Improved detection of intact tyrosine sulfate-containing peptides by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry in linear negative ion mode

International Journal of Biochemistry and Cell Biology

Volumn 42, Issue 1, 2010, Pages 174-179

  Drake, Steven K ^a   Hortin, Glen L ^a  

^a NATIONAL INSTITUTES OF HEALTH   (United States)

Author keywords

2 Antiplasmin sulfation; Bioactive peptides; MALDI TOF mass spectrometry; Post translational modification; Tyrosine sulfation

Indexed keywords

ALPHA 2 ANTIPLASMIN; ALPHA CYANO 4 HYDROXYCINNAMIC ACID; CERULETIDE; CHOLECYSTOKININ OCTAPEPTIDE; GENTISIC ACID; HIRUDIN; PEPTIDE; PROTEIN KINASE P60; SINAPIC ACID; TYROSINE SULFATE;

ARTICLE; CONTROLLED STUDY; DESORPTION; IONIZATION; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; PHOSPHORYLATION; PROTEIN PROCESSING; STOICHIOMETRY; SULFATION;

ALPHA-2-ANTIPLASMIN; AMINO ACID SEQUENCE; CHOLECYSTOKININ; MOLECULAR SEQUENCE DATA; PEPTIDES; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; TRYPSIN; TYROSINE;

EID: 70549091167     PISSN: 13572725     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.biocel.2009.10.018     Document Type: Article

References (48)

