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Title: Anthracene based synthetic lectins
Author: Destecroix , Harry
ISNI:       0000 0004 5924 3103
Awarding Body: University of Bristol
Current Institution: University of Bristol
Date of Award: 2015
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Over the past 40 years there has been substantial interest in continuous glucose monitors (CGMs) for diabetes management. Much of the work has focused on the use of enzymes, lectins (carbohydrate binding proteins) or boronic acids as the sensing element, but instability and biocompatibility has hindered development. This has presented an 0pp0l1unity for supramolecular chemists to make synthetic lectins for glucose that respond in real time to glucose in the blood. However, carbohydrate recognition in water presents a challenge due to the hydromimetic nature of the substrate. Moreover, subtle structural differences between monosaccharides makes selectivity problematic. Despite these difficulties, our group has met with some success in designing synthetic lectins over the past decade. Recently we reported a simple monocyclic receptor An-L 34 for glucose which is accessible in only 5 steps with 23% overall yield. The receptor binds glucose with excellent selectivity over physiological blood glucose levels, displaying increases in fluorescence emission suggesting its potential as a CGM. We report the development of a series of receptors based on the new architecture. New synthetic procedures have provided access to asymmetrical systems that have highlighted the driving forces behind binding. 2nd and 3rd generation dendritic solubilising groups have been synthesised leading to receptors that are less prone to aggregation and with enhanced affinity for glucose and improved optical properties for sensing. The improvements are attributed to the interaction of the carboxylate groups with the sugar from the larger solubilising groups. Using this approach a new receptor with 100 fold selectivity for positively charged monosaccharide glucosamine has been demonstrated. The new generation systems have been screened in human blood plasma, with the 2nd generation systems showing enhancements in response to glucose. Furthermore work has started towards immobilisation of receptors for fibre optic sensing.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available