One-pot synthesis of nucleoside 5'-triphosphates from nucleoside 5'-H-phosphonates.
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.
Sun
Qi
Q
Department of Chemistry, The Pennsylvania State University, University Park, PA 16802, USA.
Edathil
Jocelyn P
JP
Wu
Runzhi
R
Smidansky
Eric D
ED
Cameron
Craig E
CE
Peterson
Blake R
BR
D009705:Nucleosides / Q000737:chemistry*; D009711:Nucleotides / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D063065:Organophosphonates / Q000737:chemistry*; D017955:Poliovirus / Q000201:enzymology; D012324:RNA-Dependent RNA Polymerase / Q000378:metabolism
D009705:Nucleosides; D009711:Nucleotides; D063065:Organophosphonates; D012324:RNA-Dependent RNA Polymerase