从核苷5'-H-膦酸酯一锅法合成核苷5'-三磷酸酯。
One-pot synthesis of nucleoside 5'-triphosphates from nucleoside 5'-H-phosphonates.
作者信息
Sun Qi, Edathil Jocelyn P, Wu Runzhi, Smidansky Eric D, Cameron Craig E, Peterson Blake R
机构信息
Department of Chemistry, The Pennsylvania State University, University Park, PA 16802, USA.
出版信息
Org Lett. 2008 May 1;10(9):1703-6. doi: 10.1021/ol8003029. Epub 2008 Apr 8.
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.
摘要
核苷5'-三磷酸（NTPs）在生物学和医学中发挥着关键作用。然而，这些化合物极难合成。我们描述了一种通过吡啶鎓氨基磷酸酯从核苷5'-H-膦酸单酯制备NTPs的一锅法，并且我们使用这种方法合成了ATP、UTP、GTP、CTP、利巴韦林-TP和6-甲基嘌呤核糖核苷-TP（6MePTP）。脊髓灰质炎病毒RNA依赖性RNA聚合酶有效地将6MePTP用作底物，这表明同源核苷（一种了解甚少的抗病毒剂）可能会破坏病毒RNA。
相似文献
1
One-pot synthesis of nucleoside 5'-triphosphates from nucleoside 5'-H-phosphonates.
Org Lett. 2008 May 1;10(9):1703-6. doi: 10.1021/ol8003029. Epub 2008 Apr 8.
2
Ethynyl, 2-Propynyl, and 3-Butynyl C-Phosphonate Analogues of Nucleoside Di- and Triphosphates: Synthesis and Reactivity in CuAAC.
Org Lett. 2015 Jun 19;17(12):3062-5. doi: 10.1021/acs.orglett.5b01346. Epub 2015 May 29.
3
Aryl nucleoside H-phosphonates as a tool for investigation of stereospecificity during coupling.
Nucleosides Nucleotides Nucleic Acids. 2005;24(5-7):887-90. doi: 10.1081/ncn-200059239.
4
Nucleoside 3',5'-cyclic H-phosphonates, new useful precursors for the synthesis of nucleoside 3',5'-cyclic phosphates and their analogues.
Org Lett. 2013 Aug 16;15(16):4082-5. doi: 10.1021/ol4016404. Epub 2013 Aug 1.
5
Aryl h-phosphonates. 14. Synthesis of new nucleotide analogues with phosphonate-phosphate internucleosidic linkage.
Org Lett. 2003 Oct 2;5(20):3571-3. doi: 10.1021/ol035166u.
6
Synthesis of Nucleoside Triphosphates from 2'-3'-Protected Nucleosides Using Trimetaphosphate.
Org Lett. 2016 Feb 5;18(3):580-3. doi: 10.1021/acs.orglett.5b03624. Epub 2016 Jan 13.
7
Synthesis of α-L-threose nucleoside phosphonates via regioselective sugar protection.
J Org Chem. 2013 Jul 19;78(14):7137-44. doi: 10.1021/jo400907g. Epub 2013 Jul 3.
8
Convenient synthesis of nucleoside 5'-triphosphates for RNA transcription.
Chem Commun (Camb). 2011 Jul 28;47(28):8142-4. doi: 10.1039/c1cc12201k. Epub 2011 Jun 14.
9
Thermal synthesis of nucleoside H-phosphonates under mild conditions.
Orig Life Evol Biosph. 2005 Feb;35(1):1-10. doi: 10.1007/s11084-005-0093-9.
10
Scalable Multistep One-Pot Synthesis of Natural and Modified Nucleoside Triphosphates.
J Org Chem. 2025 May 2;90(17):5936-5948. doi: 10.1021/acs.joc.5c00268. Epub 2025 Apr 23.
引用本文的文献
1
The First 5'-Phosphorylated 1,2,3-Triazolyl Nucleoside Analogues with Uracil and Quinazoline-2,4-Dione Moieties: A Synthesis and Antiviral Evaluation.
Molecules. 2022 Sep 21;27(19):6214. doi: 10.3390/molecules27196214.
2
A Chemical Strategy for Intracellular Arming of an Endogenous Broad-Spectrum Antiviral Nucleotide.
