P-Neu5NPoc

Product information

• Function

  Unnatural sialic acid analog for metabolic labeling. Contains a Poc group for “click” chemistry. P-Neu5NPoc is passively taken-up by cells and incorporated in cell surface sialoglycans. Azide reagents can be reacted with the Poc group on live and fixed cells.¹ These azide 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 Beyond its application of P-Neu5NPoc for click chemistry, incorporation of this unnatural derivative also led to resistance to sialidases.³ This has been studied in the context of viral infection. In this study, the use of P-Neu5NPoc in host cells led to a decreased influenza infection by blocking its neuraminidase. In contrast, another derivative P-Neu5NAz is susceptible to neuraminidase cleavage and does not desturb sialoglycan turnover.

• Mode of action

  P-Neu5NPoc 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-Neu5NPoc 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-Neu5NPoc is soluble in DMSO and PBS and is added to cell culture from a stock solution. Incubation of the cells with P-SiaPoc 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(OCC#C)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: C₂₄H₃₁NO₁₅
  Molecular weight: 573.17
  Purity: > 95%
  Identity: ¹H NMR
  Shipping temperature: 20°C
  Storage temperature: -20°C