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N-Acetylneuraminic acid

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N-Acetylneuraminic acid
β anomer
Names
IUPAC name
5-(Acetylamino)-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosonic acid
Other names
  • NANA
  • Neu5Ac
  • Aceneuramic acid
  • Acenobel
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.004.568 Edit this at Wikidata
KEGG
MeSH N-Acetylneuraminic+Acid
UNII
  • InChI=1S/C11H19NO9/c1-4(14)12-7-5(15)2-11(20,10(18)19)21-9(7)8(17)6(16)3-13/h5-9,13,15-17,20H,2-3H2,1H3,(H,12,14)(H,18,19)/t5-,6+,7+,8+,9+,11+/m0/s1 checkY
    Key: SQVRNKJHWKZAKO-YRMXFSIDSA-N checkY
  • InChI=1/C11H19NO9/c1-4(14)12-7-5(15)2-11(20,10(18)19)21-9(7)8(17)6(16)3-13/h5-9,13,15-17,20H,2-3H2,1H3,(H,12,14)(H,18,19)/t5-,6+,7+,8+,9+,11+/m0/s1
    Key: SQVRNKJHWKZAKO-YRMXFSIDBI
  • OC(=O)[C@@]1(O)C[C@H](O)[C@@H](NC(C)=O)[C@@H](O1)[C@H](O)[C@H](O)CO
Properties
C11H19NO9
Molar mass 309.271 g·mol−1
Appearance White crystalline powder
Melting point 186 °C (367 °F; 459 K) (decomposes)
Pharmacology
M09AX05 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

N-Acetylneuraminic acid (Neu5Ac or NANA) is the predominant sialic acid found in human cells, and many mammalian cells. Other forms, such as N-Glycolylneuraminic acid, may also occur in cells.

This residue is negatively charged at physiological pH and is found in complex glycans on mucins and glycoproteins found at the cell membrane. Neu5Ac residues are also found in glycolipids, known as gangliosides, a crucial component of neuronal membranes found in the brain.

Along with involvement in preventing infections (mucus associated with mucous membranes—mouth, nose, GI, respiratory tract), Neu5Ac acts as a receptor for influenza viruses, allowing attachment to mucous cells via hemagglutinin (an early step in acquiring influenzavirus infection).

In the biology of bacterial pathogens

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Neu5Ac is also important in the biology of a number of pathogenic and symbiotic bacteria[1][2][3] as it can be used either as a nutrient, providing both carbon and nitrogen to the bacteria, or in some pathogens, can be activated and placed on the cell surface.[1] Bacteria have evolved transporters for Neu5Ac to enable them to capture it from their environment and a number of these have been characterized including the NanT protein from Escherichia coli,[4] the SiaPQM TRAP transporter from Haemophilus influenzae[5] and the SatABCD ABC transporter from Haemophilus ducreyi.[6]

Medical use

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In Japan, Neu5Ac is approved under the trade name Acenobel for the treatment of distal myopathy with rimmed vacuoles.[7]

See also

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References

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  1. ^ a b Severi E, Hood DW, Thomas GH (2007). "Sialic acid utilization by bacterial pathogens". Microbiology. 153 (9): 2817–2822. doi:10.1099/mic.0.2007/009480-0. PMID 17768226.
  2. ^ Vimr, Eric R.; Kalivoda, Kathryn A.; Deszo, Eric L.; Steenbergen, Susan M. (March 2004). "Diversity of Microbial Sialic Acid Metabolism". Microbiology and Molecular Biology Reviews. 68 (1): 132–153. doi:10.1128/MMBR.68.1.132-153.2004. ISSN 1092-2172. PMC 362108. PMID 15007099.
  3. ^ Vimr ER, Kalivoda KA, Deszo EL, Steenbergen SM (2004). "Diversity of microbial sialic acid metabolism". Microbiol Mol Biol Rev. 68 (1): 132–153. doi:10.1128/mmbr.68.1.132-153.2004. PMC 362108. PMID 15007099.
  4. ^ Vimr ER, Troy FA (1985). "Identification of an inducible catabolic system for sialic acids (nan) in Escherichia coli". J. Bacteriol. 164 (2): 845–853. doi:10.1128/jb.164.2.845-853.1985. PMC 214328. PMID 3902799.
  5. ^ Severi E, Randle G, Kivlin P, Whitfield K, Young R, Moxon R, Kelly D, Hood D, Thomas GH (2005). "Sialic acid transport in Haemophilus influenzae is essential for lipopolysaccharide sialylation and serum resistance and is dependent on a novel tripartite ATP-independent periplasmic transporter". Mol. Microbiol. 58 (4): 1173–1185. doi:10.1111/j.1365-2958.2005.04901.x. PMID 16262798. S2CID 32085592.
  6. ^ Post DM, Mungur R, Gibson BW, Munson RS Jr (2005). "Identification of a novel sialic acid transporter in Haemophilus ducreyi". Infect Immun. 73 (10): 6727–35. doi:10.1128/IAI.73.10.6727-6735.2005. PMC 1230923. PMID 16177350.
  7. ^ ""ACENOBEL® Sustained Release Tablet 500 mg" Approved for Distal Myopathy with Rimmed Vacuoles" (PDF). Nobelpharm.
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