6-azido-6-deoxy-N-acetyl-glucosamine triacylated (Ac3-6AzGlcNAc)

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6-azido-6-deoxy-N-acetyl-glucosamine triacylated (Ac₃6AzGlcNAc) is an azide-containing, specific metabolic chemical reporter for O-GlcNAcylated proteins. Notably, 6AzGlcNAc cannot be biosynthetically transformed into the corresponding UDP sugar-donor by the canonical salvage-pathway that requires phosphorylation at the 6-hydroxyl. In vitro experiments showed that 6AzGlcNAc can bypass this roadblock through direct phosphorylation of its 1-hydroxyl by the enzyme phosphoacetylglucosamine mutase (AGM1). The azide-modified protein is detected with either fluorescent alkynes or biotin alkyne. 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.

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