Trypanosoma cruzi is the causative agent of Chagas disease, affecting 16-18 million people annually, with no effective vaccine available. This protozoan parasite expresses cell surface oligosaccharides with terminal alpha-galactosyl and rhamnosyl residues, whose chemical structures are being investigated through syntheses and immunological studies. This led to the discovery of a new orthogonal protecting group manipulation method, and employed a regioselective glycosylation method to synthesize a trisaccharide with potential immunogenicity.  Our saccharides were equipped with a thiol functionality and conjugated to maleimide-derivatized KLH (Keyhole Limpet Hemocyanin) carrier protein, then screened in an immunoassay for Chagasic antibody recognition.  The best recognized saccharides were used to immunize alpha-1,3-Gal-T-KO mice, which showed prolonged survival following a lethal dose of T. Cruzi compared to control groups.  This led to synthesis of a glycolipopeptide composed of a B-cell epitope (alpha-galactosides), a T-cell epitope, and a lipid residue needed for an efficient uptake by antigen presenting cells.

<i>Trypanosoma cruzi</i>-derived sugar epitopes: Synthesis and Immunology

243rd National Meeting (2012)

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Trypanosoma cruzi-derived sugar epitopes: Synthesis and Immunology