N-Acetylglucosamine

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Template:Chembox E number
N-Acetylglucosamine
IUPAC name 2-(Acetylamino)-2-deoxy-D-glucose
Other names N-Acetyl-D-Glucosamine
GlcNAc
NAG
Molecular formula C8H15NO6
Identifiers
3D model (JSmol)
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Properties
Molar mass 221.21
Melting point
Hazards
S-phrases S24/25
Related compounds
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

N-Acetylglucosamine (N-Acetyl-D-Glucosamine, or GlcNAc, or NAG) is a monosaccharide derivative of glucose. Chemically it is an amide between glucosamine and acetic acid. It has a molecular formula of C8H15NO6, a molar mass of 221.21 g/mol, and it is significant in several biological systems.

It is part of a biopolymer in the bacterial cell wall, built from alternating units of GlcNAc and N-acetylmuramic acid (MurNAc), cross-linked with oligopeptides at the lactic acid residue of MurNAc. This layered structure is called peptidoglycan.

GlcNAc is the monomeric unit of the polymer chitin, which forms the outer coverings of insects and crustaceans. GlcNAc is also of note in neurotransmission, where it is thought to be an atypical neurotransmitter functioning in nocioceptive (pain) pathways.

It has been proposed as a treatment for autoimmune diseases.[1]

See also

References

  1. "Sugar supplement may treat immune disease - health - 07 June 2007 - New Scientist". Retrieved 2007-06-08.

da:N-acetylglukosamin


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