N-Acetylglucosamine

"GlcNAc" redirects here. Not to be confused with GlyNAC.
N-Acetylglucosamine

Names
IUPAC name
β-D-(Acetylamino)-2-deoxy-glucopyranose
Other names
N-Acetyl-D-glucosamine
GlcNAc
NAG
Identifiers
3D model (JSmol)
1247660
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.028.517 Edit this at Wikidata
EC Number
  • 231-368-2
721281
KEGG
UNII
  • 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 checkY
    Key: OVRNDRQMDRJTHS-FMDGEEDCSA-N checkY
  • InChI=1/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-FMDGEEDCBL
  • O=C(N[C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@H]1O)CO)C
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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N-Acetylglucosamine molecule

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.

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]

  1. ^ Kamel M, Hanafi M, Bassiouni M (1991). "Inhibition of elastase enzyme release from human polymorphonuclear leukocytes by N-acetyl-galactosamine and N-acetyl-glucosamine". Clinical and Experimental Rheumatology. 9 (1): 17–21. PMID 2054963.