Inverse peptide synthesis via activated α-aminoesters.
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.
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).
Jean-Simon
JS
Suppo
Gilles
G
Subra
Matthieu
M
Bergès
Renata
R
Marcia de Figueiredo
Jean-Marc
JM
Campagne
D000577:Amides / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry; D004952:Esters; D007536:Isomerism; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry
D000577:Amides; D000596:Amino Acids; D002264:Carboxylic Acids; D004952:Esters; D009842:Oligopeptides
amides; amino acids; epimerization; peptides; synthetic methods