Carbohydrate manipulations towards high-mannose oligosaccharides

Identifier:  TDX:1109

Handle: https://hdl.handle.net/20.500.11797/TDX1109

Authors:  Castilla López, Javier

Abstract:
The final goal of this thesis is the development of strategic methods fro the synthesis of well-defined 1,2-linked oligosaccharides and S-linked thio-analogues through different polymerization techniques. These structures form a complex group of biomolecules with an unsurpassed structural diversity, performing a variety of biological functions. In this context, the present work aimed to develop new procedures in carbohydrate chemistry, focusing in the oligomerization reactions. Thus, efficient syntheses have been studied for accessing the suitable carbohydrate based monomers (including epoxides, episulfides, carbonates and tiocarbonates). Unexpectedly, the synthesis of epithiocarbohydrates afforded carbohydrate-derived 1,3-oxazolidine-2-thiones. These compounds have proved to be quite attractive as new enzyme inhibitors for Gaucher disease. All enzyme inhibition studies can be found in the manuscript.