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首页> 外文期刊>Current Protocols in Nucleic Acid Chemistry >Solid-Phase Synthesis of RNA 5'-Azides and Their Application for Labeling, Ligation, and Cyclization Via Click Chemistry
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Solid-Phase Synthesis of RNA 5'-Azides and Their Application for Labeling, Ligation, and Cyclization Via Click Chemistry

机译：固相合成的RNA 5 ' -Azides和他们申请标签、结扎通过点击化学环化

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摘要

RNAs with 5; functional groups have been gaining interest as molecular probes and reporter molecules. Copper-catalyzed azide-alkyne cycloaddition is one of the most straightforward methods to access such molecules; however, RNA functionalization withazide group has been posing a synthetic challenge. This article describes a simple and efficient protocol for azide functionalization of oligoribonucleotides 5'-end in solid-phase. An azide moiety is attached directly to the C5'-end in two steps: (i) -OHto -I conversion using methyltriph-enoxyphosphonium iodide, and (ii) -I to -N3 substitution using sodium azide. The reactivity of the resulting compounds is exemplified by fluorescent labeling using both copper(I)-catalyzed (CuAAC) and strain-promoted (SPAAC) azide-alkyne cycloaddition reactions, ligation of two RNA fragments, and cyclization of short bifunctionalized oligonucleotides. The protocol makes use of oligori-bonucleotides synthesized by standard phosphoramidite approach on solid support, using commercially available 2;-0-PivOM-protected monomers. Such a protection strategy eliminates the interference between the iodination reagent and silyl protecting groups (TBDMS, TOM) commonly used in RNA synthesis by phosphoramidite approach.
机译：rna 5;兴趣作为分子探针和记者分子。环加成反应是一种最简单方法访问这些分子;功能化withazide集团已摆姿势一个合成的挑战。叠氮化的简单和有效的协议功能化oligoribonucleotides 5 '端在固相。直接C5 '在两个步骤:(i) -OHto我转换使用methyltriph-enoxyphosphonium碘化,(2)- n3替换使用叠氮化钠。以荧光标记化合物使用铜(I)催化(CuAAC)和strain-promoted azide-alkyne (SPAAC)两个RNA的环加成反应,结扎片段,和短的环化bifunctionalized寡核苷酸。利用oligori-bonucleotides合成标准phosphoramidite方法在固体支持,使用商用2, 0-pivom-protected单体。策略之间的干扰消除碘化试剂和甲硅烷基保护组(汤姆TBDMS)常用的RNA合成的phosphoramidite方法。

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