Jump to main content
Jump to site search


Synthesis of DNA-coupled isoquinolones and pyrrolidines by solid phase ytterbium- and silver-mediated imine chemistry

Author affiliations

Abstract

DNA-encoded libraries of chemically synthesized compounds are an important small molecule screening technology. The synthesis of encoded compounds in solution is currently restricted to a few DNA-compatible and water-tolerant reactions. Encoded compound synthesis of short DNA-barcodes covalently connected to solid supports benefits from a broad range of choices of organic solvents. Here, we show that this encoded chemistry approach allows for the synthesis of DNA-coupled isoquinolones by an Yb(III)-mediated Castagnoli–Cushman reaction under anhydrous reaction conditions and for the synthesis of highly substituted pyrrolidines by Ag(I)-mediated 1,3-dipolar azomethine ylide cycloaddition. An encoding scheme for these DNA-barcoded compounds based on a DNA hairpin is demonstrated.

Graphical abstract: Synthesis of DNA-coupled isoquinolones and pyrrolidines by solid phase ytterbium- and silver-mediated imine chemistry

  • This article is part of the themed collection: New Talent
Back to tab navigation

Supplementary files

Publication details

The article was received on 25 Jan 2019, accepted on 21 Feb 2019 and first published on 26 Feb 2019


Article type: Research Article
DOI: 10.1039/C9MD00042A
Citation: Med. Chem. Commun., 2019, Advance Article

  •   Request permissions

    Synthesis of DNA-coupled isoquinolones and pyrrolidines by solid phase ytterbium- and silver-mediated imine chemistry

    M. Potowski, V. B. K. Kunig, F. Losch and A. Brunschweiger, Med. Chem. Commun., 2019, Advance Article , DOI: 10.1039/C9MD00042A

Search articles by author

Spotlight

Advertisements