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Saccharide recognition : boronic acids as receptors in polymeric networks ; Zuckererkennung in polymeren Netzwerken mittels Boronsäuren als Rezeptoren
In this thesis entitled “Saccharide Recognition - Boronic acids as Receptors in Polymeric Networks” different aspects of boronic acid synthesis, their analysis and incorporation or attachment to different polymeric networks and characterisation thereof were investigated. The following key aspects were considered: • Provision of a variety of different characterised arylboronic acids and benzoboroxoles • Attachment of certain derivatives to nanoparticles and the characterisation of saccharide binding by means of isothermal titration calorimetry and displacement assay (ARS) to enhance the association constant to saccharides at pH 7.4 • Enhancement of selectivity in polymeric systems by means of molecular imprinting using fructose as template and a polymerisable benzoboroxole as functional monomer for the recognition at pH 7.4 (Joined by a diploma thesis of F. Grüneberger) • Development of biomimetic saccharide structures and the development of saccharide (especially glucose and fructose) binding MIPs by using these structures as template molecules. In the first part of the thesis different arylboronic acid derivatives were synthesised and their binding to glucose or fructose was investigated by means of isothermal titration calorimetry (ITC). It could be derived, which is in parallel to the literature, that derivatives bearing a methylhydroxyl-group in ortho-position to the boron (benzoboroxole) exhibit in most cases a two-fold higher association constant compared to the corresponding phenylboronic acid derivative. To gain a deeper understanding NMR spectroscopy and mass spectrometry with the benzoboroxole and glucose or fructose was performed. It could be shown that the exchange rate in terms of NMR time scale is quite slow since in titration experiments new peaks appeared. Via mass spectrometry of a mixture between benzoboroxole and glucose or fructose, different binding stoichiometries could be detected showing that the binding of saccharides is comparable with their binding to phenylboronic acid. In addition, ...
Saccharide recognition : boronic acids as receptors in polymeric networks ; Zuckererkennung in polymeren Netzwerken mittels Boronsäuren als Rezeptoren
In this thesis entitled “Saccharide Recognition - Boronic acids as Receptors in Polymeric Networks” different aspects of boronic acid synthesis, their analysis and incorporation or attachment to different polymeric networks and characterisation thereof were investigated. The following key aspects were considered: • Provision of a variety of different characterised arylboronic acids and benzoboroxoles • Attachment of certain derivatives to nanoparticles and the characterisation of saccharide binding by means of isothermal titration calorimetry and displacement assay (ARS) to enhance the association constant to saccharides at pH 7.4 • Enhancement of selectivity in polymeric systems by means of molecular imprinting using fructose as template and a polymerisable benzoboroxole as functional monomer for the recognition at pH 7.4 (Joined by a diploma thesis of F. Grüneberger) • Development of biomimetic saccharide structures and the development of saccharide (especially glucose and fructose) binding MIPs by using these structures as template molecules. In the first part of the thesis different arylboronic acid derivatives were synthesised and their binding to glucose or fructose was investigated by means of isothermal titration calorimetry (ITC). It could be derived, which is in parallel to the literature, that derivatives bearing a methylhydroxyl-group in ortho-position to the boron (benzoboroxole) exhibit in most cases a two-fold higher association constant compared to the corresponding phenylboronic acid derivative. To gain a deeper understanding NMR spectroscopy and mass spectrometry with the benzoboroxole and glucose or fructose was performed. It could be shown that the exchange rate in terms of NMR time scale is quite slow since in titration experiments new peaks appeared. Via mass spectrometry of a mixture between benzoboroxole and glucose or fructose, different binding stoichiometries could be detected showing that the binding of saccharides is comparable with their binding to phenylboronic acid. In addition, ...
Saccharide recognition : boronic acids as receptors in polymeric networks ; Zuckererkennung in polymeren Netzwerken mittels Boronsäuren als Rezeptoren
Schumacher, Soeren (author)
2011-07-11
Theses
Electronic Resource
English
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