Design and Synthesis of Biaryl DNA-Encoded Libraries

ACS Comb Sci. 2016 Oct 10;18(10):625-629. doi: 10.1021/acscombsci.6b00078. Epub 2016 Sep 1.

Abstract

DNA-encoded library technology (ELT) is a powerful tool for the discovery of new small-molecule ligands to various protein targets. Here we report the design and synthesis of biaryl DNA-encoded libraries based on the scaffold of 5-formyl 3-iodobenzoic acid. Three reactions on DNA template, acylation, Suzuki-Miyaura coupling and reductive amination, were applied in the library synthesis. The three cycle library of 3.5 million diversity has delivered potent hits for phosphoinositide 3-kinase α (PI3Kα).

Keywords: DNA-encoded library technology; Suzuki−Miyaura cross-coupling.

MeSH terms

  • Acylation
  • Amination
  • Combinatorial Chemistry Techniques
  • DNA / chemistry*
  • Humans
  • Iodobenzoates / chemistry*
  • Ligands
  • Phosphatidylinositol 3-Kinases / chemistry*
  • Small Molecule Libraries / chemical synthesis*
  • Structure-Activity Relationship

Substances

  • Iodobenzoates
  • Ligands
  • Small Molecule Libraries
  • DNA
  • Phosphatidylinositol 3-Kinases