Huang-Chi Du; Nicholas Simmons; John C. Faver; Zhifeng Yu; Murugesan Palaniappan; Kevin Riehle; Martin M. Matzuk
Org. Lett., 2019, 21, 7, 2194-2199
https://doi.org/10.1021/acs.orglett.9b00497

Abstract

A hypodiboric acid system for the reduction of nitro groups on DNA–chemical conjugates has been developed. This transformation provided good to excellent yields of the reduced amine product for a variety of functionalized aromatic, heterocyclic, and aliphatic nitro compounds. DNA tolerance to reaction conditions, extension to decigram scale reductions, successful use in a DNA-encoded chemical library synthesis, and subsequent target selection are also described.