Butylacrylate-nucleobase Conjugates as Targets for Two-step Redox Labeling of DNA with an Osmium Tetroxide Complex,Electroanalysis

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Butylacrylate-nucleobase Conjugates as Targets for Two-step Redox Labeling of DNA with an Osmium Tetroxide Complex
Electroanalysis ( IF 2.7 ) Pub Date : 2017-12-27 , DOI: 10.1002/elan.201700702
Pavlína Havranová-Vidláková ₁ , Jan Špaček ₁ , Lada Vítová ₁ , Monika Hermanová ₁ , Jitka Dadová ₂ , Veronika Raindlová ₂ , Michal Hocek _{2,

3} , Miroslav Fojta _{1,

4} , Luděk Havran ₁

Affiliation

Modification of nucleic acids with osmium tetroxide reagents (Os,L, such as OsO4,2,2-bipyridine, Os,bpy) has been applied in redox DNA labeling, in probing DNA structure as well as in studies of DNA interactions with other molecules. In natural DNA, primarily thymine residues form adducts with the Os,bpy in a structure selective manner. In this paper we introduce a new two-step technique of DNA modification with the electroactive Os,bpy, consisting in enzymatic construction of DNA bearing butyl acrylate (BA) moieties attached to uracil at C5 or to 7-deaza adenine at C7, followed by chemical modification of a reactive C=C double bond in the acrylate residue. We demonstrate a facile modification of the BA conjugates in both single- and double-stranded (ds) DNA under conditions when modification within the nucleobase rings in ds DNA is hindered. Various DNA-Os,bpy adducts can easily be analyzed electrochemically and distinguished by different redox potentials. The two-step procedure appears to be applicable in osmium redox labelling of ds DNA.

中文翻译：

丙烯酸丁酯-核碱基共轭物作为四氧化锇复合物两步氧化还原标记 DNA 的靶标

用四氧化锇试剂（Os,L，例如 OsO4,2,2-bipyridine, Os,bpy）修饰核酸已应用于氧化还原 DNA 标记、探测 DNA 结构以及研究 DNA 与其他分子的相互作用. 在天然 DNA 中，主要是胸腺嘧啶残基以结构选择性方式与 Os,bpy 形成加合物。在本文中，我们介绍了一种使用电活性 Os,bpy 进行 DNA 修饰的新两步技术，包括酶促构建带有丙烯酸丁酯 (BA) 部分的 DNA，该部分连接到 C5 的尿嘧啶或连接到 C7 的 7-脱氮腺嘌呤，然后是丙烯酸酯残基中反应性 C=C 双键的化学改性。我们证明了在 ds DNA 中的核碱基环内的修饰受到阻碍的条件下，可以轻松修饰单链和双链 (ds) DNA 中的 BA 缀合物。各种 DNA-Os、bpy 加合物可以很容易地进行电化学分析，并通过不同的氧化还原电位进行区分。两步程序似乎适用于 ds DNA 的锇氧化还原标记。

更新日期：2017-12-27

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