Give Me Some Sugar: Synthesis of New Carbohydrate Mimics

Carbohydrates are among the most abundant class of biomolecules with a variety of derivatives. The goal of this research project is to synthesize unexplored glucose derivatives for future studies of their biological functions. The specific area of focus will be on 6→6 linked and 1→6 linked sugar analogs bound by an ester functional group. These sugar derivatives will be made by chemically connecting two sugar molecules, in a reaction called glycosylation. Tri-O-acetyl-β-glucopyranurono-6,1-lactone will be used as the starting material for all the glycosylation reaction. The lactone has been successfully synthesized by protecting the hydroxy groups of glucuronic acid with acetyl groups to ensure reactivity at the carboxyl site only. The protected glucuronic acid was then transformed into the desired glucopyranurono- 6,1-lactone. Reaction conditions were optimized by reacting cyclohexylmethanol and tetrahydropyran-2-methanol with the lactone to make 6,6-glucopyranosyl-cylcohexyl and 6,6- glucopyranosy-tetrahydropyranyl, respectively. These simple glucose derivatives were be purified by column chromatography and characterized by NMR. In the future, we intend to use the optimized reaction conditions for the synthesis of more complex polyhydroxylated disaccharides. In this poster, we will present preliminary data on the synthesis of 6→6-linked glucose derivatives, as well as proposed future work for the synthesis of more complex sugar analogs