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Chemical Compound Review

sialic acid     (2R,4S,5R,6R)-5-acetamido- 2,4-dihydroxy-6...

Synonyms: alpha-Neu5Ac, O-sialic acid, SureCN79085, CHEMBL1234621, CHEBI:49026, ...
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Disease relevance of sialic acid


Psychiatry related information on sialic acid

  • Salla disease is a lysosomal storage disorder characterized by mental retardation and disturbed sialic acid metabolism [6].
  • In senile dementia, marked diminution of total ganglioside sialic acid per neuron and galactocerebroside per cell in the lower lamina far exceeded alterations associated with aging itself [7].
  • Neuraminidase treatment of proteoglycan-deficient cells restores permissiveness to GDVII virus, indicating that sialic acid hinders direct access of virus to the protein entry receptor [8].
  • The forms of transferrin deficient in sialic acid and/or carbohydrate, termed carbohydrate-deficient transferrin (CDT), have been of clinical interest for almost two decades as a result of the initial finding that elevated CDT concentrations are associated with chronic, excessive alcohol abuse [9].
  • Carbohydrate-deficient transferrin (CDT) is the most specific marker for diagnosis of chronic excessive alcohol consumption and includes the serum transferrin (Tf) isoforms with two or less sialic acid residues (di-, mono-, and asialo-Tf) [10].

High impact information on sialic acid

  • CD22 is a member of the Ig superfamily that serves as an adhesion receptor for sialic acid-bearing ligands expressed on erythrocytes and all leukocyte classes [11].
  • ST3Gal-I induction and attendant core 1 sialic acid addition to CD8beta on mature thymocytes decreases CD8alphabeta-MHCI avidity by altering CD8alphabeta domain-domain association and/or orientation [12].
  • Our observations suggest that mutations in SLC17A5 are the primary cause of lysosomal sialic acid storage diseases [1].
  • Progressive cerebellar atrophy and dysmyelination have been documented by magnetic resonance imaging (ref. 4). Enlarged lysosomes are seen on electron microscopic studies and patients excrete large amounts of free sialic acid in urine [1].
  • Sialidase (neuraminidase, EC catalyses the hydrolysis of terminal sialic acid residues of glyconjugates [13].

Chemical compound and disease context of sialic acid


Biological context of sialic acid


Anatomical context of sialic acid

  • A H+/anionic sugar symporter mechanism for sialic acid and glucuronic acid is impaired in lysosomal membranes from Salla and ISSD patients [1].
  • A second type of receptor, largely masked by sialic acid, appears throughout the extracellular matrix [23].
  • However, sialic acid-containing receptors have been implicated in the adherence of M. pneumoniae to erythrocytes and other cell types, and both I and the related antigen i occur on erythrocytes in sialylated form: i is the predominant antigen on fetal erythrocytes and I is predominant in adults [24].
  • Sialic acid residues are important calcium-binding sites in the matrix and treatment with neuraminidase, an enzyme which cleaves sialic acid from oligosaccharide chains, has been reported to abolish spontaneous contraction in cultured heart cells, without causing general breakdown in the plasma membrane [25].
  • MAdCAM-1 isolated from mesenteric lymph nodes, but not from cultured endothelioma cells, bears N-glycanase-resistant sialic acid-containing carbohydrate which supports adhesion of L-selectin-transfected lymphoid cells under shear [26].

