Kinetics of amide and peptide cleavage by alkaline hydrogen peroxide

The hydroperoxide anion cleaves unactivated amides and peptides although it is completely unreactive toward ethyl esters. The cleavage by HO2(-) proceeds faster than by OH(-) and involves additional routes with general acid assistance by H2O2 and general base assistance by OH(-) and HO2(-). Cleavage of polypeptides occurs at the N-terminal peptide bond. reaction: see text]