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Updated: Mar 26, 2026

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
Published on: September 28, 2022
Allene Functionalized Azobenzene Linker Enables Rapid and Light-Responsive Peptide Macrocyclization
Mohammad R Jafari1, Jenner Lakusta1, Rylan J Lundgren1
1Department of Chemistry and ‡Alberta Glycomics Centre, University of Alberta , Edmonton, Alberta T6G 2G2, Canada.
Abstract:
In this manuscript, we describe the efficient synthesis of a bis(allenamide) functionalized water-soluble azobenzene reagent (BSBDA) and its application as a new tool for the rapid generation of visible light-responsive macrocyclic peptides and peptide libraries displayed on the surface of bacteriophage. The allenamide functionality promotes cysteine ligation in model peptides and those displayed on phage with rates 2-3 orders of magnitude faster than the established alkyl halide containing azobenzenes.
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