期刊
ORGANIC CHEMISTRY FRONTIERS
卷 3, 期 8, 页码 918-928出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6qo00171h
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资金
- University of Birmingham
- Royal Society
- EPSRC [EP/J003220/1]
- Royal Society International Joint Project Scheme
- Welch Regents Chair [F-0046]
- 39 China Scholarship Council (CSC)
- Engineering and Physical Sciences Research Council [EP/J003220/1, DT/F00267X/1] Funding Source: researchfish
- EPSRC [DT/F00267X/1] Funding Source: UKRI
A series of boronic acid-containing saccharide receptors was synthesised via copper catalysed azidealkyne cycloaddition (CuAAC) reactions. Their saccharide binding capacity was studied by H-1 and B-11 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 H-1 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 B-11 NMR spectroscopy. These results demonstrate that synthetic accessible triazole receptors may allow rapid sensor synthesis, screening and discovery.
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