2-[(Azidoacetyl)amino]-2-deoxy-D-glucopyranose 1,3,4,6-tetraacetate

1,3,4,6-Tetra-O-acetyl-N-azidoacetylglucosamine is an important organic building block to synthetize substituted glucosamine products.

N-azidoacetylglucosamine-tetraacylated (Ac4GlcNAz) is an azido-tagged analogue of N-acetylglucosamine (GlcNAC). It features azide functionality on the N-acyl side chain and is acetylated to aid in cell membrane permeation. Once in the cell, the acetylated compound is deprotected and takes part in the hexosamine biosynthetic pathway by action of GlcNAc kinase. The resulting modified proteins are detected by the addition of fluorescent tags under Cu(I)-catalyzed azide-alkyne cycloaddition conditions.

N-azidoacetylglucosamine-tetraacylated (Ac4GlcNAz) provides the first part of a simple and robust two-step technique that helps identify and characterize cell surface sialic acid-containing glycoproteins. The acetyl groups increase cell permeability and allow the unnatural sugars to easily pass through the cell membrane. Carboxyesterases remove the acetyl groups once the monosaccharide is in the cell. The azide-modified protein is detected with either fluorescent alkynes or biotin alkyne.

N-Azidoacetylglucosamine is a metabolic glycoprotein labeling reagent that is introduced metabolically in model organisms. The reactive azide group in N-Azidoacetylglucosamine will react with phosphines for visualization or selective capture.