Phosphomimetic sulfonamide and sulfonamidoxy analogues of (Lyso)phosphatidic acid

Lysophosphatidic acid (LPA) and phosphatidic acid (PA) are potent bioactive lipid mediators of signal transduction and are inactivated by phosphatases. To obtain receptor-isoform selective ligands with neutral phosphomimetic head groups, we performed the stereoselective synthesis of LPA and PA analogues with trifluoromethanesulfonamide and trifluoromethanesulfonamidoxy moieties replacing the phosphomonoester.