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Journal Articles Letters in Peptide Science Year : 1995

Synthesis and conformational analysis of AzAsx-containing oligopeptides

Abstract

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 AzAsx-dipeptide 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 β-fold, unlike the cognate dipeptide which adopts an Asx-turn.

Dates and versions

hal-03995838 , version 1 (18-02-2023)

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Frédéric André, Guy Boussard, Michel Marraud, Claude Didierjean, André Aubry. Synthesis and conformational analysis of AzAsx-containing oligopeptides. Letters in Peptide Science, 1995, 2 (3-4), pp.239-242. ⟨10.1007/BF00119162⟩. ⟨hal-03995838⟩
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