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Title: Synthetic lectins with novel selectivity
Author: Howgego, Joshua David
ISNI:       0000 0004 2738 8674
Awarding Body: University of Bristol
Current Institution: University of Bristol
Date of Award: 2012
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Carbohydrates are the most plentiful organic molecules on the surface of the earth and also some of the most complex. They are not just fuel sources, but also function as identifying markers for cells, on the surfaces of which they reside in the form of glycoconjugates. These identifying molecules are recognised by lectins; proteins which bind carbohydrates through non-covalent interactions. This recognition mediates a whole range of important biological processes, from fertilisation to infection with pathogens. 'Synthetic lectins' in the context of this thesis are artificially designed and synthesised organic receptor molecules. They bind sugars in aqueous environments through non-covalent interactions and as such may be considered biomimetic in the strictest sense. Synthetic lectins designed according to the 'temple' principles developed in the Davis group have so far been successful in binding sugars which have all their hydroxyl groups orientated equatorially, such as glucose. In this thesis the problem of how to design synthetic lectins for monosaccharides with less uniform distribution of functionality (for example mannose or galactose) is explored. To that end the synthesis of receptors 1 - 3 is described. Characterisation of the binding behaviour of these molecules reveals new patterns of selectivity; for example, disaccharides are bound in preference to monosaccharides. Receptor 4 shows a small but significant affinity for N-acetylneuraminic acid. This substrate is of widespread importance in physiological signalling, and few artificial receptors have previously bound this substrate in water through purely non-covalent interactions.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available