The Preparation of Solid-Supported Peptide Boronic Acids Derived from 4-Borono-L-phenylalanine and their Affinity for Alizarin

Abstract

A library of solid-supported pentapeptide diboronic acids, a ‘lysine series’ and an ‘arginine series’, has been efficiently prepared using N-Fmoc-4-pinacolatoborono-l-phenylalanine and standard solid phase peptide synthesis methods. A technique for measuring the affinity of the chromophoric diol, alizarin, to the solid-supported peptide boronic acids has been developed. Considerable variation in alizarin binding strengths, both within and between arginine and lysine series was observed, with association constants in the range 200–1100 M–1 being recorded. The selective binding characteristics of these boronic acid–peptide hybrids suggest their potential use in carbohydrate sensors and cell-specific diagnostics and therapeutics.