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The development of a modular approach to stereocontrolled oligosaccharide synthesis by intramolecular glycosylation

Ziel

It is now well established that oligosaccharides play fundamental roles in an enormously wide range of important biological processes, including viral and bacterial infectivity, antigenicity and cancer metastasis. In addition it also now recognized that th e post-translational modification of proteins by glycosylation plays a crucial role in successful protein folding, and on the conformation, metabolic stability and catalytic activity of folded glycoproteins. However in the vast majority of cases the functi on of the oligosaccharide is not yet precisely understood, and there is a need for synthetic oligosaccharides in order to elucidate the roles that these oligomers play in their varied environments. Despite impressive recent developments, no synthetic metho dology currently exists that allows the synthesis of oligosaccharides in a reliable and generally applicable manner. The research program we propose will centre on the further development of novel synthetic methodology for construction of synthetic oligosa ccharides, crucially in a totally stereoselective and potentially automatable fashion. The proposal centres on the development of a modular approach to sterecontrolled oligosaccharide synthesis. The crucial point is that whilst neighbouring group participa tion will be employed to give 1,2-trans glycosidic linkages using standard intermolecular glycosylation reactions, that by actually using the same building blocks we shall be able to achieve the stereoselective synthesis of 1,2-cis glycosidic linkages simp ly by performing intramolecular glycosylation reactions. Importantly both sets of reaction conditions will involve the same component steps, but by performing each of these individual steps in a different order we will be able to totally control the stereo chemical outcome of the glycosylation reaction. Such an approach would allow the development of the first oligosaccharide synthesiser wherein the problem of anomeric stereocontrol had been truly addressed.

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FP6-2002-MOBILITY-5
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