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/NaClO2/NaClO oxidizing system. Although (S)-3-(adenin-9-yl)-2-(phosphonomethoxy)propanoic acid ((S)-CPMEA) has been designed as a compound with potential anti-HIV activity, none of the newly prepared CPME analogues exhibited any antiviral activity.

Institute of Organic Chemistry and Biochemistry Academy of Sciences of the Czech Republic v v i Flemingovo nám 2 CZ 16610 Prague 6 Czech Republic

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ArgusLab 4.0, M. A. Thompson, Planaria Software LLC, Seattle, http://www.ArgusLab.com.

Regioselective Palmitoylation of 9-(2,3-Dihydroxy- propyl)adenine Catalyzed by a Glycopolymer-enzyme Conjugate