DOI: 10.1021/acs.jnatprod.6c00782 ISSN: 0163-3864
Genome Mining and Total Synthesis of Viduamanide, A Non-canonical Prolineless Cycloamanide from Amanita vidua
Adrien Jagora, Thomas Charpentier, Tom Lorthios, Pablo Tris, Pierre-Arthur Moreau, Jean-Michel Bellanger, Jean-François Gallard, Rémi Franco, Blandine Séon-Méniel, Antonia Gasch Illescas, Thierry Milcent, Mehdi A. Beniddir, Pierre Le PogamAbstract
The MeOH extract of the newly described deadly mushroom Amanita vidua was dominated by an unknown peptide. Despite the limited fungal material available, the compound was isolated and characterized as a homodetic cyclic hexapeptide by NMR and MS/MS analyses, and its structure was confirmed by high-efficiency solid-phase peptide synthesis. Recently implemented genome mining further validated the structure and provided a broader insight into the cyclopeptide-producing capabilities of this rare mushroom. Named viduamanide, this compound is a non-canonical cycloamanide of the “prolineless” subtype and the first of its kind ever reported to not contain a proline residue.