The occurrence of ansamers in the synthesis of cyclic peptides

Guiyang Yao, Simone Kosol, Marius T. Wenz, Elisabeth Irran, Bettina G. Keller, Oliver Trapp and Roderich D. Süssmuth ()
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Guiyang Yao: Technische Universität Berlin
Simone Kosol: Technische Universität Berlin
Marius T. Wenz: Freie Universität Berlin
Elisabeth Irran: Technische Universität Berlin
Bettina G. Keller: Freie Universität Berlin
Oliver Trapp: Ludwig-Maximilians-University
Roderich D. Süssmuth: Technische Universität Berlin

Nature Communications, 2022, vol. 13, issue 1, 1-8

Abstract: Abstract α-Amanitin is a bicyclic octapeptide composed of a macrolactam with a tryptathionine cross-link forming a handle. Previously, the occurrence of isomers of amanitin, termed atropisomers has been postulated. Although the total synthesis of α-amanitin has been accomplished this aspect still remains unsolved. We perform the synthesis of amanitin analogs, accompanied by in-depth spectroscopic, crystallographic and molecular dynamics studies. The data unambiguously confirms the synthesis of two amatoxin-type isomers, for which we propose the term ansamers. The natural structure of the P-ansamer can be ansa-selectively synthesized using an optimized synthetic strategy. We believe that the here described terminology does also have implications for many other peptide structures, e.g. norbornapeptides, lasso peptides, tryptorubins and others, and helps to unambiguously describe conformational isomerism of cyclic peptides.

Date: 2022
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DOI: 10.1038/s41467-022-34125-8

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