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Updated: Dec 25, 2025

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
Published on: September 28, 2022
Side-Chain Modification of Peptides Using a Phosphoranylidene Amino Acid
Enaam Masri1, Ahsanullah1,2, Matteo Accorsi1
1Department of Chemistry, Biology, and Pharmacy, Institute of Pharmacy/Medicinal Chemistry, Freie Universität Berlin, Königin-Luise-Strasse 2 + 4, 14195 Berlin, Germany.
Abstract:
The flexible variation of peptidomimetics is of great interest for the identification of optimized protein ligands. Here we present a general concept for introducing side-chain modifications into peptides using triarylphosphonium amino acids. Building blocks 4a and 4b are activated for amidation and incorporated into stable peptides. The obtained phosphoranylidene peptides undergo Wittig olefinations and 1,3-dipolar cycloaddition reactions, yielding peptidomimetics with vinyl ketones and 5-substituted 1,2,3-triazoles as non-native peptide side chains.
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