N-Acetylglucosamine

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N-Acetylglucosamine

IUPAC name	2-(Acetylamino)-2-deoxy-D-glucose
Other names	N-Acetyl-D-Glucosamine GlcNAc NAG
Molecular formula	C₈H₁₅NO₆
Identifiers
CAS number	[7512-17-6]
PubChem	24139
SMILES	[H][C@](C([H])(CO)O[C@@](O) ([H])[C@@](NC(C)=O)1[H])(O)[C@@]1(O)[H]
Properties
Molar mass	221.21
Melting point	211
Hazards
S-phrases	S24/25
Related compounds
Related Monosaccharides	N-Acetylgalactosamine
Related compounds	Glucosamine Glucose
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 C₈H₁₅N O₆, 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]