Rapid synthesis and introduction of a protected EDTA-like group during the solid-phase assembly of peptides

Abstract

A simple two-step procedure is reported for the synthesis of a tert-butyl ester protected form of an EDTA-like bifunctional chelating agent. This reagent can be easily introduced on any available amino group during the assembly of peptides on solid-phase supports. Using the model tetradecapeptide OVA(323-336), we have introduced an EDTA group at the N-terminus of this T-cell epitope and confirmed that the EDTA group is present on the molecule, can chelate metals, and does not affect the biological activity of the peptide.