- N-Acetylglucosamine
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N-Acetylglucosamine 
2-(Acetylamino)-2-deoxy-D-glucoseOther namesN-Acetyl-D-Glucosamine
GlcNAc
NAGIdentifiers CAS number 7512-17-6 
PubChem 24139 ChemSpider 22563 UNII V956696549 
ChEBI CHEBI:28009 ChEMBL CHEMBL447878 Jmol-3D images Image 1 - O=C(N[C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@H]1O)CO)C
- 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
Key: OVRNDRQMDRJTHS-FMDGEEDCSA-N
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
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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.
GlcNAc is the monomeric unit of the polymer chitin, which forms the outer coverings of insects and crustaceans.
Polymerized with glucuronic acid, it forms hyaluronan.
Contents
Medical uses
It has been proposed as a treatment for autoimmune diseases[1], and recent tests have claimed some success[2].
See also
- Keratan sulfate
- Chitin
- N-acetyllactosamine synthase
- Wheat germ agglutinin, a plant lectin that binds to this substrate
References
- ^ "Sugar supplement may treat immune disease - health - 07 June 2007 - New Scientist". http://www.newscientist.com/channel/health/mg19426074.500?DCMP=NLC-nletter&nsref=mg19426074.500. Retrieved 2007-06-08.
- ^ http://www.sciencedaily.com/releases/2011/09/110930123057.htm
External links
Pathogenic bacteria Bacterial disease · Coley's Toxins · Exotoxin · Lysogenic cycle
Human flora Substrate preference Oxygen preference Structures Cell wall: Peptidoglycan (NAM, NAG, DAP)
Gram-positive bacteria only: Teichoic acid · Lipoteichoic acid · Endospore
Gram-negative bacteria only: Bacterial outer membrane (Porin, Lipopolysaccharide) · Periplasmic space
Mycobacteria only: Arabinogalactan · Mycolic acidOutside envelopeCompositeShapes Categories:- Glucosamines
- Acetamides
- Membrane biology
- Biochemistry stubs
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