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 α-mannopyranoside azide was then clicked onto the bead to give a mannose functionalized Rasta resin. IR, gel-phase 1H 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.

Porous polymer particles—A comprehensive guide to synthesis, characterization, functionalization and applications

“…Although there are numerous studies on CuAAC functionalization of nonporous polymers [280,298,328,[336][337][338][339][340][341][342][343][344][345][346][347][348][349][350][351], silica [352][353][354] and metal particles [355], the amount of publications on porous polymer particles is limited. Finn et al [356] described the click functionalization of a commercial porous agarose resin for affinity chromatography.…”

Synthesis and characterization of a new series of rigid polytriazole resins

“…[6][7][8][9][10] In recent years, many researchers dedicated to use CuAAc reaction to synthesize polymers in the field of material, [11][12][13][14] biological, [15,16] and pharmaceutical. [17,18] Our laboratory has been engaged in developing novel polytriazole (PTA) resins with low temperature curing and high heat-resistance ten years ago.…”

Construction of Linear Polymers, Dendrimers, Networks, and Other Polymeric Architectures by Copper‐Catalyzed Azide‐Alkyne Cycloaddition “Click” Chemistry

“…CuAAC has repeatedly been shown to be an efficient way to functionalize solid supports. [48][49][50][51][52][53][54] For example, Santoyo-Gonzalez and coworkers convergently prepared glyco-dendrimers with a silica core and demonstrated their effectiveness as materials for affinity chromatography separation of proteins (Scheme 11). [55] A particularly interesting combination of CuAAC and ATRP for the synthesis of polymeric dendrimers was introduced by Monteiro and coworkers.…”