P-GlcNPoc

Product information

• Function

  P-GlcNPoc is an unnatural N-Acetylglucosamine derivative used for the metabolic labeling of GlcNAc residues in cells.¹

• Mode of action

  P-GlcNPoc is passively taken-up by cells and incorporated in glycans. Labeling with P-GlcNPoc showed labeling of a known O-GlcNAcylated protein NEDD4 hence confirming incorporation as a GlcNAc surrogate. Other HexNAc derivatives such as P-ManNPoc and P-GalNPoc were also shown to interconvert to GlcNPoc and label NEDD4.¹ P-ManNPoc does so with comparable efficiency as P-GlcNPoc but is also converted to Neu5NPoc and labels cell surface sialoglycans.² P-GalNPoc labels NEDD4 but does so less efficiently than P-GlcNPoc. P-GlcNPoc contains a Poc group for “click” chemistry using azide reagents. These azides can be modified with an affinity tag or fluorophore for example.

• Applications

  Metabolic labeling of GlcNAc residues in cells for isolation and visualization.

• Handling

  P-GlcNPoc is soluble in DMSO and PBS and is added to cell culture from a stock solution. Incubation of the cells with P-GlcNPoc results in a detectable signal after 4 hrs. Glycans decorated with GlcNPoc residues can be used to perform “click” chemistry. Please see our click chemistry page for suitable reaction partners.

• Chemical Information

  CAS No.: 488744-00-9
  SMILES: O=C(OCC#C)N[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)OC1OC(C)=O
  Chemical formula: C₁₈H₂₃NO₁₁
  Molecular weight: 429.37
  Purity: > 95%
  Identity: ¹H NMR
  Shipping temperature: 20°C
  Storage temperature: 0°C