Abstract
O-Acetylation is one of the major modifications of sialic acids that significantly alters biological properties of the parent molecule. These O-acetylated forms are components of the cellular membrane and can affect physiological and pathological responses. Understanding the role of N-glycans in physiology is of increasing relevance to cellular biologists in various disciplines who study glycoproteomics yet lack information regarding the function of the attached glycans. However, permethylation, the most common mass spectrometric analytical means, leads to the loss of O-linked acetyl groups in sialic acids. In this chapter, we demonstrated that O-acetylation of sialic acid in Atlantic salmon serum N-glycan can be well investigated by capillary electrophoresis–mass spectrometry.
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References
Turnbull, J. E. and Field, R. A., (2007) Emerging glycomics technologies. Nat. Chem. Biol. 3, 74–77.
Klein, A. and Roussel, P., (1998) O-acetylation of sialic acids. Biochimie 80, 49–57.
Schauer, R. (2000) Achievements and challenges of sialic acid research. Glycoconj. J. 17, 485–499.
Varki, A. (1992) Diversity in the sialic acids. Glycobiology 3, 25–40.
Campbell, F., Appleton, M. A., Fuller, C. E., Greeff, M. P., Hallgrimsson, J., Katoh, R., Ng, O. L., Satir, A., Williams, G. T., and Williams, E. D. (1994) Racial variation in the O-acetylation phenotype of human colonic mucosa. J. Pathol. 174, 169–174.
Corfield, A. P., Wagner, S. A., Paraskeva, C., Clamp, J. R., Durdey, P., Reuter, G., and Schauer, R., (1992) Loss of sialic acid O-acetylation in human colorectal cancer cells. Biochem. Soc. Trans. 20, 94S.
Corfield, A. P., Myerscough, N., Warren, B. F., Durdey, P., Paraskeva, C., and Schauer, R. (1999) Reduction of sialic acid O-acetylation in human colonic mucins in the adenoma-carcinoma sequence. Glycoconj. J. 16, 307–317.
Ghosh, S., Bandyopadhyay, S., Mallick, A., Pal, S., Vlasak, R., Bhattacharya, D. K., and Mandal, C. (2005) Interferon gamma promotes survival of lymphoblasts overexpressing 9-O-acetylated sialoglycoconjugates in childhood acute lymphoblastic leukaemia (ALL). J. Cell Biochem. 95, 206–216.
Ghosh, S., Bandyopadhyay, S., Mukherjee, K., Mallick, A., Pal, S., Mandal, C., Bhattacharya, D. K., and Mandal, C. (2007) O-acetylation of sialic acids is required for the survival of lymphoblasts in childhood acute lymphoblastic leukemia (ALL). Glycoconj. J. 24, 17–24.
Shen, Y., Tiralongo, J., Iwersen, M., Sipos, B., Kalthoff, H., and Schauer, R. (2002) Characterization of the sialate-7(9)-O-acetyltransferase from the microsomes of human colonic mucosa. Biol. Chem. 383, 307–317.
Shen, Y., Tiralongo, J., Kohla, G., and Schauer, R. (2004) Regulation of sialic acid O-acetylation in human colon mucosa. Biol. Chem. 385, 145–152.
Shen, Y., Kohla, G., Lrhorfi, A. L., Sipos, B., Kalthoff, H., Gerwig, G. J., Kamerling, J. P., Schauer, R., and Tiralongo, J., (2004) O-acetylation and de-O-acetylation of sialic acids in human colorectal carcinoma. Eur. J. Biochem. 271, 281–290.
Shi, W. X., Chammas, R., and Varki, A. (1996) Regulation of sialic acid 9-O-acetylation during the growth and differentiation of murine erythroleukemia cells. J. Biol. Chem. 271, 31517–31525.
Sjoberg, E. R., Powell, L. D., Klein, A., and Varki, A. (1994) Natural ligands of the B cell adhesion molecule CD22 beta can be masked by 9-O-acetylation of sialic acids. J. Cell Biol. 126, 549–562.
