P-GlcNAc

Product information

• Function

  P-GlcNAc is a control compound for labeling/inhibition experiments utilizing acetylated glucosamine derivatives P-GlcNAc4D, P-GlcNAc6Ac, P-GlcNAz, P-GlcNPoc, P-GlcNTFA

• Mode of action

  P-GlcNAc is taken up by cells via passive diffusion because this compound contains O-acetyl (OAc) groups. These groups make the molecule more lipophilic so that it can passively diffuse over mammalian cell membranes. Inside cells, these O-acetyl groups are removed via non-specific esterase releasing N-acetylglucosamine and acetic acid. It is possible that at high concentrations, the released acetic acid or the partially acetylated intermediates are toxic. In addition, at high concentrations, non-specific reactions of acetylated precursors and cysteine residues have been observed.² At low µM concentrations, these effects may be negligible but it is advisable to use a control compounds such as P-GlcNAc. Finally, P-GlcNAc may be used to boost intracellular GlcNAc levels. It has for example been shown that P-Neu5Ac can be used to boost intracellular neuraminic acid levels.³

• Applications

  Control compound for labeling/inhibition experiments utilizing acetylated glucosamine derivatives. P-GlcNAc4D, P-GlcNAc6Ac, P-GlcNAz, P-GlcNPoc, P-GlcNTFA

• Handling

  P-GlcNAc is soluble in a mixture of DMSO and PBS and is added to cell culture from a stock solution.

• Chemical Information

  CAS No.: 14086-90-9
  SMILES: O=C(C)OC1[C@H](NC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1
  Chemical formula: C₁₆H₂₃NO₁₀
  Molecular weight: 389.35
  Purity: > 95%
  Identity: ¹H NMR
  Shipping temperature: 20°C
  Storage temperature: -20°C