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

Bioconjug Chem. 2020 Sep 16;31(9):2092-2097. doi: 10.1021/acs.bioconjchem.0c00392. Epub 2020 Aug 20.

Abstract

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.

MeSH terms

  • Aldehydes / chemical synthesis
  • Aldehydes / chemistry*
  • Amides / chemical synthesis
  • Amides / chemistry*
  • Amines / chemistry*
  • Aniline Compounds / chemistry
  • Catalysis
  • Copper / chemistry*
  • DNA / chemistry*
  • Oxidation-Reduction

Substances

  • Aldehydes
  • Amides
  • Amines
  • Aniline Compounds
  • Copper
  • DNA