P-GlcNAc6Az

Product information

• Function

  Selective metabolic labeling of intracellular β-O-GlcNAc containing glycans in cells.¹

• Mode of action

  P-GlcNAc6Az is an unnatural N-acetylglucosamine derivative used for the selective 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-GlcNAc6Az specifically labels these intracellular O-GlcNAc residues and not luminal of extracellular glycoproteins. P-GlcNAc6Az is passively taken up in cells and converted into UDP-GlcNAc6Az. Due to the presence of the 6-azido group, phosphorylation at the 6-position is not possible. It was shown that GlcNAc6Az can be phosphorylated at the 1-position by AGM1 followed by conversion into UDP-GlcNAc6Az by AGX1.¹ UDP-GlcNAc6Az was shown to be a substrate for OGT and was only incorporated into intracellular proteins and not luminal or extracellular proteins. Hence, P-GlcNAc6Az is a highly specific label of intracellular proteins unlike P-GlcNAz and P-GalNAz which also label extracellular GlcNAc and GalNAc residues.¹ 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-GlcNAc6Az 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.

• Applications

  Selective metabolic labeling of intracellular β-O-GlcNAc residues in cells for isolation and visualization.

• Handling

  P-GlcNAc6Az 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.

• Chemical Information

  CAS No.: NA
  SMILES: O=C(O[C@H]1[C@H](OC(C)=O)[C@@H](NC(C)=O)C(OC(C)=O)O[C@@H]1CN=[N+]=[N-])C
  Chemical formula: C₁₄H₂₀N₄O₈
  Molecular weight: 372.33
  Purity: > 95%
  Identity: ¹H NMR
  Shipping temperature: 20°C
  Storage temperature: 0°C