P-GalNPoc

Product information

• Function

  P-GalNPoc is an unnatural N-Acetylgalactosamine derivative used for the metabolic labeling of GlcNAc/GalNAc residues in cells.¹

• Mode of action

  P-GalNPoc is passively taken-up by cells and converted into UDP-GalPoc and epimerized to UDP-GlcNPoc by GALE inside cells and incorporated in glycans. Labeling with P-GalNPoc showed labeling of a known intracellular O-GlcNAcylated protein NEDD4 hence confirming incorporation as a GlcNAc surrogate. Labeling with P-GalNPoc was shown to be less efficient for NEDD4 labeling compared to other HexNAc derivatives such as P-ManNPoc and P-GlcNPoc.¹ Cell surface labeling of P-GalNPoc was also much weaker compared to P-ManNPoc and P-GlcNPoc, consistent with the lower labeling observed for P-GalNAlk.¹ However, in contrast to P-GalNAlk, P-GalNPoc is a substrate for GALE and epimerized to UDP-GlcNPoc. P-GalNPoc contains a Poc group for “click” chemistry with azide reagents. These azides can be modified with an affinity tag or fluorophore for example.

• Applications

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

• Handling

  P-GalNPoc is soluble in DMSO and PBS and is added to cell culture from a stock solution. Incubation of the cells with P-GalNPoc 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.: 1431120-34-1
  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