N-Acetylglucosamine
Biological molecule / From Wikipedia, the free encyclopedia
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N-Acetylglucosamine (GlcNAc) is an amide derivative of the monosaccharide glucose. It is a secondary amide between glucosamine and acetic acid. It is significant in several biological systems.
Names | |
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IUPAC name
β-D-(Acetylamino)-2-deoxy-glucopyranose | |
Other names
N-Acetyl-D-glucosamine GlcNAc NAG | |
Identifiers | |
3D model (JSmol) |
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1247660 | |
ChEBI | |
ChEMBL | |
ChemSpider |
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ECHA InfoCard | 100.028.517 |
EC Number |
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721281 | |
KEGG | |
PubChem CID |
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UNII | |
CompTox Dashboard (EPA) |
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Properties | |
C8H15NO6 | |
Molar mass | 221.21 |
Melting point | 211 |
Related compounds | |
Related Monosaccharides |
N-Acetylgalactosamine |
Related compounds |
Glucosamine Glucose |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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It is part of a biopolymer in the bacterial cell wall, which is 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 exoskeletons of arthropods like insects and crustaceans. It is the main component of the radulas of mollusks, the beaks of cephalopods, and a major component of the cell walls of most fungi.
Polymerized with glucuronic acid, it forms hyaluronan.
GlcNAc has been reported to be an inhibitor of elastase release from human polymorphonuclear leukocytes (range 8–17% inhibition), however this is much weaker than the inhibition seen with N-acetylgalactosamine (range 92–100%).[1]