Syntheses of Propargyl Glycosides of Disaccharides of the Capsular Polysaccharides from Serotypes 4, 7F, and 9V Useful for Glycoconjugate Vaccines.

We have developed a means of presenting relatively small glycans in a context to make them T cell-dependent antigens. This approach requires synthesis of glycans that remain close to carrier proteins upon conjugation, allowing T cell recognition and generation of B cells that produce high-affinity antibodies and memory toward target pathogens. In this work, we describe the syntheses of three disaccharides of the capsular polysaccharides from serotypes 4, 7F and 9V () as propargyl glycosides for use in this vaccine strategy.