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Changed reactivity of secondary hydroxy groups in C8-modified adenosine – lessons learned from silylation
Beilstein Journal of Organic Chemistry ( IF 2.7 ) Pub Date : 2020-11-23 , DOI: 10.3762/bjoc.16.234
Jennifer Frommer , Sabine Müller

Synthesis of site-specifically modified oligonucleotides has become a major tool for RNA structure and function studies. Reporter groups or specific functional entities are required to be attached at a pre-defined site of the oligomer. An attractive strategy is the incorporation of suitably functionalized building blocks that allow post-synthetic conjugation of the desired moiety. A C8-alkynyl-modified adenosine derivative was synthesized, reviving an old synthetic pathway for iodination of purine nucleobases. Silylation of the C8-alkynyl-modified adenosine revealed unexpected selectivity of the two secondary sugar hydroxy groups, with the 3'-O-isomer being preferentially formed. Optimization of the protection scheme lead to a new and economic route to the desired C8-alkynylated building block and its incorporation in RNA.

中文翻译:

C8修饰的腺苷中仲羟基反应性的变化–甲硅烷基化的经验教训

特定位点修饰的寡核苷酸的合成已成为RNA结构和功能研究的主要工具。报告者基团或特定的功能实体必须连接在低聚物的预定位点。一种有吸引力的策略是掺入适当功能化的结构单元,以允许所需部分的合成后缀合。合成了C8-炔基修饰的腺苷衍生物,从而恢复了嘌呤核碱基碘化的古老合成途径。C8-炔基修饰的腺苷的甲硅烷基化显示两个仲糖羟基具有3'- O的出乎意料的选择性-优先形成的异构体。保护方案的优化导致了一条新的经济途径,可通往所需的C8-炔基化构件并将其并入RNA。
更新日期:2020-11-23
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