P-GalNAz

Product information

• Function

  Metabolic labeling of GlcNAc/GalNAc containing glycans in cells.¹²³⁴

• Mode of action

  P-GalNAz is an unnatural N-acetylgalactosamine derivative used for the metabolic labeling of GlcNAc/GalNAc residues in cells. P-GalNAz is passively taken-up by cells, converted to UDP-GalNAz and partially epimerized to UDP-GlcNAz by UDP-Glucose 4-epimerase (GALE). It was shown that the ratio of UDP-GlcNAz/UDP-GalNAz at equilibrium is 3/1.² In addition, it was shown that P-GalNAz is more efficiently converted into UDP-GlcNAz than P-GlcNAz and hence a more efficient metabolic label of O-GlcNAc residues.² The labeling efficiency and selectivity of P-GalNAz was shown to be dependent on the culture condition. Under high glucose conditions, P-GalNAz treatment resulted in Mucin O-glycan labeling. Under low glucose conditions, P-GalNAz labeled predominantly intracellular O-GlcNAc residues.³ P-GalNAz also leads to UDP-GalNAz which was shown to be preferentially incorporated into mucin O-glycans.¹ Hence, the use of P-GalNAz leads to the labeling of O-GlcNAc and O-GalNAc residues mainly in intracelluar O-GlcNAc and extracellular mucin O-glycans, respectively. P-GalNAz contains an azide group for “click” chemistry using alkyne reagents. These alkynes 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-GalNAz is soluble in DMSO and PBS and is added to cell culture from a stock solution. Glycans decorated with GalNAz residues can be used to perform “click” chemistry. Please see our click chemistry page for suitable reaction partners.

• Chemical Information

  CAS No.: 653600-56-7
  SMILES: O=C(CN=[N+]=[N-])N[C@@H]1[C@@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H](COC(C)=O)OC1OC(C)=O
  Chemical formula: C₁₆H₂₂N₄O₁₀
  Molecular weight: 430.37
  Purity: > 95%
  Identity: ¹H NMR
  Shipping temperature: 20°C
  Storage temperature: -20°C