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N-Acetylneuraminic acid

| NANA | Neu5Ac | Aceneuramic acid | Acenobel}}

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

Neu5Ac is also important in the biology of a number of pathogenic and symbiotic bacteria 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. the SiaPQM TRAP transporter from Haemophilus influenzae and the SatABCD ABC transporter from Haemophilus ducreyi.

Medical use

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

References

References

  1. (2007). "Sialic acid utilization by bacterial pathogens". Microbiology.
  2. (2004). "Diversity of microbial sialic acid metabolism.". Microbiol Mol Biol Rev.
  3. (1985). "Identification of an inducible catabolic system for sialic acids (nan) in Escherichia coli". J. Bacteriol..
  4. (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..
  5. (2005). "Identification of a novel sialic acid transporter in Haemophilus ducreyi.". Infect Immun.
  6. "“ACENOBEL® Sustained Release Tablet 500 mg” Approved for Distal Myopathy with Rimmed Vacuoles". Nobelpharm.
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amino-sugars sugar-acids monosaccharides
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