Prof. Jean-Marc Campagne
Prof. Jean-Marc Campagne
University of Montpellier, France
Peptides are attracting increasing attention on different fields such as medicinal chemistry, polymers and materials science. While these molecules are naturally built up from the N→C direction, they are chemically synthesized from the opposite direction (C→N). Indeed, the traditional synthesis proceeds through the activation of the carboxylic acid moiety of a first aminoacid, by means of coupling reagents, allowing the nucleophilic attack of the amino partner of a second aminoacid with concomitant formation of the amide bond (Scheme 1, a).1 Although very efficient, these coupling reagent strategies suffer from some drawbacks, notably those associated with epimerization. So, we embarked on a program aiming to synthesize amides for application in peptide synthesis via the activation of the amine function instead of the carboxylic acid (Scheme 1, b). By doing so, we wish to avoid some inherent problems found on classic peptide synthesis (e.g. epimerization) and also to approach from the natural synthesis of peptides (N→C direction).

Scheme 1: Peptide synthesis

The use of N,N’-carbonyldiimidazole (CDI) for the preparation of unprecedented activated-aminoesters, and their transformations into several dipeptides and tripeptides will be discussed (Scheme 2). 2

Scheme 2: Dipeptide Syntheses via Activated α-Aminoesters
Jean-Marc Campagne is a Professor of Organic Chemistry at the Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM). After studies at the Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM), he received his Ph.D. at the University of Montpellier in 1994 dealing with the production of catalytic antibodies. After post-doctoral training with Prof B. Trost (Stanford University, USA) and Prof. L. Ghosez (Université Catholique de Louvain, Belgium), he was appointed CNRS researcher at the Institut de Chimie des Substances Naturelles in Gif-sur-Yvette in 1998. Since 2005 he moved to the ENSCM where he was appointed as Professor. His current interests concern the development of methodologies in organic synthesis and their application to the total synthesis of natural products. He has published around 100 papers in journals, books and conference proceedings.