Amine‐to‐Azide Conversion on Native RNA via Metal‐Free Diazotransfer Opens New Avenues for RNA Manipulations,Angewandte Chemie International Edition

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Amine‐to‐Azide Conversion on Native RNA via Metal‐Free Diazotransfer Opens New Avenues for RNA Manipulations
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2021-01-05 , DOI: 10.1002/anie.202015034
Olga A Krasheninina ₁ , Julia Thaler ₁ , Matthias D Erlacher ₂ , Ronald Micura ₁

Affiliation

A major challenge in the field of RNA chemistry is the identification of selective and quantitative conversion reactions on RNA that can be used for tagging and any other RNA tool development. Here, we introduce metal‐free diazotransfer on native RNA containing an aliphatic primary amino group using the diazotizing reagent fluorosulfuryl azide (FSO₂N₃). The reaction provides the corresponding azide‐modified RNA in nearly quantitatively yields without affecting the nucleobase amino groups. The obtained azido‐RNA can then be further processed utilizing well‐established bioortho‐gonal reactions, such as azide‐alkyne cycloadditions (Click) or Staudinger ligations. We exemplify the robustness of this approach for the synthesis of peptidyl‐tRNA mimics and for the pull‐down of 3‐(3‐amino‐3‐carboxypropyl)uridine (acp³U)‐ and lysidine (k²C)‐containing tRNAs of an Escherichia coli tRNA pool isolated from cellular extracts. Our approach therefore adds a new dimension to the targeted chemical manipulation of diverse RNA species.

中文翻译：

通过无金属重氮转移将天然 RNA 转化为胺至叠氮化物，为 RNA 操作开辟了新途径

RNA 化学领域的一个主要挑战是识别 RNA 上的选择性和定量转化反应，可用于标记和任何其他 RNA 工具的开发。_{在这里，我们使用重氮化试剂氟磺酰叠氮 (FSO 2} N ₃ )在含有脂肪族伯氨基的天然 RNA 上引入无金属重氮转移。该反应以几乎定量的产率提供了相应的叠氮化物修饰的 RNA，且不影响核碱基氨基。然后可以利用成熟的生物正交反应进一步处理获得的叠氮基-RNA，例如叠氮-炔环加成（Click）或施陶丁格连接。我们举例说明了这种方法对于合成肽基-tRNA模拟物以及下拉包含3-(3-氨基-3-羧丙基)尿苷(acp ³ U)和赖氨酸(k ² C)的tRNA的稳健性从细胞提取物中分离出的大肠杆菌 tRNA 池。因此，我们的方法为不同 RNA 物种的靶向化学操作增加了一个新的维度。

更新日期：2021-01-05

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