Organogel-assisted topochemical synthesis of multivalent glyco-polymer for high-affinity lectin binding

An organogelator, 2,4-undeca-diynyl-4′,6′-O-benzylidene-β-D-galactopyranoside, which aligns its diacetylene upon gelation, has been synthesized. UV irradiation of its gel resulted in topochemical polymerization of the gelator forming polydiacetylene (PDA). We have used this gel-state reaction for the synthesis of surface-immobilized multi-valent glycoclusters, which showed 1000-fold enhanced binding, compared to monomers, with various galactose-binding lectins.