N-Acetylglucosamine
IUPAC name	2-(Acetylamino)-2-deoxy-D-glucose
Other names	N-Acetyl-D-Glucosamine GlcNAc NAG
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]
ChemSpider ID	22563
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
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. GlcNAc is also of note in neurotransmission, where it is thought to be an atypical neurotransmitter functioning in nocioceptive (pain) pathways.

Polymerized with glucuronic acid it forms hyaluronan.

Contents 1 Medical uses 2 See also 3 References 4 External links

[edit] Medical uses

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

[edit] See also

• Keratan sulfate
• Chitin
• N-acetyllactosamine synthase

[edit] References

1. ^ "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. 

[edit] External links

• N-AcetylGlucosamine
• Re Multiple Sclerosis

v • d • e Microbiology: Bacteria Pathogenic bacteria Bacterial disease · Coley's Toxins · Exotoxin · Lysogenic cycle Human flora Gut flora · Skin flora · Vaginal flora Substrate preference Lipophilic · Saccharophilic Oxygen preference Aerobic (Obligate) · Anaerobic (Facultative, Obligate) · Microaerophile · Nanaerobe · Aerotolerant Structures Cell envelope Cell membrane 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 acid Outside envelope Bacterial capsule · Slime layer · S-layer · Glycocalyx Pilus · Fimbria Composite Biofilm Shapes Bacterial cellular morphologies · Coccus (Diplococcus)  · Bacillus · Coccobacillus

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