Synthesis and Structure of Symmetrical Bicyclic Hexapeptides Bridged by Metathesis Reaction - Université de Lorraine Access content directly
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.
No file

Dates and versions

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

Identifiers

Cite

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⟩
21 View
0 Download

Altmetric

Share

Gmail Facebook X LinkedIn More