P-BnGalNAc

Product information

• Function

  P-BnGalNAc is a decoy substrate for the biosynthesis of O-linked glycans based on O-GalNAc. It can be used to inhibit the biosynthesis of membrane linked O-GalNAc containing glycans. Instead cells produce and excrete glycans attached to the BnGalNAc decoy substrate which can be analyzed with mass spectrometry. P-BnGalNAc works the same as BnGalNAc but is more cell permeable and hence active at a lower concentration.

• Mode of action

  O-linked glycans based on α-O-GalNAc residues starts with the addition of α-O-GalNAc residues to serine or threonine side chains. Next, additional sugars are added to the α-O-GalNAc residue. P-BnGalNAc is a cell permeable derivative of GalNAc. It enters cells and, and is deacetylated by esterases to afford BnGalNAc. BnGalNAc acts as a decoy substrate. Instead of adding monosaccharides to α-O-GalNAc glycoproteins, these residues are added to BnGalNAc. The corresponding glycoconjugates are excreted into the cell medium and the synthesis of mucins and other glycoconjugates based on α-O-GalNAc is inhibited. In a direct comparison with BnGalNAc, P-BnGalNAc showed inhibition at concentration of 50 µM whilst BnGalNAc required concentration > 250 µM as is not taken up by cells as efficiently.

• Applications

  P-BnGalNAc has been used to study the structure of mucins by mass spec analysis of the excreted glycans grafted on BnGalNAc. It was shown that the structure of the glycans grafted on P-BnGalNAc depended on the concentration of P-BnGalNAc.

• Handling

  P-BnGalNAc is soluble in DMSO/ PBS and added to cells in from a stock solution. Good priming/inhibition is achieved at 50 µM concentration.

• Chemical Information

  CAS No.: 141019-71-8
  SMILES: O=C(O[C@@H]1[C@H](OC(C)=O)[C@@H](NC(C)=O)[C@@H](OCC2=CC=CC=C2)O[C@@H]1COC(C)=O)C
  Chemical formula: C₂₁H₂₇NO₉
  Molecular weight: 437.44
  Purity: > 95%
  Identity: ¹H NMR
  Shipping temperature: 20°C
  Storage temperature: 20°C