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

Qi Sun, Jocelyn P. Edathil, Runzhi Wu, Eric D. Smidansky, Craig E. Cameron, Blake R. Peterson

Research output: Contribution to journalArticlepeer-review

37 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)1703-1706
Number of pages4
JournalOrganic Letters
Volume10
Issue number9
DOIs
StatePublished - May 1 2008

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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