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
Identifiers
131-48-6 YesY
ChEBI CHEBI:61599 YesY
ChemSpider 392681 YesY
Jmol 3D model Interactive image
MeSH N-Acetylneuraminic+Acid
PubChem 439197
  • 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 YesY
    Key: SQVRNKJHWKZAKO-YRMXFSIDSA-N YesY
  • 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 309.273 g/mol
Appearance White crystalline powder
Melting point 186 °C (367 °F; 459 K) (decomposes)
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
Infobox references

N-Acetylneuraminic acid (Neu5Ac or NANA) is the predominant sialic acid found in mammalian cells.

This negatively charged residue is found in complex glycans on mucins and glycoproteins found at the cell membrane. Neu5Ac residues are also found in glycolipids, such 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).

Neu5Ac in the biology of bacterial pathogens

Neu5Ac is also important in the biology of a member of pathogenic bacteria [1][2] as it can used either as a nutrient, providing both carbon and nitrogen to the bacterium, 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 characterised including the NanT protein from Escherichia coli,[3] the SiaPQM TRAP transporter from Haemophilus influenze [4] and the SatABCD ABC transporter from Haemophilus ducreyi.[5]

References

  1. ↑ 1.0 1.1 Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.

See also

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