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

J. Norman, S. Tommasone, P.m. Mendes

Research output: Contribution to journalArticlepeer-review

Abstract

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.
Original languageEnglish
Article number100939
JournalMaterials Today Chemistry
Volume24
Early online date14 May 2022
DOIs
Publication statusPublished - 1 Jun 2022

Keywords

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

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