Thiol-Ene click reactions - Versatile tools for the modification of unsaturated amino acids and peptides

Abstract

Terminal γ,δ-unsaturated amino acids, easily available by Claisen rearrangement or palladium-catalysed allylic alkylation, are excellent substrates for radical thiol additions. These click reactions allow the introduction of highly functionalized side-chains into a given amino acid or peptide. This protocol is suitable for the modification of all kinds of terminal alkenes, such as allyl protecting groups. Terminal γ,δ-unsaturated amino acids and peptides, easily available by Claisen rearrangement or palladium-catalysed allylic alkylation, are excellent substrates for radical thiol additions. These click reactions allow the introduction of highly functionalized side-chains into a given amino acid or peptide. This protocol is also suitable for the modification of allyl protecting groups. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.