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Synthesis and conformational analysis of AzAsx-containing oligopeptides

✍ Scribed by Frédéric André; Guy Boussard; Michel Marraud; Claude Didierjean; André Aubry

Publisher
Springer Netherlands
Year
1995
Tongue
English
Weight
233 KB
Volume
2
Category
Article
ISSN
1573-3149

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✦ Synopsis

For the sake of improving synthetic methods and evaluating the conformational perturbation induced by the substitution of AzAsx for the Asx residue in the cognate dipeptide R-CO-Asx-Pro-NHR', we prepared the AzAsxdipeptide sequence by making use of the crystalline triphosgene. This reagent allows, in situ and under very mild experimental conditions, both the carbonylation and the activation of the properly substituted and N-protected hydrazine before coupling with the proline partner. With regard to conformational behaviour, the azadipeptide sequence displays a 13-fold, unlike the cognate dipeptide which adopts an Asx-turn.

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