In this study, "click chemistry" was used to assemble a collection of potential glycosidase inhibitors. Using different "click chemistry" conditions, 21 α-D- and β-D glucopyranosyl triazoles were synthesised and assayed as inhibitors of sweet almond β-glucosidase and yeast α-glucosidase. A set of moderately effective glycosidase inhibitors was identified. In the course of this work significant differences in the reactivity of the α- and β-glucopyranosyl azides under CuAAC conditions was noted. This matter was investigated by X-ray crystallography and, in keeping with the anomeric effect, pointed to a difference in partial charge distribution in the azide and sugar moieties. Starting from maltosyl and maltotriosyl azides another collection of 12 triazoles was synthesised and all of the libraries were assayed against starch degrading enzymes from barley. A moderate inhibitor of α-glucosidase was identified, as were several weak inhibitors of β-amylase.
| Identifer | oai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:502211 |
| Date | January 2009 |
| Creators | Dedola, Simone |
| Publisher | University of East Anglia |
| Source Sets | Ethos UK |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
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