Qu Yi, Wen Huanan, Ge Rui, Xu Yanfen, Gao Hong, Shi Xiaodong, Wang Jiangong, Cui Weiren, Su Wenji, Yang Hongfang, Kuai Letian, Satz Alexander L, Peng Xuanjia
HitS Business Unit, WuXi AppTec, 288 Fute Zhong Road, Waigaoqiao Free Trade Zone, Shanghai 200131, China.
Org Lett. 2020 Jun 5;22(11):4146-4150. doi: 10.1021/acs.orglett.0c01219. Epub 2020 May 8.
We report a DNA-compatible copper-mediated efficient synthesis of 1,2,3-triazoles via a one-pot reaction of aryl borates with TMS-N followed by a click cycloaddition reaction. Employing the binuclear macrocyclic nanocatalyst Cu(II)-β-cyclodextrin, the reactions were performed under mild conditions with high conversions and wide functional group tolerance. We also demonstrate the reaction application toward a one-pot DNA-compatible intramolecular macrocyclization. Our optimized reaction protocol results in no significant DNA damage as judged by qPCR analysis and Sanger sequencing data.
我们报道了一种通过芳基硼酸酯与TMS-N的一锅反应，随后进行点击环加成反应，实现与DNA兼容的铜介导的1,2,3-三唑高效合成。使用双核大环纳米催化剂Cu(II)-β-环糊精，反应在温和条件下进行，具有高转化率和广泛的官能团耐受性。我们还展示了该反应在一锅法与DNA兼容的分子内大环化中的应用。根据qPCR分析和桑格测序数据判断，我们优化的反应方案不会造成显著的DNA损伤。
