Synthesis and Functionality Study of Photoswitchable Hydrazone Oligodeoxynucleotides
Synthesis and Functionality Study of Photoswitchable Hydrazone Oligodeoxynucleotides
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DOI：
10.1002/cpz1.295
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发表时间：
2021-11
期刊：
影响因子：
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通讯作者：
Z. Chang;S. Mao;Y. Zheng;J. Sheng
中科院分区：
文献类型：
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作者：
Z. Chang;S. Mao;Y. Zheng;J. Sheng
本文提供了一种化学合成和表征可光开关的硫代亚磷酰胺并将其掺入到寡核苷酸中的详细方法。该合成开始于商业上可获得的脱氧尿苷，然后在没有碱的情况下，通过阿佩尔反应将4-氧代转化为4-氯部分，以安装关键的肼基团。硫代亚磷酰胺构筑块与用于固相合成寡聚脱氧核苷酸的传统酰胺化学方案兼容。我们的方法通过添加一种新颖的、功能强大的DNA构建块来扩展当前的核苷酸池，该构建块适合广泛的应用，包括调节DNA-酶的相互作用和通过细胞友好的蓝光照射来合成DNA。©2021威利期刊有限责任公司。
This article provides a detailed procedure for the chemical synthesis and characterization of photoswitchable hydrazone phosphoramidite and its incorporation into oligodeoxynucleotides. The synthesis starts with commercially available deoxyuridine, followed by conversion of the 4‐oxo into a 4‐chloro moiety via Appel reaction to install the key hydrazone group in the absence of base. The hydrazone phosphoramidite building block is compatible with the conventional amidite chemistry protocols for solid‐phase synthesis of oligodeoxynucleotides. Our method expands the current nucleotide pool by adding a novel, functional DNA building block that is suitable for a broad spectrum of applications, including the regulation of DNA‐enzyme interactions and DNA synthesis by irradiation with cell‐friendly blue light. © 2021 Wiley Periodicals LLC.