Efficient Synthesis of Trifluoromethylated Purine Ribonucleosides and Ribonucleotides

Q4 Chemistry

Current Protocols in Nucleic Acid Chemistry Pub Date : 2020-09-29 DOI:10.1002/cpnc.118

Mikolaj Chrominski, Joanna Kowalska, Jacek Jemielity

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引用次数: 1

Abstract

The protocols presented in this article describe highly detailed synthesis of trifluoromethylated purine nucleotides and nucleosides (G and A). The procedure involves trifluoromethylation of properly protected (acetylated) nucleosides, followed by deprotection leading to key CF₃-containing nucleosides. This gives synthetic access to 8-CF₃-substituted guanosine derivatives and three adenosine derivatives (8-CF₃, 2-CF₃, and 2,8-diCF₃). In further steps, phosphorylation and phosphate elongation (for selected examples) result in respective trifluoromethylated nucleoside mono-, di-, and triphosphates. Support protocols are included for compound handling, purification procedures, analytical sample preparation, and analytical techniques used throughout the performance of the basic protocols. © 2020 Wiley Periodicals LLC.

Basic Protocol 1: Synthesis of trifluoromethylated guanosine and adenosine derivatives

Basic Protocol 2: Synthesis of trifluoromethylated guanosine and adenosine monophosphates

Basic Protocol 3: Synthesis of phosphorimidazolides of ^8-CF3GMP and ^8-CF3AMP

Basic Protocol 4: Synthesis of trifluoromethylated guanosine and adenosine oligophosphates

Support Protocol 1: TLC sample preparation and analysis

Support Protocol 2: Purification protocol for Basic Protocol 1

Support Protocol 3: HPLC analysis and preparative HPLC

Support Protocol 4: Ion-exchange chromatography

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三氟甲基化嘌呤核糖核苷和核糖核苷酸的高效合成

本文中介绍的方案非常详细地描述了三氟甲基化嘌呤核苷酸和核苷(G和A)的合成。该过程包括适当保护(乙酰化)核苷的三氟甲基化，然后去保护导致关键的含cf3核苷。这样就可以合成8-CF3取代的鸟苷衍生物和三种腺苷衍生物(8-CF3、2- cf3和2,8- dicf3)。在进一步的步骤中，磷酸化和磷酸延伸(对于选定的例子)分别产生三氟甲基化核苷单磷酸、二磷酸和三磷酸。支持方案包括化合物处理，纯化程序，分析样品制备，以及在基本方案执行过程中使用的分析技术。©2020 Wiley期刊有限公司基本方案1:三氟甲基化鸟苷和腺苷衍生物的合成基本方案2:三氟甲基化鸟苷和腺苷单磷酸的合成基本方案3:8-CF3GMP和8- cf3ampp的磷咪唑类化合物的合成基本方案4:三氟甲基化鸟苷和腺苷寡磷酸的合成支持方案1:TLC样品制备和分析支持方案2:支持方案3:高效液相色谱分析和制备支持方案4:离子交换色谱

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Current Protocols in Nucleic Acid Chemistry Chemistry-Organic Chemistry

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期刊介绍： Published in association with International Society for Nucleosides, Nucleotides & Nucleic Acids (IS3NA) , Current Protocols in Nucleic Acid Chemistry is equally valuable for biotech, pharmaceutical, and academic labs. It is the resource for designing and running successful research projects in the rapidly growing and changing field of nucleic acid, nucleotide, and nucleoside research.