Towards the synthesis of (2S,3S,E)-ceramide-1,3-phosphodiester; Phosphosphingolipid analogs as potential modulators of the enzymatic activity

Abstract

The study of new biologically active molecules for the understanding of the cellular functioning is essential for the advancement of modern medicine. This project is focused on the synthesis of the (2S,3S,E)-ceramide-1,3-phosphodiester, a synthetic molecule inspired by three molecules with a determinant role in the life cycle of animal cells: ceramide, ceramide-1-phosphate and the corresponding cyclic phosphate. Slight changes into the structures of the mentioned molecules may change, and even invert their cellular role. Therefore, and considering that the biological function is very dependent on the structural changes, it has been decided to carry out the insertion of a cyclic phosphodiester into the ceramide backbone, as well as the change to a non-natural (2S,3S) configuration instead of the natural (2S,3R), while maintaining the E configuration of the double bond