N-Acetylglucosamine

N-Acetylglucosamine
IUPAC name 2-(Acetylamino)-2-deoxy-D-glucose
Other names N-Acetyl-D-Glucosamine GlcNAc NAG
Identifiers
CAS number	7512-17-6 Y
PubChem	24139
ChemSpider	22563 Y
UNII	V956696549 N
ChEBI	CHEBI:28009 N
ChEMBL	CHEMBL447878 Y
Jmol-3D images	Image 1
SMILES O=C(N[C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@H]1O)CO)C
InChI InChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6-,7-,8-/m1/s1 Y Key: OVRNDRQMDRJTHS-FMDGEEDCSA-N Y
Properties
Molecular formula	C8H15NO6
Molar mass	221.21
Melting point	211
Hazards
S-phrases	S24/25
Related compounds
Related Monosaccharides	N-Acetylgalactosamine
Related compounds	Glucosamine Glucose
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

N-Acetylglucosamine (N-acetyl-D-glucosamine, or GlcNAc, or NAG) is a monosaccharide derivative of glucose. 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 (formerly called murein).

GlcNAc is the monomeric unit of the polymer chitin, which forms the outer coverings of insects and crustaceans. It is the main component of the cell walls of fungi, the radulas of mollusks, and the beaks of cephalopods.

Polymerized with glucuronic acid, it forms hyaluronan.

Medical uses

It has been proposed as a treatment for autoimmune diseases, and recent tests have claimed some success.

See also

• Keratan sulfate
• Chitin
• N-acetyllactosamine synthase
• Wheat germ agglutinin, a plant lectin that binds to this substrate

External links

• Re Multiple Sclerosis