Journal Articles Organic Letters Year : 2004

Synthesis and Structure of Symmetrical Bicyclic Hexapeptides Bridged by Metathesis Reaction

Abstract

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 β-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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hal-03996498 , version 1 (20-02-2023)

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Jérôme Giovannoni, Claude Didierjean, Philippe Durand, Michel Marraud, André Aubry, et al.. Synthesis and Structure of Symmetrical Bicyclic Hexapeptides Bridged by Metathesis Reaction. Organic Letters, 2004, 6 (20), pp.3449-3452. ⟨10.1021/ol0487940⟩. ⟨hal-03996498⟩
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