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    Selective oligosaccharide recognition with phenylboronic acid through Cu(I)-catalysed click imprinted surfaces

    Year: 2022

    Journal: Mater. Today Chem., Volume 24, JUN

    Authors: Norman, J.; Tommasone, S.; Mendes, P. M.

    Organizations: EPSRC [EP/K027263/1]; ERC [874966, 614787]; Prostate Cancer UK [RIA17-ST2-020]

    Keywords: Molecular imprinting; Copper(I)-catalysed click reaction; Saccharide recognition; Boronic acid; Self -assembled monolayers

    With the emerging role of glycans as potential diagnostic markers of disease, highly selective diagnostic platforms must be developed to realise the clinical value of irregular glycan expression patterns. Overcoming chemical and structural homogeneity between oligosaccharide structures however remains a significant challenge, which largely rests on the capability to develop materials embedding precise carbohydrate recognition. Herein we report a surface imprinting strategy that takes advantage of the high yield Cu(I)-catalysed azide-alkyne cycloaddition (CuAAC) click reaction to achieve oligosaccharide imprinted cavities featuring precisely organized phenylboronic acid (PBA) motifs. Central to the construction of the imprinted surface was the choice of a foundation alkyne-terminated monolayer of a long alkyl chain to impart a high surface click efficiency of the PBA motif. By pre-forming and clicking an oligosaccharide:PBA complex onto the alkyne-terminated monolayer and capping the free space, selective oligosaccharide imprinted cavities were formed with low millimolar dissociation constants.(c) 2022 The Author(s). Published by Elsevier Ltd. This is an open access article under the CC BY license (http://creativecommons.org/licenses/by/4.0/).
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