Specific metabolic label of intracellular β-O-GlcNAc residues
|Tags:||Azide, Bioorthogonal chemistry, Metabolic label, N-Acetyl-Galactosamine, N-Acetyl-Glucosamine, OGA, OGT|
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Selective metabolic labeling of intracellular β-O-GlcNAc containing glycans in cells.1
Mode of action
P-GalNAc6Az is an unnatural N-acetylgalactosamine derivative used for the metabolic labeling of intracellular β-O-GlcNAc residues in cells. Proteins carrying single β-O-GlcNAc residue(s) are found in the cell’s cytoplasm, nucleus and mitochondria. This modification is highly dynamic. P-GalNAc6Az specifically labels these intracellular O-GlcNAc residues and not luminal of extracellular glycoproteins. P-GalNAc6Az is passively taken up in cells and converted into UDP-GalNAc6Az. UDP-GalNAc6Az is not incorporated into cellular glycans to an appreciable extend.2 Instead, it is epimerized to UDP-GlcNAc6Az by GALE. UDP-GlcNAc6Az was shown to be a substrate for OGT and was only incorporated into intracellular proteins and not luminal or extracellular proteins.2 P-GalNAc6Az is converted via the galactosamine salvage pathway whereas P-GlcNAc6Az is converted by the glucosamine salvage pathway. Both lead to the intracellular formation of UDP-GlcNAc6Az and selective labeling of intracellular O-GlcNAc. Hence, P-GalNAc6Az is a highly specific label of intracellular proteins unlike P-GlcNAz and P-GalNAz which also label extracellular GlcNAc and GalNAc residues.2 GlcNAc6Az residues on proteins were still a substrate for OGA, an enzyme that can remove these residues. For a selective intracellular β-O-GlcNAc labeling reagent that is transferred by OGT but resistant to action of OGA we refer to P-Glc6Az. P-GalNAc6Az contains an azide group for “click” chemistry. The azide can be reacted with an alkyne reagent on fixed cells. These alkynes can be modified with an affinity tag or fluorophore for example. Please see our click chemistry page for suitable reaction partners.
Selective metabolic labeling of intracellular β-O-GlcNAc residues in cells for isolation and visualization.
P-GalNAc6Az is soluble in DMSO and PBS and is added to cell culture from a stock solution. Glycans decorated with GlcNAc6Az residues can be used to perform “click” chemistry. Please see our click chemistry page for suitable reaction partners.
CAS No.: NA
Chemical formula: C14H20N4O8
Molecular weight: 372.33
Purity: > 95%
Identity: 1H NMR
Shipping temperature: 20°C
Storage temperature: 0°C
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