N-Acetyl-D-glucosamine (CAS: 7512-17-6)

C₈H₁₅NO₆

• N-Acetyl-D-glucosamine (D-GlcNAc) is a non-toxic derivatized glucose monosaccharide found in polymers (Peptidoglycan; PGN) of bacterial cell walls, chitin (e.g. fungi, invertebrates, crustaceans), hyaluronic acids and various glycans. It is also synthesized in the glycosylation pathway as uridine diphosphate (UDP-GlcNAc), which can then be released following degradation of glycosylated proteins.
• Atypical microbial danger signal that acts as a new activator of NLRP3 inflammasome by dissociating the enzyme hexokinase from the mitochondria. D-GlcNAc inhibits purified hexokinase, which is also involved in the glucose metabolism and obesity in mM range. For hexokinase dissociation from the mitochondria much higher concentrations are needed.
• Acceptor substrate for galactosyltransferases. Inhibits the lectin WGA and is used to identify, differentiate and characterize N-acetyl-β-D-hexosaminidase(s).
• Used in the treatment of osteoarthritis and inflammatory bowel disease (IBD), including ulcerative colitis and Crohn's disease. Significantly enhances the prevention of joint damage and inhibits elastase activity and superoxide release from human polymorphonuclear leukocytes. Acts as a cytoprotective agent restoring the integrity and normal function of mucous membrane in humans.
• D-GlcNAc enhances the proliferation and collagen expression of fibroblasts, reduces hyperpigmentation and is therefore considered a valuable ingredient in cosmetics for improving skin wrinkles and color.
• Important substrate for the production of sialic acids.
• Used in multiple other applications in drug development and food supplement, based on a newly described bio-wave model.

1. Inhibition of elastase enzyme release from human polymorphonuclear leukocytes by acetylgalactosamine and N-acetylglucosamine: M. Kamel, et al.;  Clin. Exp. Rheumatol. 9, 17 (1991)
2. N-Periodic phenomena in proteus mirabilis swarm colony development: O. Rauprich, et al.; J. Bacteriol. 178, 6525 (1996)
3. A pilot study of N-acetyl glucosamine, a nutritional substrate for glycosaminoglycan synthesis, in paediatric chronic inflammatory bowel disease: S. Salvatore, et al.; Aliment. Pharmacol. Ther. 14, 1567 (2000)
4. Enhanced healing of cartilaginous injuries by N-Acetyl-D-glucosamine and glucuronic acid: Y. Tamai, et al.; Carbohydr. Polym. 54, 251 (2003)
5. Reduction in the appearance of facial hyperpigmentation by topical N-acetyl glucosamine: D. Bissett, et al.; J. Cosmet. Dermatol. 6, 20 (2007)
6. Production of N-acetyl-neuraminic acid by recombinant whole cells expressing Anabaena sp. CH1 N-acetyl-D-glucosamine 2-epimerase and Escherichia coli N-acetyl-neuraminic acid lyase: Y.C. Lee, et al.; J. Biotechnol. 129, 453 (2007)
7. Effect of different concentrations of collagen, Ceramides, N-acetyl glucosamine, or their mixture on enhancing the proliferation of keratinocytes, fibroblasts and the secretion of collagen and/or the expression of mRNA of type I collagen: R.H. Chen, et al.; J. Food Drug Anal. 16, 66 (2008)
8. N-acetylglucosamine: production and applications: J.K. Chen, et al.; Mar. Drugs. 8, 2493 (2010) (Review)
9. Hexokinase is an innate immune receptor for the detection of bacterial peptidoglycan: A.J. Wolf, et al.; Cell 166, 624 (2016)
10. When Hexokinase Gets that NAG-ing Feeling: D. O'Sullivan, et al.; Cell Metab. 24, 198 (2016)
11. NAGging Hexokinase PEPs up NLRP3: H. Hampton, et al.; Cell Host Microbe 20, 130 (2016)