Abstract
This thesis consists of two parts. In the first half, an anthracene tetra-lactam based receptor previously designed to bind carbohydrates was found to bind biologically relevant molecules such as purines with high affinity. An investigation into its binding profile and mechanism of binding was subsequently conducted, elucidating association constants through fluorescence and NMR spectroscopy as well as isothermal titration calorimetry. Encouragingly, an investigation into the nature of the binding mode of this receptor with the various guests showed that hydrogen bonding directly contributed to the binding affinity, to our knowledge this is the first time this phenomenon has been conclusively shown, evidenced through 1H NMR spectroscopic data.In the second half, the design of a receptor based on a hexa-urea scaffold designed to bind β glucose was modified in attempts to switch selectivity away from all equatorial carbohydrates towards the axially substituted mannose and galactose. Diversion from an established synthetic route allowed installation of a triazole ring through click chemistry. In a final study, a second and third set of spacer units were developed to allow access to a library of receptors containing thioether linkages. Molecular modelling of the receptor architectures showed promise, with the receptors having excellent complementarity for axially substituted monosaccharides. Initial binding studies with the monosaccharides mannose and galactose showed that the previous selectivity for glucose had indeed been shifted towards axially substituted sugars.
| Date of Award | 27 Sept 2022 |
|---|---|
| Original language | English |
| Awarding Institution |
|
| Supervisor | Anthony P Davis (Supervisor) |
Cite this
- Standard