“Click-fluors”: Boronic acid-based saccharide sensors via CuAAC reaction

Zhai, Wenlei (2017). “Click-fluors”: Boronic acid-based saccharide sensors via CuAAC reaction. University of Birmingham. Ph.D.

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A series of mono- and bis-boronic acid compounds were synthesised via copper-catalysed azide-alkyne cycloaddition (CuAAC) reactions. The conditions of the CuAAC reaction were optimised across a range of substrates.

In chapter 2, the saccharide binding capacity of the synthesised mono-boronic acids (1\(^s\)\(^t\) and 2\(^n\)\(^d\) generation "click-fluors") were studied by fluorescence spectroscopy and isothermal titration calorimetry (ITC). The fluorescence studies of the synthesised boronic acids binding with D-fructose indicated that the triazole ring - boron acid distance has an obvious effect on the fluorescence response. The binding model of mono-boronic acids and D-fructose was investigated through \(^1\)H and \(^1\)\(^1\)B NMR titrations.

In chapter 3, study of the synthesised bis-boronic acid "click-fluors" showed the glucose binding affinity was improved by introducing an additional boronic acid group. Reducing the distance between two boronic acids was proven to be the key to achieve glucose selectivity. As a result, a fluorescent glucose selective bis-boronic acid sensor was successfully synthesised.

In chapter 4, a preliminary study was carried out as a proof-of-concept experiment of templated synthesis of glucose-selective sensors using "click chemistry".

Type of Work: Thesis (Doctorates > Ph.D.)
Award Type: Doctorates > Ph.D.
College/Faculty: Colleges (2008 onwards) > College of Engineering & Physical Sciences
School or Department: School of Chemistry
Funders: Other
Other Funders: China Scholarship Council, The University of Birmingham
Subjects: Q Science > QD Chemistry
URI: http://etheses.bham.ac.uk/id/eprint/7197


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