1. Amano Y., Shinohara H., Sakagami Y., and Matsubayashi Y. Ion-selective enrichment of tyrosine-sulfated peptides from complex protein digests. Anal Biochem 346 (2005) 124-131
2. Balsved D., Bundgaard J.R., and Sen J.W. Stability of tyrosine sulfate in acidic solutions. Anal Biochem 363 (2007) 70-76
3. Bettelheim F.R. Tyrosine O-sulfate in a peptide from fibrinogen. J Am Chem Soc 76 (1954) 2838-2839
4. Brower E.T., Schon A., Klein J.C., and Freire E. Binding thermodynamics of the N-terminal peptide of the CCR5 coreceptor to HIV-1 envelope glycoprotein gp120. Biochemistry 48 (2009) 779-785
5. Christie D.L., Hill R.M., Isakow K., and Barling P.M. Identification of tyrosine O-sulfate in proteins by reverse-phase high-performance liquid chromatography: use of base hydrolysis combined with precolumn derivatization using phenyl isothiocyanate. Anal Biochem 154 (1986) 92-99
6. Costagliola S., Panneels V., Bonomi M., Koch J., Many M.C., Smits G., et al. Tyrosine sulfation is required for agonist recognition by glycoprotein hormone receptors. EMBO J 21 (2002) 504-513
7. Danan L.M., Yu Z.H., Hoffhines A.J., Moore K.L., and Leary J.A. Mass spectrometric kinetic analysis of human tyrosylprotein sulfotransferase-1 and -2. J Am Soc Mass Spectrom 19 (2008) 1459-1466
8. Dong J.F., Li C.Q., and Lopez J.A. Tyrosine sulfation of the glycoprotein Ib-IX complex: identification of sulfated residues and effect on ligand binding. Biochemistry 33 (1994) 13946-13953
9. Farzan M., Vasilieva N., Schnitzler C.E., Chung S., Robinson J., Gerard N.P., et al. Tyrosine sulfation of the amino-terminus of CCR5 facilitates HIV-1 entry. Cell 96 (1999) 667-676
10. Gibson B.W., and Cohen P. Liquid secondary ion mass spectrometry of phosphorylated and sulfated peptides and proteins. Methods Enzymol 193 (1990) 480-501
11. Gregory H., Hardy P.M., Jones D.S., Kenner G.W., and Sheppard R.C. The antral hormone gastrin. Nature 204 (1964) 931-933
12. Hoffhines A.J., Damoc E., Bridges K.G., Leary J.A., and Moore K.L. Detection and purification of tyrosine-sulfated proteins using a novel anti-sulfotyrosine monoclonal antibody. J Biol Chem 281 (2006) 37877-37887
13. Hortin G.L. Sulfation of tyrosine residue in coagulation factor V. Blood 76 (1990) 946-952
14. Hortin G.L. The MALDI TOF mass spectrometric view of the plasma proteome and peptidome. Clin Chem 52 (2006) 1223-1237
15. Hortin G.L., Farries T.C., Graham J.P., and Atkinson J.P. Sulfation of tyrosine residues increases activity of the fourth component of complement. Proc Natl Acad Sci USA 86 (1989) 1338-1342
16. 2-antiplasmin. J Biol Chem 262 (1987) 3082-3085
17. Hortin G., Folz R., Gordon J.I., and Strauss S.W. Characterization of tyrosine sulfation in proteins and criteria for predicting their occurrence. Biochem Biophys Res Commun 141 (1986) 326-333
18. Hortin G.L., Griest T., and Benutto B.M. Separations of sulfated and nonsulfated forms of peptides by capillary electrophoresis: comparison with reversed-phase HPLC. BioChromatography 5 (1990) 118-120
19. Hortin G., Sims H., and Strauss A.W. Identification of the site of sulfation of the fourth component of complement. J Biol Chem 261 (1986) 1786-1793
20. Huang S.C., Yu D.H., Wank S.A., Mantey S., Gardner J.D., and Jensen R.T. Importance of sulfation of gastrin and cholecystokinin (CCK) on affinity for gastrin and CCK receptors. Peptides 10 (1989) 785-789
21. Huttner W.B. Sulphation of tyrosine residues-a widespread modification of proteins. Nature 299 (1982) 273-276
22. Huttner W.B. Determination and occurrence of tyrosine O-sulfate in proteins. Methods Enzymol 107 (1984) 200-223
23. Huttner W.B. Tyrosine sulfation and the secretory pathway. Ann Rev Physiol 50 (1988) 363-376
24. Jenne D., Hille A., Stanley K.K., and Huttner W.B. Sulfation of two tyrosine residues in human complement S-protein (vitronectin). Eur J Biochem 185 (1989) 391-395
25. Karp D.R. Post-translational modification of the fourth component of complement. J Biol Chem 258 (1983) 12745-12748
26. Kehoe J.W., and Bertozzi C.R. Tyrosine sulfation: a modulator of extracellular protein-protein interations. Chem Biol 7 (2000) R57-R61
27. Leyte A., van Schijndel H.B., Niehrs C., Huttner W.B., Verbeet M.P., Mertens K., et al. Sulfation of Tyr1680 of human blood coagulation factor VIII is essential for the interaction of factor VIII with von Willebrand factor. J Biol Chem 266 (1991) 740-746
28. Liu H., and Hakansson K. Electron capture dissociation of tyrosine O-sulfated peptides complexed with divalent metal cations. Anal Chem 78 (2006) 7570-7576
29. Medzihradszky K.F., Darula Z., Perlson E., Fainzilber M., Chalkley R.J., Ball H., et al. O-Sulfonation of serine and threonine: mass spectrometric detection and characterization of a new post-translational modification in diverse proteins throughout the eukaryotes. Mol Cell Proteomics 3 (2004) 429-443
30. Michnick D.A., Pittman D.D., Wise R.J., and Kaufman R.J. Identification of individual tyrosine sulfation sites within factor VIII required for optimal activity and efficient thrombin cleavage. J Biol Chem 269 (1994) 20095-20102
31. Monigatti F., Gasteiger E., Bairoch A., and Jung E. The Sulfinator: predicting tyrosine sulfation sites in protein sequences. Bioinformatics 18 (2002) 769-770
32. Moore K.L. The biology and enzymology of protein tyrosine O-sulfation. J Biol Chem 278 (2003) 24243-24246
33. Monigatti F., Hekking B., and Steen H. Protein sulfation analysis-A primer. Biochim Biophys Acta 1764 (2006) 1904-1913
34. 2 to tyrosine 18 in the activation peptide. J Biol Chem 261 (1986) 4008-4014
35. Nemeth-Cawley J.F., Karnik S., and Rouse J.C. Analysis of sulfated peptides using positive electrospray ionization tandem mass spectrometry. J Mass Spectrom 36 (2001) 1301-1311
36. Onnerfjord P., Heathfield T.F., and Heinegard D. Identification of tyrosine sulfation in extracellular leucine-rich repeat proteins using mass spectrometry. J Biol Chem 279 (2004) 26-33
37. Paul J.I., and Hynes R.O. Multiple fibronectin subunits and their post-translational modifications. J Biol Chem 259 (1984) 13477-13487
38. Petricoin E.F., Belluco C., Araujo R.P., and Liotta L.A. The blood peptidome: a higher dimension of information content for cancer biomarker discovery. Nat Rev Cancer 6 (2006) 961-967
39. Pouyani T., and Seed B. PSGL-1 recognition of P-selectin is controlled by a tyrosine sulfation consensus at the PSGL-1 amino-terminus. Cell 83 (1995) 333-343
40. Rappsilber J., Steen H., and Mann M. Labile sulfogroup allows differentiation of sulfotyrosine and phosphotyrosine in peptides. J Mass Spectrom 36 (2001) 832-833
41. Salek M., Costagliola S., and Lehmann W.D. Protein tyrosine O-sulfation analysis by exhaustive product ion scanning with minimum collision offset in a NanoESI Q-TOF tandem mass spectometer. Anal Chem 76 (2004) 5136-5142
42. Seibert C., and Sakmar T.P. Toward a framework for sulfoproteomics: synthesis and characterization of sulfotyrosine-containing peptides. Biopolymers 90 (2008) 459-477
43. Talbo G., and Roepstorff P. Determination of sulfated peptides via prompt fragmentation by UV matrix-assisted laser desorption/ionization mass spectrometry. Rapid Commun Mass Spectrom 7 (1993) 201-204
44. Wolfender J.L., Chu F., Ball H., Wolfender F., Fainzilber M., Baldwin M.A., et al. Identification of tyrosine sulfation in Conus pennaceus conotoxins a-PnIA and a-PnIB: Further investigation of labile sulfo- and phosphopeptides by electrospray, matrix-assisted laser desorption/ionization (MALDI) and atmospheric pressure MALDI mass spectrometry. J Mass Spectrom 34 (1999) 447-454
45. Woods A.S., Wang H.Y.J., and Jackson S.N. Sulfation, the up-and-coming post-translational modification: its role and mechanism in protein-protein interaction. J Proteome Res 6 (2007) 1176-1182
46. Xu C., Sui J., Tao H., Zhu Q., and Marasco W.A. Human anti-CXCR4 antibodies undergo VH replacement, exhibit functional V-region sulfation, and define CXCR4 antigenic heterogeneity. J Immunol 179 (2007) 2408-2418
47. Yagami T., Kitagawa K., Aida C., Fujiwara H., and Futaki S. Stabilization of tyrosine O-sulfate residue by cationic functional group: formation of a conjugate acid-base pair. J Peptide Res 56 (2000) 239-249
48. Yu Y., Hoffhines A.J., Moore K.L., and Leary J.A. Determination of the sites of tyrosine O-sulfation in peptides and proteins. Nat Methods 4 (2007) 583-588