Enhancing the Potential of Miniature-Scale DNA-Compatible Radical Reactions via an Electron Donor–Acceptor Complex and a Reversible Adsorption to Solid Support Strategy,Organic Letters

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Enhancing the Potential of Miniature-Scale DNA-Compatible Radical Reactions via an Electron Donor–Acceptor Complex and a Reversible Adsorption to Solid Support Strategy
Organic Letters ( IF 4.9 ) Pub Date : 2021-09-21 , DOI: 10.1021/acs.orglett.1c02562
Bizhen Lin ₁ , Weiwei Lu ₂ , Zhen-Yu Chen ₃ , Yue Zhang ₁ , Yin-Zhe Duan ₁ , Xiaojie Lu ₂ , Ming Yan ₁ , Xue-Jing Zhang ₁

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DNA-encoded library (DEL) technology is a powerful tool in the discovery of bioactive probe molecules and drug leads. Mostly, the success in DEL technology stems from the molecular diversity of the chemical libraries. However, the construction of DELs has been restricted by the idiosyncratic needs and the required low concentration (∼1 mM or less) of the library intermediate. Here, we report visible-light-promoted on-DNA radical coupling reactions via an electron donor–acceptor (EDA) complex and a reversible adsorption to solid support (RASS) strategy. This protocol provides a unique solution to the challenges of increasing the reactivity of highly diluted DNA substrates and reducing the residues of heavy metals from photocatalysts. A series of on-DNA indole sulfone and selenide derivatives were obtained with good to quantitative conversions. It is anticipated that these mild-condition on-DNA radical reactions will significantly improve the chemical diversity of DELs and find widespread utility to DEL construction.

中文翻译：

通过电子供体-受体复合物和固体支持策略的可逆吸附增强微型 DNA 兼容自由基反应的潜力

DNA 编码文库 (DEL) 技术是发现生物活性探针分子和药物先导物的有力工具。大多数情况下，DEL 技术的成功源于化学库的分子多样性。然而，DEL 的构建受到特殊需求和所需的低浓度（~1 mM 或更低）的库中间体的限制。在这里，我们报告了可见光促进的 DNA 自由基偶联反应，通过电子供体 - 受体 (EDA) 复合物和固体载体的可逆吸附 (RASS) 策略。该协议为提高高度稀释的 DNA 底物的反应性和减少光催化剂中重金属残留的挑战提供了独特的解决方案。获得了一系列具有良好到定量转化的 DNA 上吲哚砜和硒化物衍生物。

更新日期：2021-10-01

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