P-ManNAz

Product information

• Function

  Metabolic labeling of sialoglycans for isolation, visualization and to improve Siglec binding. P-ManNAz can also be converted into UDP-GlcNAz in cells and incorporated to label GlcNAc residues.¹

• Mode of action

  P-ManNAz is passively taken-up by cells and incorporated in cell surface sialoglycans via the de novo biosynthesis pathway. P-ManNAz contains an azide group for “click” chemistry. Alkyne reagents can be reacted with the azide group on live and fixed cells. This alkyne can be modified with an affinity tag or fluorophore for example. Small molecules can also be attached to enhance the binding to Siglec receptors. Since P-ManNAz needs to traverse a longer intracellular biosynthesis pathway then labeling with sialic acid derivatives P-ManNAz is less efficient and requires a higher concentration for labeling.¹ If labeling via the de novo biosynthesis pathway is not a prerequisite we recommend the use of the more efficient and less toxic P-Neu5NAz.

• Applications

  Metabolic labeling of sialoglycans for isolation, visualization and to improve Siglec binding.¹

• Handling

  P-ManNAz is soluble in DMSO and PBS and is added to cell culture from a stock solution. Incubation of the cells with P-ManNAz for 3 days in needed to achieve the maximal metabolic incorporation although a detectable signal is visible after 4 hrs.¹ Three days is needed to achieve the maximum turnover of sialylated glycans abd achieve maximal metabolic incorporation. Sialoglycans decorated with Neu5NAz residues can be used to perform “click” chemistry. Please see our click chemistry page for suitable reaction partners.

• Chemical Information

  CAS No.: 1431120-36-3
  SMILES: O=C(CN=[N+]=[N-])N[C@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)OC1OC(C)=O
  Chemical formula: C₁₆H₂₂N₄O₁₁
  Molecular weight: 430.37
  Purity: > 95%
  Identity: ¹H NMR
  Shipping temperature: 20°C
  Storage temperature: -20°C