DNA Functionality with Photoswitchable Hydrazone Cytidine**
DNA Functionality with Photoswitchable Hydrazone Cytidine**
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具有光开关腙胞苷的 DNA 功能**
DOI：
10.1002/chem.202100742
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发表时间：
2021
期刊：
影响因子：
--
通讯作者：
Sheng, Jia
中科院分区：
文献类型：
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作者：
Mao, Song;Chang, Zhihua;Ying Zheng, Ya;Shekhtman, Alexander;Sheng, Jia
合成了一个新的腙修饰胞苷亚磷酰胺结构单元家族，并将其掺入寡脱氧核苷酸中以构建光可切换的 DNA 链。通过 1 H NMR 光谱和 HPLC 在核苷和寡脱氧核苷酸的背景下研究并证实了波长为 450 nm 的蓝光照射引发的 E-Z 异构化。通过使用 BstDNA 聚合酶，发现这种具有六元分子内氢键的腙-胞苷的光激活 Z 型异构体可以抑制引物延伸模型中的 DNA 合成。此外，腙修饰导致 dATP 和 dGTP 以类似的选择性错误掺入生长中的 DNA 链，突出了潜在的 G 到 A 突变。这项工作提供了一种新颖的功能性 DNA 构建模块和一种额外的分子工具，具有潜在的化学生物学和生物医学应用，可利用细胞友好的蓝光照射来控制 DNA 合成和 DNA 酶相互作用。
A new family of hydrazone modified cytidine phosphoramidite building block was synthesized and incorporated into oligodeoxynucleotides to construct photoswitchable DNA strands. TheE‐Zisomerization triggered by the irradiation of blue light with a wavelength of 450 nm was investigated and confirmed by1H NMR spectroscopy and HPLC in the contexts of both nucleoside and oligodeoxynucleotide. The light activatedZform isomer of this hydrazone‐cytidine with a six‐member intramolecular hydrogen bond was found to inhibit DNA synthesis in the primer extension model by usingBstDNA polymerase. In addition, the hydrazone modification caused the misincorporation of dATP together with dGTP into the growing DNA strand with similar selectivity, highlighting a potential G to A mutation. This work provides a novel functional DNA building block and an additional molecular tool that has potential chemical biology and biomedicinal applications to control DNA synthesis and DNA‐enzyme interactions using the cell friendly blue light irradiation.