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

ABSTRACT: 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.

SUBMITTER: Kaiser MM

PROVIDER: S-EPMC7111817 | biostudies-literature | 2012 May

REPOSITORIES: biostudies-literature

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

Kaiser Martin Maxmilian MM Jansa Petr P Dračínský Martin M Janeba Zlatko Z

Tetrahedron 20120326 21

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 ...[more]

PMID: 32287422

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