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首页> 外文期刊>Chemistry: A European journal >Improved synthesis and mutagenicity of oligonucleotides containing 5-hydroxymethylcytosine, 5-formylcytosine and 5-carboxylcytosine
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Improved synthesis and mutagenicity of oligonucleotides containing 5-hydroxymethylcytosine, 5-formylcytosine and 5-carboxylcytosine

机译：改进了含有5-羟甲基胞嘧啶，5-甲酰基胞嘧啶和5-羧甲基胞嘧啶的寡核苷酸的合成和诱变性

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摘要

5-Formylcytosine (fC or ~(5-CHO)dC) and 5-carboxylcytosine (caC or ~(5-COOH)dC) have recently been identified as constituents of mammalian DNA. The nucleosides are formed from 5-methylcytosine (mC or ~(5-Me)dC) via 5-hydroxymethylcytosine (hmC or ~(5-HOMe)dC) and are possible intermediates of an active DNA demethylation process. Here we show efficient syntheses of phosphoramidites which enable the synthesis of DNA strands containing these cytosine modifications based on Pd~0-catalyzed functionalization of 5-iododeoxycytidine. The first crystal structure of fC reveals the existence of an intramolecular H-bond between the exocyclic amine and the formyl group, which controls the conformation of the formyl substituent. Using a newly designed in vitro mutagenicity assay we show that fC and caC are only marginally mutagenic, which is a prerequisite for the bases to function as epigenetic control units.
机译：最近已鉴定出5-甲酰基胞嘧啶（fC或〜（5-CHO）dC）和5-羧基胞嘧啶（caC或〜（5-COOH）dC）是哺乳动物DNA的组成部分。核苷由5-甲基胞嘧啶（mC或〜（5-Me）dC）经由5-羟甲基胞嘧啶（hmC或〜（5-HOMe）dC）形成，并且可能是活性DNA脱甲基过程的中间体。在这里，我们显示了亚磷酰胺的有效合成，其能够基于Pd〜0催化的5-碘脱氧胞苷的功能化合成包含这些胞嘧啶修饰的DNA链。 fC的第一个晶体结构表明在环外胺和甲酰基之间存在分子内H键，该键控制甲酰基取代基的构象。使用新设计的体外诱变试验，我们显示fC和caC只是轻微诱变，这是碱基充当表观遗传控制单位的前提。

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