Inverse Peptide Synthesis via Activated α‐Aminoesters |
| |
Authors: | Jean‐Simon Suppo Prof. Dr. Gilles Subra Matthieu Bergès Dr. Renata Marcia de Figueiredo Prof. Dr. Jean‐Marc Campagne |
| |
Affiliation: | 1. Institut Charles Gerhardt Montpellier (ICGM), UMR 5253 CNRS‐UM2‐UM1‐ENSCM, Ecole Nationale Supérieure de Chimie, 8 Rue de l'Ecole Normale, 34296 Montpellier Cedex 5 (France);2. Institut des Biomolécules Max Mousseron (IBMM), UMR 5257 CNRS‐UM2‐UM1, LAPP‐Faculté de Pharmacie, Avenue Charles Flahault, Bat E, 34093 Montpellier Cedex 5 (France) |
| |
Abstract: | A mild, practical, and simple procedure for peptide‐bond formation is reported. Instead of activation of the carboxylic acid functionality, the reaction involves an unprecedented use of activated α‐aminoesters. The method provides a straightforward entry to dipeptides and was effective when a sensitive cysteine residue was used, as no epimerization was detected in this case. The applicability of this method to iterative peptide synthesis was illustrated by the synthesis of a model tetrapeptide in the challenging reverse N→C direction. |
| |
Keywords: | amides amino acids epimerization peptides synthetic methods |
|
|