Date of Award
Doctor of Philosophy
Nicola L. B. Pohl
In order to provide a strategy which could produce the biologically important beta-mannans in a highly efficient and economical way, this dissertation illustrates the development of the automated solution-phase synthesis of different beta-mannans including the fungal beta-1,2-mannans by using both oxidation-reduction and beta-directing mannuronate strategies, and also reveals a new strategy for beta-mannan synthesis by reduction of mannuronate esters to alcohols. The following chapter shows the power of this automated solution-phase method to create beta-1,4-mannuronate and beta-1,4-mannan oligomers up to hexasaccharides. The subsequent chapter demonstrates the application of this new beta-mannan synthesis strategy for the synthesis of the insect N-glycan terminal trimannosides for fluorous microarray and isothermal titration calorimetry (ITC) studies to investigate the binding affinity of the pea enation mosaic virus (PEMV) in the aphid digestion system for clues to the virus transmission pathway of the virus in these notorious pests. Finally, the automated solution-phase synthesis of beta-1,6-mannan and beta-1,3-mannan oligomers presents the scope of the automated solution-phase synthesis of beta-mannans and its potential for synthesizing other oligosaccharides containing this challenging linkage.
Tang, Shu-Lun, "Automated solution-phase synthesis of β-mannans" (2012). Graduate Theses and Dissertations. 12481.