Monatshefte für Chemie - Chemical Monthly ( IF 1.7 ) Pub Date : 2022-02-22 , DOI: 10.1007/s00706-022-02896-x Sarah Moreno 1 , Laurin Flemmich 1 , Ronald Micura 1
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The growing interest in 3-methylcytidine (m3C) originates from the recent discoveries of m3C modified tRNAs in humans as well as its intensively debated occurrence in mRNA. Moreover, m3C formation can be catalyzed by RNA without the assistance of proteins as has been demonstrated for a naturally occurring riboswitch fold using the methylated form of its cognate ligand as cofactor. Additionally, new RNA sequencing methods have been developed to detect this modification in transcriptome-wide manner. For all these reasons, an increasing demand for synthetic m3C containing oligoribonucleotides is emerging. Their chemical synthesis relies on RNA solid-phase synthesis using phosphoramidite building blocks. Here, we describe a facile synthetic path towards N4-acetylated 2′-O-TBDMS- and 2′-O-TOM m3C phosphoramidites to provide an optimal toolbox for solid-phase synthesis of m3C containing RNA.
Graphical abstract
中文翻译：
用于 RNA 固相合成的 N4-乙酰化 3-甲基胞苷亚磷酰胺的合成
对 3-甲基胞苷 (m 3 C)日益增长的兴趣源于最近在人类中发现的 m 3 C 修饰的 tRNA 以及它在 mRNA 中的激烈争论。此外，m 3 C 的形成可以由 RNA 催化而无需蛋白质的帮助，正如使用其同源配体的甲基化形式作为辅因子的天然发生的核糖开关折叠所证明的那样。此外，已经开发出新的 RNA 测序方法以在转录组范围内检测这种修饰。由于所有这些原因，对合成 m 3的需求不断增加含有 C 的寡核糖核苷酸正在出现。它们的化学合成依赖于使用亚磷酰胺构建块的 RNA 固相合成。在这里，我们描述了一条通往 N 4 -乙酰化 2' - O -TBDMS- 和 2' - O -TOM m 3 C 亚磷酰胺的简便合成途径，为含 m 3 C 的 RNA的固相合成提供了最佳工具箱。
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