A modular click approach to glycosylated polymeric beads: Design, synthesis and preliminary lectin, recognition studies

Abstract

Covalent immobilization of a range of carbohydrate derivatives onto polymeric resin beads is described. Copper-catalyzed Huisgen [2 + 3] cycloaddition (often termed click chemistry) was used to graft mannose-containing azides to complementarily functionalized alkyne surfaces, namely (a) Wang resin or (b) Rasta particles consisting of a clickable alkyne polymer loose outer shell and a Wang resin inner core. For the second approach, Wang resin beads were first converted into immobilized living radical polymerization initiators with subsequent polymerization of trimethylsilanyl-protected propargyl methacrylate followed by deprotection with TBAF to yield the desired polyalkyne clickable scaffold. The appropriate (x-mannopyranoside azide was then clicked onto the bead to give a mannose functionalized Rasta resin. IR, gel-phase H-1 NMR, and elemental analysis have been used to characterize the modified resins. The binding abilities of these D-mannose-modified particles were subsequently tested using fluorescein-labeled Concanavalin A (Con A), a lectin that binds certain mannose-containing molecules. Preliminary results indicated that the novel glyco-hybrid materials presented in this work are able to efficiently recognize mannose-binding model lectins such as Con A, opening the way for their potential application in affinity chromatography, sensors, and other protein recognition/separation fields.