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Updated: Aug 22, 2026

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
Published on: September 28, 2022
Synthesis and structure of symmetrical bicyclic hexapeptides bridged by metathesis reaction
Jérôme Giovannoni1, Claude Didierjean, Philippe Durand
1LAPP, CNRS-UMR 5810, Universités de Montpellier I et II, 15 Avenue Charles Flahault, BP 14 491, 34093 Montpellier Cedex 5, France.
Abstract:
[structure: see text] Bicyclic hexapeptides 1a-c were synthesized via an intramolecular ring-closing metathesis reaction on solid phase followed by an N- to C-terminal cyclization in solution. Structural elucidation showed that these compounds assumed a C2-symmetrical structure with two beta-turns. The trans-ethylene plane was found to occupy two positions in rapid interconversion. One of the bicyclic hexapeptides crystallized with five water molecules, which made an arch above the ethylene group.
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