The Chemical Synthesis of Bioactive Glycosylphosphatidylinositols from Trypanosoma cruzi Containing an Unsaturated Fatty Acid in the Lipid

摘要

Glycosylphosphatidylinositols (GPIs) are a class of natural glycosylphospholipids that anchor proteins and glycoproteins (through their C terminus) as well as phosphoglycans (through the reducing end of the chain) to the membrane of eukaryotic cells. Since the first full assignment of a GPI structure in 1988,[1] a number of GPI anchors have been characterized.[2] The function of the compounds, in addition to the clear one of linking the above biopolymers to membranes, has been extensively discussed.[2], [3] There is also evidence that GPIs and/or their metabolites can act as secondary messengers, which modulate biological events including insulin production, insulin-mediated signal transduction, cellular proliferation, and cell-cell recognition. The discovered role as mediators of regulatory processes makes the chemical preparation of the compounds and their analogues of great interest. To date, a number of syntheses of GPIs (yeast,[4] rat brain Thy-1,[5] Trypanosoma brucei,[6] Leishmania,[7] T. gondii,[8] Plasmodium falciparum,[9] and T. cruzi 1G7 antigen[10]) have been reported.