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Chemical Compound Review:

SureCN420656 (2S,4S,5R,6R)-5-acetamido-6- [(1R,2R)-3...

Synonyms: CHEBI:21500, HMDB00794, AC1L3XMP, AR-1H5910, Neu5,9Ac2, ...

Schultze, B. et al., Ravindranath, M.H. et al., Höfling, K. et al., Schauer, R. et al., Klotz, F.W. et al., et al.

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Disease relevance of N-Acetyl-9-O-acetylneuraminic acid

The influenza C virus (INF-C) hemagglutinin recognizes 9-O-acetyl-N-acetylneuraminic acid [1].
Inactivation of the cellular receptors by sialate 9-O-acetylesterase and generation of receptors by sialylation of erythrocytes with N-acetyl-9-O-acetylneuraminic acid (Neu5,9Ac2) indicate that S protein recognizes 9-O-acetylated sialic acid as a receptor determinant as has been shown previously for intact virions [2].
Bovine coronavirus uses N-acetyl-9-O-acetylneuraminic acid as a receptor determinant to initiate the infection of cultured cells [3].
Hemagglutinating encephalomyelitis virus attaches to N-acetyl-9-O-acetylneuraminic acid-containing receptors on erythrocytes: comparison with bovine coronavirus and influenza C virus [4].
Identification of 9-O-acetyl-N-acetylneuraminic acid in normal canine pre-ocular tear film secreted mucins and its depletion in Keratoconjunctivitis sicca [5].

High impact information on N-Acetyl-9-O-acetylneuraminic acid

After inactivation, RMG and BSM were found to contain reduced amounts of N-acetyl-9-O-acetylneuraminic acid (Neu5,9Ac2) and increased amounts of N-acetylneuraminic acid (Neu5Ac) [6].
Methyl esterification of the carboxyl group of 9-O-acetyl-N-acetylneuraminic acid significantly reduced the activity of all of the 9-O-Ac-SA esterases against the O-acetyl group [7].
This conclusion was supported by the potent inhibition of hemagglutination by bovine and equine submaxillary mucins which contain 9(7,8)-O-acetyl- and 4-O-acetylsialic acids, respectively, and also by free 9-O-acetyl-N-acetylneuraminic acid (9-O-Ac-NeuAc) and 4-O-Ac-NeuAc relative to NeuAc and NeuGc [8].
Several O-acetylated sialic acids were seen by high-performance liquid chromatography analysis, but N-acetyl-9-O-acetylneuraminic acid prevailed [9].
A synthetic sialic acid, N-acetyl-9-thioacetamidoneuraminic acid (9-ThioAcNeu5Ac), is recognized by influenza C virus as a receptor determinant but-in contrast to the natural receptor determinant, N-acetyl-9-O-acetylneuraminic acid-is resistant to inactivation by the viral acetylesterase [10].

Chemical compound and disease context of N-Acetyl-9-O-acetylneuraminic acid

Influenza C virus spike glycoprotein HEF specifically recognizes glycoconjugates containing 9-O-acetyl-N-acetylneuraminic acid [11].

Biological context of N-Acetyl-9-O-acetylneuraminic acid

The non-natural substrates 4-methyl-umbelliferyl acetate, 4-nitrophenyl acetate, and alpha-naphthyl acetate are cleaved at highest hydrolysis rates, followed by the natural substrate N-acetyl-9-O-acetylneuraminic acid [12].

Anatomical context of N-Acetyl-9-O-acetylneuraminic acid

A simple, one-step synthesis of N-acetyl-9-O-acetylneuraminic acid by enzymic transesterification mediated by porcine pancreas lipase in pyridine [13].
Analysis of the sialic acids obtained by mild acid hydrolysis of B lymphocytes reveals the presence of N-acetylneuraminic acid and 9-O-acetyl-N-acetylneuraminic acid [14].
9-O-Acetyl-N-acetylneuraminic acid was released from bovine submandibular gland mucin, as confirmed by TLC [15].

Associations of N-Acetyl-9-O-acetylneuraminic acid with other chemical compounds

Human erythrocytes contain N-acetylneuraminic acid (Neu5Ac), whereas mouse erythrocytes, which are also invaded by P. falciparum merozoites, contain 9-O-acetyl-N-acetylneuraminic acid (Neu5,9Ac2) and N-glycoloylneuraminic acid (Neu5Gc), in addition to Neu5Ac [16].
Whereas N-acetyl-9-O-acetylneuraminic acid as a component of sialyllactose is nearly as well hydrolyzed as the corresponding free sialic acid, O-acetylated sialoglycoconjugates with high molecular weights (mucins, serum glycoproteins, gangliosides) are not hydrolyzed by this esterase [17].

Gene context of N-Acetyl-9-O-acetylneuraminic acid

Increased influenza A virus sialidase activity with N-acetyl-9-O-acetylneuraminic acid-containing substrates resulting from influenza C virus O-acetylesterase action [18].

Analytical, diagnostic and therapeutic context of N-Acetyl-9-O-acetylneuraminic acid

Synthesis of N-acetyl-9-O-acetylneuraminic acid alpha-p-amino-phenylthioketoside and its application as ligand in the affinity chromatography of a lectin with preferential affinity to O-acetylated sialic acids [19].

