On-DNA Palladium-Catalyzed Hydrogenation-like Reaction Suitable for DNA-Encoded Library Synthesis

Bioconjug Chem. 2021 Jan 20;32(1):88-93. doi: 10.1021/acs.bioconjchem.0c00566. Epub 2020 Dec 24.

Abstract

Herein we describe a method to orthogonally remove on-DNA N-Cbz, N-Alloc, N-Allyl, O-Bn, and O-Allyl protecting groups in the presence of other common protecting groups to afford free amines and carboxylic acids, respectively. The developed method uses NaBH4 as the source of hydrogen in the presence of Pd(OAc)2 under DNA aqueous conditions. In addition, under the developed conditions we were able to successfully hydrogenate triple and double bonds to totally saturated compounds. Furthermore, we introduce a new alternative procedure to reduce azides and aromatic nitro compounds to primary amines.

MeSH terms

  • Catalysis
  • DNA / chemistry*
  • Gene Library
  • Hydrogen / chemistry
  • Palladium / chemistry*

Substances

  • Palladium
  • Hydrogen
  • DNA