Synthesis of aryl azide chain-end functionalized N -linked glycan polymers and their photo-labelling of specific protein.

We report a straightforward synthesis of aryl azide chain-end functionalized N -linked glycan polymers and its application for affinity-assisted photo-labelling of specific protein. The aryl azide chain-end functionalized N -glycan polymers, including N -galactosyl, N -glucosyl, and N -lactosyl polymer, were synthesized from free glycan via glycosylamine intermediates followed by acrylation and polymerization via cyanoxyl-mediated free radical polymerization (CMFRP) in a one-pot fashion. The aryl azide chain-end functionalized N -glycan polymers were characterized by 1 H NMR and IR spectroscopy. The affinity-assisted photo-labeling capabilities of the aryl azide N -glycan polymers were demonstrated with aryl azide N -lactosyl polymer as a ligand for β-galactose-specific lectin from Arachis hypogaea (PNA) after UV irradiation and confirmed by SDS-PAGE with silver staining. Overall, the aryl azide chain-end functionalized N -linked glycan polymers will be useful multivalent ligands for specific protein labelling and functionality studies.