullerene derivative and its applications to highly efficient proteomics. Anal. Chim. Acta 2006, 556, 140-144. (Pubitemid 43042586)
30. Chang, C.-K., Wu, C.-C., Wang, Y.-S., Chang, H.-C., Selective extraction and enrichment of multiphosphorylated peptides using polyarginine-coated diamond nanoparticles. Anal. Chem. 2008, 80, 3791-3797.
31. Schug, K. A., Lindner, W., Noncovalent binding between guanidinium and anionic groups: focus on biological- and synthetic-based arginine/guanidinium interactions with phosph[on]ate and sulf[on]ate residues. Chem. Rev. 2005, 105, 67-114.
32. Matulis, D., Lovrien, R., 1-Anilino-8-naphthalene sulfonate anion-protein binding depends primarily on ion pair formation. Biophys. J. 1998, 74, 422-429. (Pubitemid 28041769)
33. Keough, T., Youngquist, R. S., Lacey, M. P., Sulfonic acid derivatives for peptide sequencing by MALDI MS. Anal. Chem. 2003, 75, 156A-165A. (Pubitemid 36512588)
34. Matthiesen, R., Bauw, G., Welinder, K. G., Use of performic acid oxidation to expand the mass distribution of tryptic peptides. Anal. Chem. 2004, 76, 6848-6852. (Pubitemid 39600855)
35. Conrotto, P., Hellman, U., Sulfonation chemistry as a powerful tool for MALDI TOF/TOF de novo sequencing and post-translational modification analysis. J. Biomol. Tech. 2005, 16, 441-452.
36. Samgina, T. Y., Artemenko, K. A., Gorshkov, V. A., Poljakov, N. B., Lebedev, A. T., Oxidation versus carbox-amidomethylation of S-S bond in ranid frog peptides: pro and contra for de novo MALDI-MS sequencing. J. Am. Soc. Mass Spectrom. 2008, 19, 479-487.
37. Dai, J., Wang, J., Zhang, Y., Lu, Z. et al., Enrichment and identification of cysteine-containing peptides from tryptic digests of performic oxidized proteins by strong cation exchange LC and MALDI-TOF/TOF MS. Anal. Chem. 2005, 77, 7594-7604. (Pubitemid 41746226)
38. Dai, J., Zhang, Y., Wang, J., Li, X. et al., Identification of degradation products formed during performic oxidation of peptides and proteins by high-performance liquid chromatography with matrix-assisted laser desorption/ionization and tandem mass spectrometry. Rapid Commun. Mass Spectrom. 2005, 19, 1130-1138.
39. Chen, W. H., Lee, S. C., Sabu, S., Fang, H. C. et al., Solid-phase extraction and elution on diamond (SPEED): a fast and general platform for proteome analysis with mass spectrometry. Anal. Chem. 2006, 78, 4228-4234.
40. Nguyen, T. T.-B., Chang, H.-C., Wu, V. W.-K., Adsorption and hydrolytic activity of lysozyme on diamond nanocrystallites. Diam. Relat. Mater. 2007, 16, 872-876.
41. Lasseter, T. L., Clare, B. H., Abbott, N. L., Hamers, R. J., Covalently modified silicon and diamond surfaces: resistance to nonspecific protein adsorption and optimization for biosensing. J. Am. Chem. Soc. 2004, 126, 10220-10221.
42. Kokubu, M., Ishihama, Y., Sato, T., Nagasu, T., Oda, Y., Specificity of immobilized metal affinity-based IMAC/C18 tip enrichment of phosphopeptides for protein phosphorylation analysis. Anal. Chem. 2005, 77, 5144-5154.