P-ManNPoc

Product information

• Function

  Metabolic labeling of sialoglycans for isolation, visualization and to improve Siglec binding. P-ManNPoc can also be converted into UDP-GlcNPoc in cells and incorporated to label GlcNAc residues.¹²

• Mode of action

  P-ManNPoc is passively taken-up by cells and incorporated in cell surface sialoglycans via the de novo biosynthesis pathway. P-ManNPoc contains a Poc group for “click” chemistry. Azide reagents can be reacted with the Poc group on live and fixed cells. 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. Since P-ManNPoc needs to traverse a longer intracellular biosynthesis pathway then labeling with sialic acid derivatives P-ManNPoc is less efficient and requires a higher concentration for labeling.¹ Also P-ManNPoc is somewhat toxic to cells at higher concentrations. If labeling via the de novo biosynthesis pathway is not a prerequisite we recommend the use of the more efficient and less toxic P-Neu5NPoc. In addition to sialic acid, P-ManNPoc has been shown to be converted to GlcNPoc inside cells resulting in the labeling of intracellular O-GlcNAc residues as well.²

• Applications

  Metabolic labeling of sialoglycans for isolation, visualization and to improve Siglec binding.¹²

• Handling

  P-ManNPoc is soluble in DMSO and PBS and is added to cell culture from a stock solution. Incubation of the cells with P-ManNPoc for 3 days in needed to achieve the maximal metabolic incorporation although a detectable signal is visible after 4 hrs.¹² Three days is needed to achieve the maximum turnover of sialylated glycans abd achieve maximal metabolic incorporation. Sialoglycans decorated with Neu5NPoc 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(OCC#C)N[C@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)OC1OC(C)=O
  Chemical formula: C₁₈H₂₃NO₁₁
  Molecular weight: 429.37
  Purity: > 95%
  Identity: ¹H NMR
  Shipping temperature: 20°C
  Storage temperature: 0°C