XylNap

Product information

• Function

  XylNap is a decoy substrate for the glycosaminoglycan (GAG) biosynthesis. It acts as a decoy substrate of the endogenous glycosaminoglycan synthesis. Instead of priming GAGs on O-linked xylose residues, GAG synthesis is primed on XylNap. GAGs primed on XylNap are excreted.

• Mode of action

  GAGs are connected to the core protein via an O-linked Xylose residue. The biosynthesis of GAGs starts with the addition of Xylose to a serine side chain. Next, a Galactose residue is installed in β-1,4 fashion onto the Xylose residue followed by further elongation to afford GAG chains. XylNap is taken up by cells via passive diffusion and acts as a decoy substrate for the β-1,4 galactosyl transferase in cells and primes the synthesis of GAG chains on XylNap. Since the chains are connected to XylNap and not a protein the GAG-XylNap chains are excreted. At sufficient concentrations of XylNap, GAG synthesis on O-linked xyloside is inhibited and instead synthesis take place almost exclusively on the XylNap decoy. It has been shown that XylNap primes heparan sulfate (HS) and chondroitin sulfate/dermatan sulfate (CS/DS) biosynthesis and hence inhibits the biosynthesis of GAGs carrying these chains. Next to XylNap, we also offer XylPNP which acts in a similar manner. A comparative study found that the hydrophobicity and concentration of these compounds influenced the ratio of HS/CD,DS priming.¹ From this study it follows that the hydrophobicity order is XylPNP < XylNap and that the proportion of HS priming increases with increasing hydrophobicity.

• Applications

  XylNap is a cell permeable inhibitor of GAG synthesis. The excreted GAG-XylNap constructs are excreted from the cell and can be isolated an analyzed. These compounds are of particular interest for the study of the role of GAGs in cancer but are also used to study diseases related to defects in the break-down of GAGs.²

• Handling

  XylNap is soluble in DMSO/water and added to cells in this form (final concentration DMSO 0.5% max). Good priming is achieved at 100µM – 1mM concentration.

• Chemical Information

  CAS No.: NA
  SMILES: O[C@H]1[C@H](O)[C@@H](O)[C@H](OC2=CC=C(C=CC=C3)C3=C2)OC1
  Chemical formula: C₁₅H₆O₅
  Molecular weight: 276.28
  Purity: > 95%
  Identity: ¹H NMR
  Shipping temperature: 20°C
  Storage temperature: -20°C