Post-synthetic transamination at position N4 of cytosine in oligonucleotides assembled with routinely used phosphoramidites,Organic & Biomolecular Chemistry

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Post-synthetic transamination at position N4 of cytosine in oligonucleotides assembled with routinely used phosphoramidites
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2020-11-06 , DOI: 10.1039/d0ob02059a
Rémy Lartia ₁ , Coelio Vallée , Eric Defrancq

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The commercially available and cheap nucleotide phosphoramidites are routinely used for the oligonucleotide (ODN) assembly. T, isobutyryl-dG (^iBudG), benzoyl-dA (^BzdA), acetyl-dC (^AcdC) and benzoyl-dC (^BzdC) derivatives are sufficient to produce orthogonally protected ODNs. Clean and efficient (ca. 30%–70% yield) post-synthetic amination of an ODN assembled with such phosphoramidites was selectively achieved at the N4 position of a singly introduced ^BzdC. Such a method represents a novel and cheap strategy for the user-friendly post-modification of oligonucleotides at the internal position.

中文翻译：

用常规使用的亚磷酰胺组装的寡核苷酸中胞嘧啶 N4 位的合成后转氨

市售且廉价的核苷酸亚磷酰胺通常用于寡核苷酸（ODN）组装。 T、异丁酰-dG ( ^iBu dG)、苯甲酰-dA ( ^Bz dA)、乙酰基-dC ( ^Ac dC) 和苯甲酰-dC ( ^Bz dC) 衍生物足以产生正交保护的 ODN。在单独引入的^Bz dC 的 N4 位置选择性地实现了与此类亚磷酰胺组装的 ODN 的清洁高效（产率约30%–70%）的合成后胺化。这种方法代表了一种新颖且廉价的策略，用于在内部位置对寡核苷酸进行用户友好的后修饰。

更新日期：2020-11-19

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