Synthesis towards defined oligosaccharides for functional genomic studies of the primary plant cell wall
Neves, James Edward
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This thesis describes the synthetic preparation of a set of oligosaccharides found in the glycostructures of the primary plant cell wall. These oligosaccharides will be used in immunocompetition assays in order to characterize the binding specificities of monoclonal antibodies generated against cell wall extracts. Additionally, these compounds can be used for the generation of monoclonal antibodies. An orthogonally protected trisaccharide 24 was prepared that allowed direct access to target 1 and for the selective deprotection of the C-2, C-3, and C-6 hydroxyl moieties of the non-reducing terminal galactoside, providing an efficient route to the tetrasaccharide targets 2, 3, and 4. However, an alternate, less convergent route using three different trisaccharides was found to be necessary. The orthogonal Fmoc, levulinoyl, and benzylidene acetal protecting groups were utilized. Also, Ph2SO/Tf2O was used as a powerful promoter system in glycosylation reactions.