P-GlcNAlk

Product information

• Function

  Selective metabolic labeling of GlcNAc containing glycans in cells.

• Mode of action

  P-GlcNAlk is an unnatural N-acetylglucosamine derivative used for the metabolic labeling of GlcNAc residues in cells.¹ P-GlcNAlk is passively taken-up by cells, converted to UDP-GlcNAlk and incorporated in glycans. Labeling with P-GlcNAlk demonstrated that depending on the conditions, N-glycans and intracellular O-GlcNAc residues were labeled. Under high glucose conditions, P-GlcNAlk treatment resulted in N-glycans labeling (labeling signal was sensitive for PNGase-F treatment). Under low glucose conditions, P-GlcNAlk labeled mostly intracellular O-GlcNAc residues.¹ Furthermore, it was shown that UDP-GlcNAlk is not epimerized to UDP-GalNAlk and vica versa and hence represents a very specific label of GlcNAc residues. Compared to other probes that can be used to label GlcNAc residues (P-GlcNPoc, P-GlcNAz, P-GalNAz) P-GlcNAlk is a more specific probe as it is not readily interconverted to other monosaccharides. Due to its specificity, P-GlcNAlk was used to identify new glycoproteins using metabolic labeling. The glycosylation of NEDD4-1 was discovered using P-GlcNAlk. P-GlcNAlk contains an alkyne 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-GlcNAlk is soluble in DMSO and PBS and is added to cell culture from a stock solution. Glycans decorated with GlcNAlk 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(CCC#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: C₁₉H₂₅NO₁₀
  Molecular weight: 427.40
  Purity: > 95%
  Identity: ¹H NMR
  Shipping temperature: 20°C
  Storage temperature: 0°C