Well‐Defined Poly(N‐glycosyl 1,2,3‐triazole) Multivalent Ligands: Design, Synthesis and Lectin Binding Studies

Abstract

Glycopolymers have been synthesised by post-functionalisation of well-defined alkynefunctional polymers with sugar azides to yield N-glycosyl 1,2,3-triazole functional polymers. The Cu(I)-catalysed Huisgen cycloaddition was used to attach a-mannoside, bgalactoside and b-lactoside derivatives via an azide functionality bound directly to the sugar anomeric carbon. Three different catalytic systems were investigated for the click reactions; [(PPh 3 ) 3 Cu(I)Br], TBTA/Cu(I)Br and bathophenanthrolinedisulphonic acid disodium salt/Cu(I)Br. The latter of these was found to be the most efficient for the attachment of the larger/more sterically hindered disaccharide lactose moiety. The interaction of the lactose-and galactose-bearing glycopolymers with Ricinus Communis Agglutinin (RCA I) lectin was investigated by affinity HPLC analysis. The rate of the interaction between mannose polymer and concanavalin A (Con A) lectin was assessed by turbidimetry. The results from the lectin conjugation studies indicate that the glycopolymers prepared in this work are able to function as multivalent ligands, further suggesting that the attachment of the triazole directly to the sugar anomeric carbon has no significant effect on the interaction of these glycopolymers with Con A and RCA I.

Adhesion of Preosteoblasts and Fibroblasts onto Poly(pentafluorostyrene)‐Based Glycopolymeric Films and their Biocompatibility

“…The polymers were subsequently reacted with various sugar azides in the presence of copper to yield glycopolymers. [55][56][57][58][59] A similar approach was reported recently by Lee et. al.…”

A detailed study on understanding glycopolymer library and Con A interactions

“…In our group, we employed a facile approach to synthesize glycopolymers via the combination of copper mediated living radical polymerization (often called ATRP) and Huisgen copper(I)‐catalyzed azide–alkyne cycloaddition (CuAAC). Alkyne‐containing polymer scaffolds were prepared followed by modification of the polymer scaffolds with sugar azides …”

Poly(triazolyl methacrylate) glycopolymers as potential targeted unimolecular nanocarriers

“…36,37 Triazolyl methacrylate glycopolymers have been extensively investigated. 33,34,[38][39][40][41][42][43][44][45][46][47] Yet, to the best of our knowledge, this behaviour, suggestive of their surfactant-like properties and of their ability to non-covalently bind hydrophobic probes under aqueous conditions, has not been described. Thus, the present study investigates the mechanism and modalities of host-guest interactions between glycopoly- mers and low molecular weight guest-molecules.…”