Corramycin
Researchers at Sanofi isolated this secondary metabolite from the myxobacterium Corallococcus coralloides. In collaboration with the Müller group, they elucidated the structure and biosynthesis and reported the first total synthesis based entirely on solid-phase peptide synthesis (SPPS). Corramycin shows notable bioactivity against gram-negative bacteria both in vitro and in vivo. In addition, the lack of cross-resistance with standard antibiotic classes, such as carbapenems, amino-glycosides, or quinolones, and efficacy in a mouse model makes it an attractive target for further exploration.
- C. Couturier, S. Groß, A. von Tesmar, J. Hoffmann, S. Deckarm, et al., Angew. Chem. Int. Ed. 2022, 61, e202210747.
A ligation-mediated total synthesis of corramycin was developed. The synthetic strategy included using two consecutive chemical ligations for a modular and efficient preparation. Finally, the synthesis employed a Ser/Thr ligation (STL) at a new ligation site combined with classical fragment coupling. This study provides the total synthesis of corramycin and enhances the preparative toolbox of STL in organic synthesis.
- A. Siebert, U. Kazmaier, "Chemical Ligation-Mediated Total Synthesis of Corramycin", Org. Lett. 2024, 26, 3169-3173. DOI: 10.1021/acs.orglett.4c00774.