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Updated: May 16, 2026

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
Published on: September 28, 2022
Synthesis of cyclically constrained sugar derived α/β- and α/γ-peptides
Antonio Franconetti1, Sorel Jatunov, Pastora Borrachero
1Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, C/Profesor García González 1, 41012 Sevilla, Spain.
Abstract:
A general approach to enantiopure conformationally constrained sugar derived α/β- and α/γ-peptides has been established. Five-membered ring α/β-peptides were synthesized via formyl C-glycofuranosides, easy available from hexose-derived azido-2-equatorial-OH-glycopyranosides by DAST-promoted ring contraction. By means of a regioselective oxidation with TEMPO at C-6 of hexose-derived 3-azido glycopyranosides as the key step, two- and three-residue α/γ-peptides having a six-membered ring were obtained in good yields and under very simple experimental conditions.
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