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dc.contributor.advisorHulme, Alison N.
dc.contributor.advisorBradley, Mark
dc.contributor.authorLandi, Felicetta
dc.date.accessioned2011-08-01T10:15:10Z
dc.date.available2011-08-01T10:15:10Z
dc.date.issued2011-06-27
dc.identifier.urihttp://hdl.handle.net/1842/5021
dc.description.abstractThe recovery of the selected biological material in affinity-based separations relies on reversing the biological interaction responsible for the binding. General elution methods which are independent of the bioaffinity interaction have attracted increasing attention. The first three chapters of this thesis describe the development of a novel “click” functionalised azobenzene-based linker for affinity-independent elution protocols and the preliminary affinity studies using this linker. Ligands functionalised with a bioorthogonal propargyl label were readily attached to the terminal azide of the linker using the copper(I) catalysed Huisgen cycloaddition (or "click" reaction). Following separation, the linker was cleaved under mild non-denaturing conditions using Na2S2O4. In the last three chapters a novel approach towards the synthesis of the 4-methyl proline fragment of the cytotoxic natural product bisebromoamide (a potential affinity target) is proposed. For the pyrrolidine ring construction an enamide-olefin ring-closing metathesis (RCM) approach has been attempted. The installation of the required absolute stereochemistry has been achieved using a phase-transfer catalyst for the enantioselective alkylation of Schiff bases derived from glycine esters.en
dc.language.isoenen
dc.publisherThe University of Edinburghen
dc.relation.hasversionLandi, F.; Johansson, C. M.; Campopiano, D. J.; Hulme, A. N. Org. Biomol. Chem. 2010, 8, 56.en
dc.subjectaffinity-based separationsen
dc.subjectbioaffinity interactionen
dc.subjectclicken
dc.subjectbioorthogonal propargylen
dc.titleNew tools for target identification by affinity chromatographyen
dc.typeThesis or Dissertationen
dc.type.qualificationlevelDoctoralen
dc.type.qualificationnamePhD Doctor of Philosophyen


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