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Updated: Apr 13, 2026
Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
Published on: September 28, 2022
Peptide macrocycles featuring a backbone secondary amine: a convenient strategy for the synthesis of lipidated cyclic
Alberto Oddo1, Lena Münzker1, Paul R Hansen1
1Department of Drug Design and Pharmacology, University of Copenhagen, Universitetsparken 2, 2100, Copenhagen, Denmark.
Abstract:
A convenient strategy for the on-resin synthesis of macrocyclic peptides (3- to 13-mers) via intramolecular halide substitution by a diamino acid is described. The method is compatible with standard Fmoc/tBu SPPS and affords a tail-to-side-chain macrocyclic peptide featuring an endocyclic secondary amine. This functional group is still reactive toward acylation, allowing for the continuation of the synthesis. An application to the synthesis of lipidated cyclic and bicyclic antimicrobial peptides is presented.
