Jump to main content
Jump to site search

Issue 8, 2016
Previous Article Next Article

Click-fluors”: triazole-linked saccharide sensors

Author affiliations

Abstract

A series of boronic acid-containing saccharide receptors was synthesised via copper catalysed azide–alkyne cycloaddition (CuAAC) reactions. Their saccharide binding capacity was studied by 1H and 11B NMR spectroscopy titrations and isothermal titration calorimetry (ITC) techniques. Fluorescent sensors were generated by linking a phenylboronic acid (PBA) receptor with fluorophores via a triazole-linker. Fluorescence titrations with fructose revealed that the substitution pattern about the PBA influences the fluorescence response to saccharides. Titrations studied by 1H NMR spectroscopy suggested that fructose binding is enhanced when the aromatic ring bearing the boronic acid has the triazole-containing substituent at the ortho position. No evidence of either a dative N–B bond or solvent insertion (between B and N) was observed by 11B NMR spectroscopy. These results demonstrate that synthetic accessible triazole receptors may allow rapid sensor synthesis, screening and discovery.

Graphical abstract: “Click-fluors”: triazole-linked saccharide sensors

Back to tab navigation

Supplementary files

Publication details

The article was received on 22 Apr 2016, accepted on 04 Jun 2016 and first published on 14 Jun 2016


Article type: Research Article
DOI: 10.1039/C6QO00171H
Author version
available:
Download author version (PDF)
Citation: Org. Chem. Front., 2016,3, 918-928
  • Open access: Creative Commons BY license
  •   Request permissions

    Click-fluors”: triazole-linked saccharide sensors

    W. Zhai, B. M. Chapin, A. Yoshizawa, H. Wang, S. A. Hodge, T. D. James, E. V. Anslyn and J. S. Fossey, Org. Chem. Front., 2016, 3, 918
    DOI: 10.1039/C6QO00171H

    This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
    • For reproduction of material from PCCP:
      [Original citation] - Published by the PCCP Owner Societies.
    • For reproduction of material from PPS:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
    • For reproduction of material from all other RSC journals:
      [Original citation] - Published by The Royal Society of Chemistry.

    Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Search articles by author

Spotlight

Advertisements