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dc.contributor.authorCorcilius, Leo
dc.date.accessioned2016-12-06
dc.date.available2018-06-15
dc.date.issued2016-07-18
dc.identifier.urihttp://hdl.handle.net/2123/16017
dc.description.abstractThis thesis describes efforts towards the stereoselective synthesis of homogeneous plant and animal-derived O-linked glycopeptides for the purposes of interrogating structure-function relationships. The first section of this thesis (chapter 2) details the synthesis of novel CLE and CEP glycopeptide plant hormones which bear the plant-specific β1,2-triarabinosylated hydroxyproline motif. The hormones which were synthesised have been linked to the root growth programme in legumes (Medicago truncatula and Soybean), but have not previously been structurally characterised. One of these glycopeptides, MtCLE13, was biologically evaluated and was shown to possess nodulation inhibiting properties only when triarabinosylated at the key hydroxyproline residue, thus confirming the critical functional role of the carbohydrate moiety. The second section of this thesis (chapters 3-5) describes efforts towards the stereoselective synthesis of human cell membrane-derived MUC1 glycopeptides containing α-sialylated tumour-associated carbohydrate antigens (sialyl Tn, 2,6-sialyl T, 2,3-sialyl T and glycophorin antigens). The work described in these chapters culminated in the development of a divergent and highly stereoselective synthetic route to all of the key glycosylamino acids required for the construction of a library of homogeneous glycopeptide cancer vaccine candidates.en_AU
dc.rightsThe author retains copyright of this thesis. It may only be used for the purposes of research and study. It must not be used for any other purposes and may not be transmitted or shared with others without prior permission.en_AU
dc.subjectstereoselectiveen_AU
dc.subjectglycosylationen_AU
dc.subjectCLEen_AU
dc.subjectCEPen_AU
dc.subjectMUC1en_AU
dc.subjectIADen_AU
dc.titleStereoselective Synthesis of Plant and Animal-Derived O-linked Glycopeptidesen_AU
dc.typeThesisen_AU
dc.date.valid2016-01-01en_AU
dc.type.thesisDoctor of Philosophyen_AU
usyd.facultyFaculty of Science, School of Chemistryen_AU
usyd.degreeDoctor of Philosophy Ph.D.en_AU
usyd.awardinginstThe University of Sydneyen_AU


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