基于DNA-芳香胺偶联物的四唑合成
On-DNA Tetrazole Formation through Conjugation of Anilines
摘要
本文构建了一种DNA兼容的四唑合成策略。以DNA偶联芳胺为底物，利用亚硝酸叔丁酯在温和条件下原位重氮化，生成DNA偶联芳基重氮盐，并与以醛与苯磺酰肼所得腙在碱性条件下发生偶联环化，得到多样化的DNA偶联四唑。该合成策略操作简便且反应条件温和，可引入多种取代基以提升化学多样性。四唑既可作为潜在生物活性片段，也可作为反应前体，与烯烃、羧基和氨基反应。该方法有望用于构建、扩展DNA编码的四唑分子库，为后续筛选活性化合物奠定基础。
Abstract
A DNA-compatible strategy for tetrazole synthesis is reported. DNA-conjugated anilines were used as substrates. In situ diazotization with tert-butyl nitrite (tBuONO) under mild conditions generated DNA-linked aryldiazonium salts. These intermediates underwent base-promoted coupling/cyclization with hydrazones, which were prepared from aldehydes and benzenesulfonyl hydrazide, to afford diverse DNA-conjugated tetrazoles. The protocol is simple to operate and proceeds under mild conditions. It accommodates a wide range of substituents, thereby increasing chemical diversity. The tetrazoles can serve as potential bioactive motifs and as versatile synthetic precursors. They can undergo further transformations with alkenes, carboxyl-containing partners, and amines. Overall, this method enables the construction of expanded DNA-encoded tetrazole libraries and supports downstream screening for active compounds.关键词
DNA兼容反应/四唑/环化/Key words
DNA-compatible reaction/Tetrazole/Cyclization引用本文复制引用
段芸,刘金露,李杨峰,李亦舟.基于DNA-芳香胺偶联物的四唑合成[EB/OL].(2026-03-24)[2026-03-27].http://www.paper.edu.cn/releasepaper/content/202603-239.学科分类
生物科学理论、生物科学方法/生物科学研究方法、生物科学研究技术/生物化学
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