A novel type of acyclic nucleoside phosphonates derived from 2-(phosphonomethoxy)propanoic acid.

A convenient and efficient synthesis of a novel class of acyclic nucleoside phosphonates derived from 2-(phosphonomethoxy)propanoic acid has been developed. The key step of the synthesis is the optimized oxidation of the 3-hydroxy-2-(phosphonomethoxy)propyl (HPMP) analogues to the corresponding 2'-carboxy-PME (CPME) derivatives using the TEMPO/NaClO/NaClO oxidizing system. Although ()-3-(adenin-9-yl)-2-(phosphonomethoxy)propanoic acid (()-CPMEA) has been designed as a compound with potential anti-HIV activity, none of the newly prepared CPME analogues exhibited any antiviral activity.