Development of a new method using HILIC-tandem mass spectrometry for the characterization of O-sialoglycopeptides from proteolytically digested caseinomacropeptide

Proteomics

Volumn 10, Issue 20, 2010, Pages 3699-3711

  Hernandez Hernandez, Oswaldo ^a   Lebron Aguilar, Rosa ^b   Quintanilla Lopez, Jesus Eduardo ^a   Sanz, Maria Luz ^a   Moreno, Francisco Javier ^c  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

^b INSTITUTO DE QUÍMICA FÍSICA ROCASOLANO   (Spain)

^c CSIC   (Spain)

Author keywords

Caseinomacropeptide; Glycoproteomics; HILIC ESI MSn; Ion trap; O glycosylation

Indexed keywords

ALANYLVALYLGLUTAMYLSERYLTHREONYLVALYLALANYLTHREONYLLEUCINE; ASPARAGINYLGLUTAMINYLASPARTYLLYSYLTHREONYLGLUTAMYLISOLEUCYLPROLYLTHREONYLISOLEUCYLASPARAGINE; CARBOHYDRATE; CASEINOMACROPEPTIDE; CYSTEINYLTHREONYLSERYLTHREONYLALANYLVALINE; GLYCAN; GLYCOPEPTIDE; ISOLEUCYLGLUTAMYLALANYLVALYLGLUTAMYLSERYLTHREONYLVALYLALANYLTHREONYLLEUCINE; O SIALOGLYCOPEPTIDE; PROLYLTHREONYLTHREONYLGLUTAMYLALANYLVALYLGLUTAMYLSERYLTHREONINE; SERYLTHREONYLPROLYLTHREONYLISOLEUCYLGLUTAMIC ACID; SERYLTHREONYLVALYLALANINE; SIALIC ACID; THREONYLGLUTAMYLISOLEUCYLPROLYLTHREONYLISOLEUCYLASPARAGINE; THREONYLISOLEUCYLALANYLSERYLGLYCYLGLUTAMYLPROLYLTHREONYLSERYLTHREONYLPROLYLTHREONINE; THREONYLISOLEUCYLALANYLSERYLGLYCYLGLUTAMYLPROLYLTHREONYLSERYLTHREONYLPROLYLTHREONYLTHREONYLGLUTAMIC ACID; THREONYLVALYLGLUTAMINYLVALYLTHREONYLSERYLTHREONYLALANYLVALINE; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ARTICLE; CHEMICAL BOND; GLYCOSYLATION; HYDROPHILIC INTERACTION LIQUID CHROMATOGRAPHY ELECTROSPRAY MASS SPECTROMETRY; IONIZATION; MASS SPECTROMETER; MASS SPECTROMETRY; PEPTIDE ANALYSIS; PH; PRIORITY JOURNAL; PROTEOMICS;

AMINO ACID SEQUENCE; ANIMALS; CASEINS; CATTLE; GLYCOSYLATION; MOLECULAR SEQUENCE DATA; PEPTIDE FRAGMENTS; SIALOGLYCOPROTEINS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SWINE; TANDEM MASS SPECTROMETRY;

EID: 78649434468     PISSN: 16159853     EISSN: 16159861     Source Type: Journal    
DOI: 10.1002/pmic.201000156     Document Type: Article

References (42)

