P-Fuc

Product information

• Function

  P-Fuc is a control compound for labeling/inhibition experiments utilizing acetylated fucose derivatives such as P-Fuc2F, P-Fuc6Az, P-Fuc7Alk.

• Mode of action

  P-Fuc 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 fucose 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.¹ At low µM concentrations, these effects are likely negligible but it is advisable to use a control compounds such as P-Fuc. Finally, these lipophilic precursors may be used to boost intracellular monosaccharide levels. This has been demonstrated for cell permeable neuraminic acid derivative P-Neu5Ac.²

• Applications

  Control compound for labeling/inhibition experiments utilizing acetylated fucose derivatives (P-Fuc6Az, P-Fuc7Alk, P-Fuc2F). Potentially as a cell permeable derivative to boost intracellular fucose levels.

• Handling

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

• Chemical Information

  CAS No.: 64913-16-2
  SMILES: C[C@H]1[C@@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)C(OC(C)=O)O1
  Chemical formula: C₁₄H₂₀O₉
  Molecular weight: 332.30
  Purity: > 95%
  Identity: ¹H NMR
  Shipping temperature: 20°C
  Storage temperature: 20°C