The Chemical Synthesis of Glycosylphosphatidylinositol Anchors from Trypanosoma Cruzi Trypomastigote Mucins — Exploration of Ester‐ and Acetal‐Type Permanent Protecting Groups

The protozoan parasite Trypanosoma cruzi is a causative agent of Chagas' disease, which affects millions of people in South and Central America. Throughout the life cycle, T. cruzi produce both common and stage-specific glycosylphosphatidylinositol(GPI)-anchored cell-surface macromolecules. The purified GPI fraction of T. cruzi trypomastigote mucins (tGPI) revealed extraordinary pro-inflammatory activity (comparable to those of bacterial lipopolysaccharide), which was allegedly associated with the presence of unsaturated fatty acids in the lipid moiety (structures 1 and 2). Two distinct novel synthetic strategies, both implicating the use of non-benzyl type protecting groups, were designed and applied for the chemical preparation of the tGPIs 1 and 2.