DNA-Compatible Copper-Catalyzed Oxidative Amidation
of Aldehydes with Non-Nucleophilic Arylamines

Li, Ke; Qu, Yi; An, Yulong; Breinlinger, Eric; Webster, Matthew P.; Wen, Huanan; Ding, Duanchen; Zhao, Meng; Shi, Xiaodong; Wang, Jiangong; Su, Wenji; Cui, Weiren; Satz, Alexander L.; Yang, Hongfang; Kuai, Letian; Little, Andrew; Peng, Xuanjia

doi:10.1021/acs.bioconjchem.0c00392.s001

bc0c00392_si_001.pdf (4.56 MB)

DNA-Compatible Copper-Catalyzed Oxidative Amidation of Aldehydes with Non-Nucleophilic Arylamines

journal contribution

posted on 2020-08-20, 15:41 authored by Ke Li, Yi Qu, Yulong An, Eric Breinlinger, Matthew P. Webster, Huanan Wen, Duanchen Ding, Meng Zhao, Xiaodong Shi, Jiangong Wang, Wenji Su, Weiren Cui, Alexander L. Satz, Hongfang Yang, Letian Kuai, Andrew Little, Xuanjia Peng

We report a DNA-compatible protocol for synthesizing amides from DNA-bound aldehydes and non-nucleophilic arylamines including aza-substituted anilines, 2-aminobenzimidazoles, and 3-aminopyrazoles. The reactions were carried out at room temperature and provided reasonable conversions and wide functional group compatibility. The reactions were also successful when employing aryl and aliphatic aldehydes. In addition, qPCR and NGS data suggested no negative impact on DNA integrity after the copper-mediated oxidative amidation reaction.

DNA-Compatible Copper-Catalyzed Oxidative Amidation of Aldehydes with Non-Nucleophilic Arylamines

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