Associations of sialic acid with other chemical compounds


Gene context of sialic acid


Analytical, diagnostic and therapeutic context of sialic acid


  1. A new gene, encoding an anion transporter, is mutated in sialic acid storage diseases. Verheijen, F.W., Verbeek, E., Aula, N., Beerens, C.E., Havelaar, A.C., Joosse, M., Peltonen, L., Aula, P., Galjaard, H., van der Spek, P.J., Mancini, G.M. Nat. Genet. (1999) [Pubmed]
  2. Efficacy and safety of the neuraminidase inhibitor zanamivir in the treatment of influenzavirus infections. GG167 Influenza Study Group. Hayden, F.G., Osterhaus, A.D., Treanor, J.J., Fleming, D.M., Aoki, F.Y., Nicholson, K.G., Bohnen, A.M., Hirst, H.M., Keene, O., Wightman, K. N. Engl. J. Med. (1997) [Pubmed]
  3. Structure of the influenza virus haemagglutinin complexed with its receptor, sialic acid. Weis, W., Brown, J.H., Cusack, S., Paulson, J.C., Skehel, J.J., Wiley, D.C. Nature (1988) [Pubmed]
  4. O-acetylation of disialoganglioside GD3 by human melanoma cells creates a unique antigenic determinant. Cheresh, D.A., Reisfeld, R.A., Varki, A.P. Science (1984) [Pubmed]
  5. Metastatic potential is positively correlated with cell surface sialylation of cultured murine tumor cell lines. Yogeeswaran, G., Salk, P.L. Science (1981) [Pubmed]
  6. Studies on the defect underlying the lysosomal storage of sialic acid in Salla disease. Lysosomal accumulation of sialic acid formed from N-acetyl-mannosamine or derived from low density lipoprotein in cultured mutant fibroblasts. Renlund, M., Kovanen, P.T., Raivio, K.O., Aula, P., Gahmberg, C.G., Ehnholm, C. J. Clin. Invest. (1986) [Pubmed]
  7. Aging, senile dementia, and the intralaminar microchemistry of cerebral cortex. DeKosky, S.T., Bass, N.H. Neurology (1982) [Pubmed]
  8. Heparan sulfate mediates infection of high-neurovirulence Theiler's viruses. Reddi, H.V., Lipton, H.L. J. Virol. (2002) [Pubmed]
  9. Direct capillary electrophoretic detection of carbohydrate-deficient transferrin in neat serum. Trout, A.L., Prasad, R., Coffin, D., DiMartini, A., Lane, T., Blessum, C., Khatter, N., Landers, J.P. Electrophoresis (2000) [Pubmed]
  10. Capillary zone electrophoresis for determination of carbohydrate-deficient transferrin in human serum. Fermo, I., Germagnoli, L., Soldarini, A., Dorigatti, F., Paroni, R. Electrophoresis (2004) [Pubmed]
  11. CD22, a B lymphocyte-specific adhesion molecule that regulates antigen receptor signaling. Tedder, T.F., Tuscano, J., Sato, S., Kehrl, J.H. Annu. Rev. Immunol. (1997) [Pubmed]
  12. Developmentally regulated glycosylation of the CD8alphabeta coreceptor stalk modulates ligand binding. Moody, A.M., Chui, D., Reche, P.A., Priatel, J.J., Marth, J.D., Reinherz, E.L. Cell (2001) [Pubmed]
  13. Cloning, expression and chromosomal mapping of human lysosomal sialidase and characterization of mutations in sialidosis. Pshezhetsky, A.V., Richard, C., Michaud, L., Igdoura, S., Wang, S., Elsliger, M.A., Qu, J., Leclerc, D., Gravel, R., Dallaire, L., Potier, M. Nat. Genet. (1997) [Pubmed]
  14. Defective sialic acid egress from isolated fibroblast lysosomes of patients with Salla disease. Renlund, M., Tietze, F., Gahl, W.A. Science (1986) [Pubmed]
  15. Direct colorimetric detection of a receptor-ligand interaction by a polymerized bilayer assembly. Charych, D.H., Nagy, J.O., Spevak, W., Bednarski, M.D. Science (1993) [Pubmed]
  16. Serum protein-bound carbohydrates for following the course of disease in patients with metastatic breast carcinoma. Waalkes, T.P., Mrochek, J.E., Dinsmore, S.R., Tormey, D.C. J. Natl. Cancer Inst. (1978) [Pubmed]
  17. Isolation and characterization of a novel vitamin B12-binding protein associated with hepatocellular carcinoma. Burger, R.L., Waxman, S., Gilbert, H.S., Mehlman, C.S., Allen, R.H. J. Clin. Invest. (1975) [Pubmed]
  18. Chloroquine and ammonium chloride prevent terminal glycosylation of immunoglobulins in plasma cells without affecting secretion. Thorens, B., Vassalli, P. Nature (1986) [Pubmed]
  19. Complement targeting of nonhuman sialic acid does not mediate cell death of human embryonic stem cells. Mart??n, M.J., Muotri, A., Gage, F.H., Varki, A. Nat. Med. (2006) [Pubmed]
  20. Predicting the evolution of human influenza A. Bush, R.M., Bender, C.A., Subbarao, K., Cox, N.J., Fitch, W.M. Science (1999) [Pubmed]