References

Selective inactivation of influenza C esterase: a probe for detecting 9-O-acetylated sialic acids. Muchmore, E.A., Varki, A. Science (1987) [Pubmed]
The S protein of bovine coronavirus is a hemagglutinin recognizing 9-O-acetylated sialic acid as a receptor determinant. Schultze, B., Gross, H.J., Brossmer, R., Herrler, G. J. Virol. (1991) [Pubmed]
Bovine coronavirus uses N-acetyl-9-O-acetylneuraminic acid as a receptor determinant to initiate the infection of cultured cells. Schultze, B., Herrler, G. J. Gen. Virol. (1992) [Pubmed]
Hemagglutinating encephalomyelitis virus attaches to N-acetyl-9-O-acetylneuraminic acid-containing receptors on erythrocytes: comparison with bovine coronavirus and influenza C virus. Schultze, B., Gross, H.J., Brossmer, R., Klenk, H.D., Herrler, G. Virus Res. (1990) [Pubmed]
Identification of 9-O-acetyl-N-acetylneuraminic acid in normal canine pre-ocular tear film secreted mucins and its depletion in Keratoconjunctivitis sicca. Corfield, A.P., Donapaty, S.R., Carrington, S.D., Hicks, S.J., Schauer, R., Kohla, G. Glycoconj. J. (2005) [Pubmed]
The receptor-destroying enzyme of influenza C virus is neuraminate-O-acetylesterase. Herrler, G., Rott, R., Klenk, H.D., Müller, H.P., Shukla, A.K., Schauer, R. EMBO J. (1985) [Pubmed]
O-acetylation and de-O-acetylation of sialic acids. Sialic acid esterases of diverse evolutionary origins have serine active sites and essential arginine residues. Hayes, B.K., Varki, A. J. Biol. Chem. (1989) [Pubmed]
Purification and characterization of an O-acetylsialic acid-specific lectin from a marine crab Cancer antennarius. Ravindranath, M.H., Higa, H.H., Cooper, E.L., Paulson, J.C. J. Biol. Chem. (1985) [Pubmed]
Detection of sialic acids and gangliosides with special reference to 9-O-acetylated species in basaliomas and normal human skin. Fahr, C., Schauer, R. J. Invest. Dermatol. (2001) [Pubmed]
Transfer of an esterase-resistant receptor analog to the surface of influenza C virions results in reduced infectivity due to aggregate formation. Höfling, K., Brossmer, R., Klenk, H., Herrler, G. Virology (1996) [Pubmed]
Modification of sialic acids by 9-O-acetylation is detected in human leucocytes using the lectin property of influenza C virus. Zimmer, G., Suguri, T., Reuter, G., Yu, R.K., Schauer, R., Herrler, G. Glycobiology (1994) [Pubmed]
Isolation and characterization of sialate 9(4)-O-acetylesterase from influenza C virus. Schauer, R., Reuter, G., Stoll, S., Posadas del Rio, F., Herrler, G., Klenk, H.D. Biol. Chem. Hoppe-Seyler (1988) [Pubmed]
A simple, one-step synthesis of N-acetyl-9-O-acetylneuraminic acid by enzymic transesterification mediated by porcine pancreas lipase in pyridine. Forstner, M., Freytag, K., Paschke, E. Carbohydr. Res. (1989) [Pubmed]
The nature of sialic acids in human lymphocytes. Kamerling, J.P., Makovitzky, J., Schauer, R., Vliegenthart, J.F., Wember, M. Biochim. Biophys. Acta (1982) [Pubmed]
Properties of sialidase isolated from Actinomyces viscosus DSM 43798. Teufel, M., Roggentin, P., Schauer, R. Biol. Chem. Hoppe-Seyler (1989) [Pubmed]
Binding of Plasmodium falciparum 175-kilodalton erythrocyte binding antigen and invasion of murine erythrocytes requires N-acetylneuraminic acid but not its O-acetylated form. Klotz, F.W., Orlandi, P.A., Reuter, G., Cohen, S.J., Haynes, J.D., Schauer, R., Howard, R.J., Palese, P., Miller, L.H. Mol. Biochem. Parasitol. (1992) [Pubmed]
Partial purification and characterization of sialate O-acetylesterase from bovine brain. Schauer, R., Reuter, G., Stoll, S., Shukla, A.K. J. Biochem. (1989) [Pubmed]
Increased influenza A virus sialidase activity with N-acetyl-9-O-acetylneuraminic acid-containing substrates resulting from influenza C virus O-acetylesterase action. Muñoz-Barroso, I., García-Sastre, A., Villar, E., Manuguerra, J.C., Hannoun, C., Cabezas, J.A. Virus Res. (1992) [Pubmed]
Synthesis of N-acetyl-9-O-acetylneuraminic acid alpha-p-amino-phenylthioketoside and its application as ligand in the affinity chromatography of a lectin with preferential affinity to O-acetylated sialic acids. Reinhard, B., Götz, C., Faillard, H. Biol. Chem. Hoppe-Seyler (1992) [Pubmed]

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