P-Neu5NAz

Product information

• Function

  Unnatural sialic acid analog for metabolic labeling. Contains a Azide group for “click” chemistry. P-Neu5NAz is passively taken-up by cells and incorporated in cell surface sialoglycans. Alkyne reagents can be reacted with the Azide group on live and fixed cells.¹ These azides can be modified with an affinity tag or fluorophore for example. Small molecules can also be attached to enhance the binding to Siglec receptors.² In contrast to P-Neu5NPoc, P-Neu5NAz residues can be cleaved by sialidases and hence minimally perturb the turnover of Neuraminic acids.³ This has been studied in the context of viral infection. In this study, the use of P-Neu5NAz in host cells did to lead to a decreased influenza infection by blocking its neuraminidase whereas use of P-Neu5NPoc did.

• Mode of action

  P-Neu5NAz is passively taken-up by mammalian cells and converted into its CMP-SiaPoc derivative. This is used as a donor substrate for sialyltransferase enzymes and transferred to O-, N-glycans and glycolipids. P-Neu5NAz is a much more efficient metabolic label of sialic acid than ManNAc based derivative and also less toxic.¹, ⁴

• Applications

  Metabolic labeling of sialoglycans for isolation, visualization and to improve Siglec binding

• Handling

  P-SiaNAz is soluble in DMSO and PBS and is added to cell culture from a stock solution. Incubation of the cells with P-SiaNAz for 3 days in needed to achieve the maximal metabolic incorporation. Three days is needed to achieve the turnover of sialylated glycans to achieve maximal metabolic incorporation.

• Chemical Information

  CAS No.: NA
  SMILES: O=C(CN=[N+]=[N-])N[C@H]1[C@H]([C@H](OC(C)=O)[C@H](OC(C)=O)COC(C)=O)OC(C(OC)=O)(OC(C)=O)C[C@@H]1OC(C)=O
  Chemical formula: C₂₂H₃₀N₄O₁₄
  Molecular weight: 574.18
  Purity: > 95%
  Identity: ¹H NMR
  Shipping temperature: 20°C
  Storage temperature: 0°C