1610768-80-3Relevant articles and documents
Inverse peptide synthesis via activated α-aminoesters
Suppo, Jean-Simon,Subra, Gilles,Berges, Matthieu,Marcia De Figueiredo, Renata,Campagne, Jean-Marc
, p. 5389 - 5393 (2014/06/09)
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. How to advance by going into reverse: In a mild and practical procedure for peptide-bond formation, free α-aminoesters were activated by treatment with N,N′-carbonyldiimidazole, instead of activating the carboxylic acid functionality (see scheme). The method provided a straightforward route to dipeptides, and its applicability to iterative peptide synthesis was illustrated by the synthesis of a tetrapeptide in the challenging reverse N→C direction.
