Late-stage lipidation of peptides via aqueous thiol-michael addition to dehydroalanine (Dha)

Abstract

This work presents a late-stage aqueous peptide lipidation strategy via the thiol-Michael addition of thiolated lipids at dehydroalanine (Dha). This strategy was used to synthesise lipopeptides containing diacylglycerol (DAG), saturated, unsaturated and cholesterol lipid motifs. The DAG lipopeptide product was found to be a substrate for the lipoprotein processing enzyme, LspA.