1. Vance, B. A., Wu, W., Ribaudo, R., Segal, D. M. et al., CD69 heterogeneity results from usage of both typical (N-X-T) and atypical (N-X-C) N-linked glycosylation motifs. J. Allergy Clin. Immunol. 1997, 99, 1869-1869.
2. Seipert, R. R., Dodds, E. D., Lebrilla, C. B., Exploiting differential dissociation chemistries of O-linked glycopeptide ions for the localization of mucin-type protein glycosylation. J. Proteome Res. 2009, 8, 493-501.
3. Abd El-Salam, M. H., El-Shibini, S., Buchheim, W., Characteristics and potential uses of the casein macropeptide. Int. Dairy J. 1996, 6, 327-341.
4. Manso, M. A., López-Fandiño, R., κ-casein macropeptides from cheese whey: physicochemical, biological, nutritional, and technological features for possible uses. Food Rev. Int. 2004, 20, 329-355.
5. Thom.a-Worringer, C., Sørensen, J., López-Fandiño, R., Health effects and technological features of caseinomacropeptide. Int. Dairy J. 2006, 16, 1324-1333.
6. Dziuba, J., Minkiewicz, P., Influence of glycosylation on micelle-stabilizing ability and biological properties of C-terminal fragments of cow's κ-casein. Int. Dairy J. 1996, 6, 1017-1044.
7. Vreeman, H. J., Visser, S., Slangen, C. J., van Riel, J. A. M., Characterization of bovine κ-casein fractions and the kinetics of chymosin-induced macropeptide release from carbohydrate-free and carbohydrate containing fractions determined by high performance gel permeation chromatography. Biochem. J. 1986, 240, 87-97.
8. Saito, T., Itoh, T., Variations and distributions of O-glycosidically linked sugar chains in bovine κ-casein A. J. Dairy Sci. 1992, 75, 1768-1774.
9. Alpert, A. J., Hydrophilic-Interaction chromatography for the separation of peptides, nucleics-acids and other polar compounds. J. Chromatogr. 1990, 499, 177-196.
10. Alpert, A. J., Shukla, M., Shukla, A. K., Zieske, L. R. et al., Hydrophilic-interaction chromatography of complex carbohydrates. J. Chromatogr. A 1994, 676, 191-202.
11. Guo, Y., Huang, A. H., A HILIC method for the analysis of tromethamine as the counter ion in an investigational pharmaceutical salt. J. Pharm. Biomed. Anal. 2003, 31, 1191-1201.
12. Guo, Y., Gaiki, S., Retention behavior of small polar compounds on polar stationary phases in hydrophilic interaction chromatography. J. Chromatogr. A 2005, 1074, 71-80.
13. Godejohann, M., Hydrophilic interaction chromatography coupled to nuclear magnetic resonance spectroscopy and mass spectroscopy - A new approach for the separation and identification of extremely polar analytes in bodyfluids. J. Chromatogr. A 2007, 1156, 87-93.
14. McCalley, D. V., Study of the selectivity, retention mechanisms and performance of alternative silica-based stationary phases for separation of ionised solutes in hydrophilic interaction chromatography. J. Chromatogr. 2010, 1217, 3408-3417.
15. Hemstrom, P., Irgum, K., Hydrophilic interaction chromatography. J. Sep. Sci. 2006, 29, 784-1821.
16. Berthod, A., Chang, S. S. C., Kullman, J. P. S., Armstrong, D. W., Practice and mechanism of HPLC oligosaccharide separation with a cyclodextrin bonded phase. Talanta 1998, 47, 1001-1012.
17. Hao, Z. G., Xiao, B. M., Weng, N. D., Impact of column temperature and mobile phase components on selectivity of hydrophilic interaction chromatography (HILIC). J. Sep. Sci. 2008, 31, 1449-1464.
18. Wuhrer, M., Koeleman, C. A. M., Hokke, C. H., Deelder, A. M., Protein glycosylation analyzed by normal-phase nano-liquid chromatography-mass spectrometry of glycopeptides. Anal. Chem. 2005, 77, 886-894.
19. Takegawa, Y., Deguchi, K., Ito, H., Keira, T. et al., Simple separation of isomeric sialylated N-glycopeptides by a zwitterionic type of hydrophilic interaction chromatography. J. Sep. Sci. 2006, 29, 2533-2540.
20. Takegawa, Y., Deguchi, K., Ito, H., Keira, T. et al., Separation of isomeric 2-aminopyridine derivatized N-glycans and Nglycopeptides of human serum immunoglobulin G by using a zwitterionic type of hydrophilic-interaction chromatography. J. Chromatogr. A 2006, 1113, 177-181.
