Neu5Ac3F

Product information

• Function

  Neu5Ac3F inhibits the sialic acid biosynthesis. It is a global sialylation inhibitor which inhibits the formation of all sialic acid types. It blocks the action of sialyltransferase enzymes. Neu5Ac3F needs to be taken up via a sialic acid transporter. Neu5Ac3F is not taken-up at µM concentrations in mammalian cells since these lack an active transport mechanism. If inhibition of sialylation via passive diffusion is desired, we recommend the use of P-Neu5Ac3F which is taken up via passive diffusion

• Mode of action

  Neu5Ac3F is a metabolic pro-drug. It enters cells via active uptake by the transport system in NTHi (non-typeable Haemophilus influenzae) and is converted to the active inhibitor, CMP-Neu5Ac3F inside NTHi cells. This compound blocks the action of sialyltransferase enzymes and prevents the sialylation of the lipooligosaccharide in NHTi.¹ Neu5Ac3F is not taken-up at µM concentrations in mammalian cells since these lack an active transport mechanism. If inhibition of sialylation via passive diffusion is desired, we recommend the use of P-Neu5Ac3F which is taken up via passive diffusion.

• Applications

  Neu5Ac3F is a very good alternative for experiments with Sialidase. Often these enzymes are of bacterial origin and hence easily contaminated, Neu5Ac3F is chemically pure. Furthermore, the effect of a sialidase treatment is short-lived as the cells quickly reproduce sialylated glycans, Neu5Ac3F induces a prolonged suppression of sialylation. Neu5Ac3F has been used to investigate the role of sialylation in NTHi infections in vitro.¹

• Handling

  Neu5Ac3F is soluble in water and PBS and is added to cell culture from a stock solution. Desialylation can be assayed with SNA and MALII lectins binding to α-2,6 and α-2,3 linked sialic acids, respectively. Alternatively, a click chemistry based competitive assay can be used to measure the extent of cellular sialylation in NTHi. For this purpose Neu5NAz or Neu5NPoc and a suitable biotin probe can be used.

• Chemical Information

  CAS No.: 921-40-4
  SMILES: OC1(C(O)=O)[C@H](F)[C@H](O)[C@@H](NC(C)=O)[C@H]([C@H](O)[C@H](O)CO)O1
  Chemical formula: C₁₁H₁₈FNO₉
  Molecular weight: 327.26
  Purity: > 95%
  Identity: ¹H NMR
  Shipping temperature: 20°C
  Storage temperature: -20°C