Carbohydrates mediate a wide range of biological interactions, and understanding these processes benefits the development of new therapeutics and chemical biology research tools. Isolating sufficient quantities of carbohydrates and glycolipid from biological samples remains a significant challenge; as well as chemical synthesis which usually require multiple steps and purifications. Two methodologies, Regioselective Silyl Exchange Technology (ReSET) and glycosyl iodide glycosylation, have now been combined to simplify the synthesis of the globo series trisaccharide (globotriaose and isoglobotriaose) and a-lactosylceramide (a-LacCer). These glycoconjugates are tumor-associated carbohydrate antigens and immunostimulatory glycolipids that hold promise as potential immunotherapeutics. Glycosyl iodide can also be further functionalized by using trimethylene oxide (TMO) to introduce iodopropyl linker at the anomeric carbon as a chemical handle. The terminal iodide can be converted to corresponding azide followed by copper-catalyzed azide-alkyne cycloaddition to afford multivalent glycoconjugates of Gb3 for further investigation as anti-cancer vaccine.

Step-economical syntheses of tumor-associated carbohydrate antigens (TACAs) and immunogenic glycolipids using ReSET and glycosyl iodide gycosylation

248th National Meeting (2014)

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