21. Takegawa, Y., Hato, M., Deguchi, K., Nakagawa, H. et al., Chromatographic deuterium isotope effects of derivatized N-glycans and N-glycopeptides in a zwitterionic type of hydrophilic interaction chromatography. J. Sep. Sci. 2008, 31, 1594-1597.
22. Picariello, G., Ferranti, P., Mamone, G., Roepstorff, P. et al., Identification of N-linked glycoproteins in human milk by hydrophilic interaction liquid chromatography and mass spectrometry. Proteomics 2008, 8, 3833-3847.
23. Espinosa, S., Bosch, E., Roses, M., Retention of ionizable compounds on HPLC. 5. pH scales and the retention of acids and bases with acetonitrile-water mobile phases. Anal. Chem. 2000, 72, 5193-5200.
24. a) in acetonitrile/water mixtures at various compositions and temperatures. Anal. Chem. 2007, 79, 3180-3187.
25. Yang, Y. Z., Boysen, R. I., Hearn, M. T. W., Hydrophilic interaction chromatography coupled to electrospray mass spectrometry for the separation of peptides and protein digests. J. Chromatogr. A 2009, 1216, 5518-5524.
26. Yoshida, T., Peptide separation by Hydrophilic-Interaction Chromatography: a review. J. Biochem. Biophys. Methods 2004, 60, 265-280.
27. Boersema, P. J., Divecha, N., Heck, A. J. R., Mohammed, S., Evaluation and optimization of ZIC-HILIC-RP as an alternative MudPIT strategy. J. Proteome Res. 2007, 6, 937-946.
28. Scheinthal, B. M., Bettelheim, F. A., Multiple forms of sialic acids. Carbohydr. Res. 1968, 6, 257-265.
29. Domon, B., Costello, C. E., A systematic nomenclature for carbohydrate fragmentations in FAB-MS MS spectra of glycoconjugates. Glycoconj. J. 1988, 5, 397-409.
30. Roepstorff, P., Fohlman, J., Proposal for a common nomenclature for sequence ions in mass-spectra of peptides. Biomed. Mass Spectrom. 1984, 11, 601-601.
31. Holland, J. W., Deeth, H., Alewood, P. F., Proteomic analysis of κ-casein micro-heterogeneity. Proteomics 2004, 4, 743-752.
32. Holland, J. W., Deeth, H., Alewood, P. F., Analysis of Oglycosylation site occupancy in bovine κ-casein glycoforms separated by two dimensional gel electrophoresis. Proteomics 2005, 5, 990-1002.
33. Mollé, D., Léonil, J., Heterogeneity of the bovine κ-casein caseinomacropeptide, resolved by liquid chromatography on-line with electrospray ionization mass spectrometry. J. Chromatogr. A 1995, 708, 223-230.
34. Moreno, F. J., Recio, I., Olano, A., Lopez-Fandino, R., Chromatographic characterization of ovine κ-casein macropeptide. J. Dairy Res. 2000, 67, 349-359.
35. Moreno, F. J., Recio, I., Olano, A., Lopez-Fandino, R., Heterogeneity of caprine κ-casein macropeptide. J. Dairy Res. 2001, 68, 197-208.
36. Pisano, A., Packer, N. H., Redmond, J. W., Williams, K. L. et al., Characterization of O-linked glycosylation motifs in the glycopeptides domain of bovine kappa-casein. Glycobiology 1994, 4, 837-844.
37. n spectra of glycopeptides with neutral and sialylated N-glycans. Rapid Commun. Mass Spectrom. 2006, 20, 741-746.
38. Hunt, D. F., Yates, J. R., Shabanowitz, J., Winston, S. et al., Protein sequencing by tandem mass-spectrometry. Proc. Natl. Acad. Sci. USA 1986, 83, 6233-6237.
39. Vaisar, T., Urban, J., Probing the proline effect in CID of protonated peptides. J. Mass Spectrom. 1996, 31, 1185-1187.
40. 17+ ions of human hemoglobin β-chain. Anal. Chem. 2000, 72, 899-907.
41. Medzihradszky, K. F., Gillece-Castro, B. L., Townsend, R. R., Burlingame, A. L. et al., Structural elucidation of O-linked glycopeptides by high energy collision-induced dissociation. J. Am. Soc. Mass Spectrom. 1996, 7, 319-328.
42. Rasmussen, L. K., Sorensen, E. S., Petersen, T. E., Nielsen, N. C. et al., Characterization of phosphate sites in native ovine, caprine, and bovine casein micelles and their caseinomacropeptides: a solid state phosphorus-31 nuclear magnetic resonance and sequence and mass spectrometric study. J. Dairy Sci. 1997, 80, 607-614.