Butor, C., Diaz, S., and Varki, A. (1993) High level O-acetylation of sialic acids on N-linked oligosaccharides of rat liver membranes. Differential subcellular distribution of 7- and 9-O-acetyl groups and of enzymes involved in their regulation. J. Biol. Chem. 268, 10197–10206.
Morimoto, N., Nakano, M., Kinoshita, M., Kawabata, A., Morita, M., Oda, Y., Kuroda, R., and Kakehi, K., (2001) Specific distribution of sialic acids in animal tissues as examined by LC-ESI-MS after derivatization with 1,2-diamino-4,5-methylenedioxybenzene. Anal. Chem. 73, 5422–5428.
Stehling, P., Gohlke, M., Fitzner, R., and Reutter, W. (1998) Rapid analysis of O-acetylated neuraminic acids by matrix assisted laser desorption/ionization time-of-flight mass spectrometry. Glycoconj. J. 15, 339–344.
Hara, S., Yamaguchi, M., Takemori, Y., Furuhata, K., Ogura, H., and Nakamura, M. (1989) Determination of mono-O-acetylated N-acetylneuraminic acids in human and rat sera by fluorometric high-performance liquid chromatography. Anal. Biochem. 179, 162–166.
Higa, H. H., Manzi, A. and Varki, A., (1989) O-acetylation and de-O-acetylation of sialic acids. Purification, characterization, and properties of a glycosylated rat liver esterase specific for 9-O-acetylated sialic acids. J. Biol. Chem. 264, 19435–19442.
Harvey, D. J., (2006) Analysis of carbohydrates and glycoconjugates by matrix-assisted laser desorption/ionization mass spectrometry: An update covering the period 1999-2000. Mass Spectrom. Rev. 25, 595–662.
Liu, X., Li, X., Chan, K., Zou, W., Pribil, P., Li, X. F., Sawyer, M. B., and Li, J. (2007) “One-pot" methylation in glycomics application: esterification of sialic acids and permanent charge construction. Anal. Chem. 79, 3894–3900.
Sekiya, S., Wada, Y. and Tanaka, K., (2005) Derivatization for stabilizing sialic acids in MALDI-MS. Anal. Chem. 77, 4962–4968.
Sagi, D., Kienz, P., Denecke, J., Marquardt, T., and Peter-Katalinic, J. (2005) Glycoproteomics of N-glycosylation by in-gel deglycosylation and matrix-assisted laser desorption/ionisation-time of flight mass spectrometry mapping: application to congenital disorders of glycosylation. Proteomics. 5, 2689–2701.
Ylonen, A., Kalkkinen, N., Saarinen, J., Bogwald, J., and Helin, J. (2001) Glycosylation analysis of two cysteine proteinase inhibitors from Atlantic salmon skin: di-O-acetylated sialic acids are the major sialic acid species on N-glycans. Glycobiology 11, 523–531.
Ylonen, A., Helin, J., Bogwald, J., Jaakola, A., Rinne, A., and Kalkkinen, N., (2002) Purification and characterization of novel kininogens from spotted wolffish and Atlantic cod. Eur. J. Biochem. 269, 2639–2646.
Liu, X., Afonso, L., Altman, E., Johnson, S., Brown, L., and Li, J. (2008) O-acetylation of sialic acids in N-glycans of Atlantic salmon (Salmo salar) serum is altered by handling stress. Proteomics 8, 2849–2857.
Kang, P., Mechref, Y., Kyselova, Z., Goetz, J. A., and Novotny, M. V. (2007) Comparative glycomic mapping through quantitative permethylation and stable-isotope labeling. Anal. Chem. 79, 6064–6073.
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Liu, X., Afonso, L. (2010). Is Permethylation Strategy Always Applicable to Protein N-Glycosylation Study?: A Case Study on the O-Acetylation of Sialic Acid in Fish Serum Glycans. In: Li, J. (eds) Functional Glycomics. Methods in Molecular Biology, vol 600. Humana Press. https://doi.org/10.1007/978-1-60761-454-8_18
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DOI: https://doi.org/10.1007/978-1-60761-454-8_18
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