P-GlcNTFA

Product information

• Function

  P-GlcNTFA is an unnatural N-acetylglucosamine derivative used for the metabolic labeling of O-GlcNAc residues in cells.¹ The resulting GlcNTFA residues are installed by OGT but cannot be removed by OGA.

• Mode of action

  Proteins carrying single O-GlcNAc residue(s) are found in the cell’s cytoplasm, nucleus and mitochondria. This modification is highly dynamic and O-GlcNAc residues are installed by O-GlcNAc transferase (OGT) and removed by O-GlcNAcase (OGA). P-GlcNTFA is passively taken-up by cells, deactylated and transferred onto proteins by OGT. Depletion of OGT led to a significant reduction in the incorporation of P-GlcNTFA indicating that it is a substrate for OGT. Due to the replacement of the N-acetyl group for a N-trifluoroacetyl (NTFA) group, GlcNTFA residues on proteins are not a substrate for OGA, an enzyme that can remove O-GlcNAc residues. Hence, using this derivative, proteins can be enriched for the GlcNTFA residues as they can be incorporated but not removed. As this disturbs the dynamics of OGT and OGA, the use of this probe is likely to affect the biology as well and effectively acts as an inhibitor of OGA.

• Applications

  Metabolic labeling of O-GlcNAc residues that resist removal by OGA.

• Handling

  P-GlcNTFA is soluble in DMSO and PBS and is added to cell culture from a stock solution. Incubation of the cells with P-GlcNTFA results in a detectable signal after 24 hrs

• Chemical Information

  CAS No.: 7139-63-1
  SMILES: O=C(O[C@H]1[C@H](OC(C)=O)[C@@H](NC(C(F)(F)F)=O)C(OC(C)=O)O[C@@H]1COC(C)=O)C
  Chemical formula: C₁₆H₂₀F₃NO₁₀
  Molecular weight: 443.32
  Purity: > 95%
  Identity: ¹H NMR
  Shipping temperature: 20°C
  Storage temperature: 0°C