Neu5Ac9Az

Product information

• Function

  Neu5Ac9Az is a metabolic labeling reagent to probe the incorporation of sialic acid residues into cell surface glycans. Sialic acid, or N-acetylneuraminic acid, are expressed at the termini of cell surface glycans.¹

• Mode of action

  Neu5Ac9Az is added to cell culture in high concentrations (1-3 mM) to be taken up in cells. Once taken up, Neu5Ac9Az is converted into CMP-Neu5Ac9Az and transferred onto glycoproteins and which are subsequently shuttled to the cellular membrane. It was shown that CMP-Neu5Ac9Az is not converted to CMP-Neu5Gc9Az even in cell line that do express CMAH.¹ Neu5Ac9Az contains an azide group for “click” chemistry. Alkyne reagents can be reacted with the azide group on live and fixed cells. These alkynes can be modified with an affinity tag or fluorophore for example. Neuraminic acid labeling in mice has been achieved with Neu5Ac9Az and a liposome carrier for delivery.¹²

• Applications

  Metabolic labeling of sialoglycans for isolation and visualization.

• Handling

  Neu5Ac9Az is soluble in water and PBS and is added to cell culture from a stock solution. A click chemistry based assay can be used to measure the extent of Neu5Ac9Az incorporation. For this purpose, Neu5Ac9Az and a suitable biotin probe can be used. Please see our click chemistry page for suitable reaction partners.

• Chemical Information

  CAS No.: 76487-51-9
  SMILES: OC1(C(O)=O)C[C@H](O)[C@@H](NC(C)=O)[C@H]([C@H](O)[C@H](O)CN=[N+]=[N-])O1
  Chemical formula: C₁₁H₁₈N₄O₈
  Molecular weight: 334.29
  Purity: > 95%
  Identity: ¹H NMR
  Shipping temperature: 20°C
  Storage temperature: -20°C