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

doi:10.1021/ol8003029

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 journal › Article › peer-review

43 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 language	English (US)
Pages (from-to)	1703-1706
Number of pages	4
Journal	Organic Letters
Volume	10
Issue number	9
DOIs	https://doi.org/10.1021/ol8003029
State	Published - May 1 2008

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol8003029

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title = "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.",

author = "Qi Sun and Edathil, \{Jocelyn P.\} and Runzhi Wu and Smidansky, \{Eric D.\} and Cameron, \{Craig E.\} and Peterson, \{Blake R.\}",

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T1 - One-pot synthesis of nucleoside 5 -triphosphates from nucleoside 5 -H-phosphonates

AU - Sun, Qi

AU - Edathil, Jocelyn P.

AU - Wu, Runzhi

AU - Smidansky, Eric D.

AU - Cameron, Craig E.

AU - Peterson, Blake R.

PY - 2008/5/1

Y1 - 2008/5/1

N2 - 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.

AB - 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.

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AN - SCOPUS:48849091987

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JO - Organic Letters

JF - Organic Letters

IS - 9

ER -

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

Abstract

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