Synthesis of a phostone glycomimetic of the endothelin converting enzyme inhibitor phosphoramidon

The phostone analog of phosphoramidon, an inhibitor of endothelin converting enzyme, was synthesized from -rhamnose. Coupling of the cyclic phosphonic acid with the dipeptide H-Leu-Trp-OMe gave, after deprotection and purification by reverse-phase HPLC, the desired phostone which exhibited an IC50 of 5.05 ± 2.7 μM.