J Med Chem. 2021 Oct 28;64(20):15429-15439. doi: 10.1021/acs.jmedchem.1c01481. Epub 2021 Oct 18.
3
Synthesis of 4-Cyanoindole Nucleosides, 4-Cyanoindole-2'-Deoxyribonucleoside-5'-Triphosphate (4CIN-TP), and Enzymatic Incorporation of 4CIN-TP into DNA.
Curr Protoc Nucleic Acid Chem. 2020 Mar;80(1):e101. doi: 10.1002/cpnc.101.
4
Synthetic Strategies for Dinucleotides Synthesis.
Molecules. 2019 Nov 27;24(23):4334. doi: 10.3390/molecules24234334.
5
Pyrophosphorylation selective phosphoprotein derivatization.
Chem Sci. 2018 Jun 12;9(27):5929-5936. doi: 10.1039/c8sc01233d. eCollection 2018 Jul 21.
6
Nucleoside triphosphates--building blocks for the modification of nucleic acids.
Molecules. 2012 Nov 15;17(11):13569-91. doi: 10.3390/molecules171113569.
7
The synthesis of 2'-methylseleno adenosine and guanosine 5'-triphosphates.
Bioorg Med Chem. 2012 Apr 1;20(7):2416-8. doi: 10.1016/j.bmc.2012.01.044. Epub 2012 Feb 4.
8
Protection-free one-pot synthesis of 2'-deoxynucleoside 5'-triphosphates and DNA polymerization.
Org Lett. 2011 Aug 19;13(16):4156-9. doi: 10.1021/ol201073e. Epub 2011 Jul 26.
9
Synthesis of a 6-methyl-7-deaza analogue of adenosine that potently inhibits replication of polio and dengue viruses.
J Med Chem. 2010 Nov 25;53(22):7958-66. doi: 10.1021/jm100593s. Epub 2010 Oct 22.
本文引用的文献
1
Lethal mutagenesis of picornaviruses with N-6-modified purine nucleoside analogues.
Antimicrob Agents Chemother. 2008 Mar;52(3):971-9. doi: 10.1128/AAC.01056-07. Epub 2008 Jan 7.
2
Synthesis of a universal 5-nitroindole ribonucleotide and incorporation into RNA by a viral RNA-dependent RNA polymerase.
Chembiochem. 2007 Aug 13;8(12):1359-62. doi: 10.1002/cbic.200700160.
3
Selective diphosphorylation, dithiodiphosphorylation, triphosphorylation, and trithiotriphosphorylation of unprotected carbohydrates and nucleosides.
Org Lett. 2005 Dec 8;7(25):5589-92. doi: 10.1021/ol0521432.
4
Synthesis and biological activity of 2-fluoro adenine and 6-methyl purine nucleoside analogs as prodrugs for suicide gene therapy of cancer.
Nucleosides Nucleotides Nucleic Acids. 2005;24(5-7):881-5. doi: 10.1081/ncn-200059237.
5
A novel method for the preparation of nucleoside triphosphates from activated nucleoside phosphoramidates.
Org Lett. 2004 Jun 24;6(13):2257-60. doi: 10.1021/ol049267j.
6
A combination chemical and enzymatic approach for the preparation of azole carboxamide nucleoside triphosphate.
J Org Chem. 2003 May 16;68(10):3860-5. doi: 10.1021/jo020745i.
7
[Anhydride and halogenated-anhydride trihalogenacetic acid interaction with thymidine-5'-phosphate: ways to new activating reagents in nucleotide phosphorylation reactions].
Bioorg Khim. 2003 Jan-Feb;29(1):64-74. doi: 10.1023/a:1022282503476.
8
One-pot synthesis of hydrogen phosphonate derivatives of d4T and AZT.
Chem Commun (Camb). 2002 Oct 21(20):2414-5. doi: 10.1039/b207657h.
9
Synthesis and antiviral evaluation of a mutagenic and non-hydrogen bonding ribonucleoside analogue: 1-beta-D-Ribofuranosyl-3-nitropyrrole.
Biochemistry. 2002 Jul 23;41(29):9026-33. doi: 10.1021/bi026120w.
10
Syntheses of nucleoside triphosphates.
Chem Rev. 2000 Jun 14;100(6):2047-60. doi: 10.1021/cr990045m.
Zotero 插件