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One-pot synthesis of nucleoside 5'-triphosphates from nucleoside 5'-H-phosphonates.

ABSTRACT: Nucleoside 5'-triphosphates (NTPs) play key roles in biology and medicine. However, these compounds are notoriously difficult to synthesize. We describe a one-pot method to prepare NTPs from nucleoside 5'-H-phosphonate monoesters via pyridinium phosphoramidates, and we used this approach to synthesize ATP, UTP, GTP, CTP, ribavirin-TP, and 6-methylpurine ribonucleoside-TP (6MePTP). Poliovirus RNA-dependent RNA polymerase efficiently employed 6MePTP as a substrate, suggesting that the cognate nucleoside, a poorly understood antiviral agent, may damage viral RNA.

SUBMITTER: Sun Q

PROVIDER: S-EPMC3104733 | biostudies-literature | 2008 May

REPOSITORIES: biostudies-literature

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One-pot synthesis of nucleoside 5'-triphosphates from nucleoside 5'-H-phosphonates.

Sun Qi Q Edathil Jocelyn P JP Wu Runzhi R Smidansky Eric D ED Cameron Craig E CE Peterson Blake R BR

Organic letters 20080408 9

Nucleoside 5'-triphosphates (NTPs) play key roles in biology and medicine. However, these compounds are notoriously difficult to synthesize. We describe a one-pot method to prepare NTPs from nucleoside 5'-H-phosphonate monoesters via pyridinium phosphoramidates, and we used this approach to synthesize ATP, UTP, GTP, CTP, ribavirin-TP, and 6-methylpurine ribonucleoside-TP (6MePTP). Poliovirus RNA-dependent RNA polymerase efficiently employed 6MePTP as a substrate, suggesting that the cognate nucl ...[more]

PMID: 18393512

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