Solid-phase synthesis of peptide β-aminoboronic acids

Abstract

Peptide/boronic acid conjugates are attractive scaffolds for chemical probe discovery and drug design. There are only a few reactions that allow for rapid incorporation of boron into peptides. Herein, we report a new approach towards the synthesis of peptide β-aminoboronic acids on solid support using 2-chlorotrityl resin and solid-phase peptide synthesis techniques with only one purification required. Evaluation of model compounds demonstrate the stability of peptide boronic acids toward degradation at physiological pH. This straightforward conjugation process should allow access to a wide range of peptide boronic acid scaffolds for both synthetic and medicinal use.