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© Institut Pasteur/Antoinette Ryter
Coupe de Mycobacterium bovis ou bacille de Calmette et Guérin (BCG). Souche atténuée de bacille vivant, à l'origine du vaccin antituberculeux délivré par voie intradermique ou scarifications (Grossissement X 70000). Image colorisée.
Publication : Organic & biomolecular chemistry

Modular total syntheses of mycolactone A/B and its [(2)H]-isotopologue

Team: Immunobiology and Therapy
Member: Caroline Demangel
Scientific Fields
Diseases
Organisms
Applications
Technique

Published in Organic & biomolecular chemistry - 20 Sep 2017

Saint-Auret S, Abdelkafi H, Le Nouen D, Guenin-Macé L, Demangel C, Bisseret P, Blanchard N

Link to Pubmed [PMID] – 28871293

Org. Biomol. Chem. 2017 Sep;15(36):7518-7522

A modular total synthesis of mycolactone A/B, the exotoxin produced by Mycobacterium ulcerans, has been achieved through the orchestration of several Pd-catalyzed key steps. While this route leads to a mixture of the natural product and its C12 epimer (4 : 1 ratio), this was inconsequential from the biological activity standpoint. Compared to the previously reported routes, this synthetic blueprint allows the late-stage modification of the toxin, as exemplified by the preparation of [22,22,22-(2)H3]-mycolactone A/B.