Synthesis and structure of symmetrical bicyclic hexapeptides bridged by metathesis reaction |
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Authors: | Giovannoni Jérôme Didierjean Claude Durand Philippe Marraud Michel Aubry André Renaut Patrice Martinez Jean Amblard Muriel |
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Institution: | LAPP, CNRS-UMR 5810, Universités de Montpellier I et II, 15 Avenue Charles Flahault, BP 14 491, 34093 Montpellier Cedex 5, France. |
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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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