  21. UDP-GlcNAc 2-epimerase: a regulator of cell surface sialylation. Keppler, O.T., Hinderlich, S., Langner, J., Schwartz-Albiez, R., Reutter, W., Pawlita, M. Science (1999) [Pubmed]
  22. Hepatic binding protein: the protective role of its sialic acid residues. Stockert, R.J., Morell, A.G., Scheinberg, I.H. Science (1977) [Pubmed]
  23. Peanut lectin receptors in the early amphibian embryo: regional markers for the study of embryonic induction. Slack, J.M. Cell (1985) [Pubmed]
  24. Erythrocyte receptors for Mycoplasma pneumoniae are sialylated oligosaccharides of Ii antigen type. Loomes, L.M., Uemura, K., Childs, R.A., Paulson, J.C., Rogers, G.N., Scudder, P.R., Michalski, J.C., Hounsell, E.F., Taylor-Robinson, D., Feizi, T. Nature (1984) [Pubmed]
  25. Removal of sialic acid from cardiac sarcolemma does not affect contractile function in electrically stimulated guinea pig left atria. Harding, S.E., Halliday, J. Nature (1980) [Pubmed]
  26. L-selectin-mediated lymphocyte rolling on MAdCAM-1. Berg, E.L., McEvoy, L.M., Berlin, C., Bargatze, R.F., Butcher, E.C. Nature (1993) [Pubmed]
  27. Demonstration of an extensive trans-tubular network continuous with the Golgi apparatus stack that may function in glycosylation. Roth, J., Taatjes, D.J., Lucocq, J.M., Weinstein, J., Paulson, J.C. Cell (1985) [Pubmed]
  28. Sulfation and phosphorylation of the neural cell adhesion molecule, N-CAM. Sorkin, B.C., Hoffman, S., Edelman, G.M., Cunningham, B.A. Science (1984) [Pubmed]
  29. Bovine gamma/delta T cells bind E-selectin via a novel glycoprotein receptor: first characterization of a lymphocyte/E-selectin interaction in an animal model. Walcheck, B., Watts, G., Jutila, M.A. J. Exp. Med. (1993) [Pubmed]
  30. Rosette formation between human lymphocytes and sheep erythrocytes. Inhibition of rosette formation by specific glycopeptides. Boldt, D.H., Armstrong, J.P. J. Clin. Invest. (1976) [Pubmed]
  31. Isolation, purification, and characterization of a mouse plasmacytoma cell surface glycoprotein involved in the resistance of the tumor cells to immune destruction. Rosenstein, Y., Theelen, M., Sánchez, I., Celis, E. J. Natl. Cancer Inst. (1985) [Pubmed]
  32. Enhanced inhibition of hepatitis B virus production by asialoglycoprotein receptor-directed interferon. Eto, T., Takahashi, H. Nat. Med. (1999) [Pubmed]
  33. Identification and molecular cloning of p75/AIRM1, a novel member of the sialoadhesin family that functions as an inhibitory receptor in human natural killer cells. Falco, M., Biassoni, R., Bottino, C., Vitale, M., Sivori, S., Augugliaro, R., Moretta, L., Moretta, A. J. Exp. Med. (1999) [Pubmed]
  34. The selectin GMP-140 binds to sialylated, fucosylated lactosaminoglycans on both myeloid and nonmyeloid cells. Zhou, Q., Moore, K.L., Smith, D.F., Varki, A., McEver, R.P., Cummings, R.D. J. Cell Biol. (1991) [Pubmed]
  35. Embryonic to adult conversion of neural cell adhesion molecules in normal and staggerer mice. Edelman, G.M., Chuong, C.M. Proc. Natl. Acad. Sci. U.S.A. (1982) [Pubmed]
  36. Integrated regulatory responses of fimB to N-acetylneuraminic (sialic) acid and GlcNAc in Escherichia coli K-12. Sohanpal, B.K., El-Labany, S., Lahooti, M., Plumbridge, J.A., Blomfield, I.C. Proc. Natl. Acad. Sci. U.S.A. (2004) [Pubmed]
  37. Muscle proteolysis induced by a circulating peptide in patients with sepsis or trauma. Clowes, G.H., George, B.C., Villee, C.A., Saravis, C.A. N. Engl. J. Med. (1983) [Pubmed]
  38. A novel sialic acid binding site on factor H mediates serum resistance of sialylated Neisseria gonorrhoeae. Ram, S., Sharma, A.K., Simpson, S.D., Gulati, S., McQuillen, D.P., Pangburn, M.K., Rice, P.A. J. Exp. Med. (1998) [Pubmed]
  39. Identification of the C5a des Arg cochemotaxin. Homology with vitamin D-binding protein (group-specific component globulin). Perez, H.D., Kelly, E., Chenoweth, D., Elfman, F. J. Clin. Invest. (1988) [Pubmed]
  40. Qualitative and quantitative changes in sialomucins during 1,2-dimethylhydrazine-induced colon carcinogenesis in the rat. McGarrity, T.J., Via, E.A., Colony, P.C. J. Natl. Cancer Inst. (1987) [Pubmed]
  41. Identification of a major sialoprotein in the glycocalyx of human visceral glomerular epithelial cells. Kerjaschki, D., Poczewski, H., Dekan, G., Horvat, R., Balzar, E., Kraft, N., Atkins, R.C. J. Clin. Invest. (1986) [Pubmed]
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