Synthesis of analogues of amaninamide, an amatoxin from the white Amanita 
virosa mushroom

Zanotti, Giancarlo; Möhringer, Claudius; Wieland, Theodor

doi:10.1111/j.1399-3011.1987.tb03353.x

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Synthesis of analogues of amaninamide, an amatoxin from the white Amanita virosa mushroom

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Wieland, Theodor
Max Planck Institute for Medical Research, Max Planck Society;

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Citation

Zanotti, G., Möhringer, C., & Wieland, T. (1987). Synthesis of analogues of amaninamide, an amatoxin from the white Amanita virosa mushroom. International journal of peptide and protein research, 30(4), 450-459. doi:10.1111/j.1399-3011.1987.tb03353.x.

Cite as: https://hdl.handle.net/21.11116/0000-000A-53C1-E

Abstract

Analogs of amaninamide, due to the absence of a 6-hydroxy group in the tryptophan moiety, are more easily accessible by synthesis than derivatives of α-amanitin. Syntheses of bicyclic octapeptide thioethers 1f-1m have been carried out starting from linear Hpi-S-trityl-octapeptides (3), cyclization by intramolecular 2′-indolylthioether formation yielding monocyclic peptides (2) and final cyclization by DCCI. One of the bicyclic thioethers was oxidized to yield the corresponding chromatographically separated (R)- and (S)-sulfoxides, respectively. The products were characterized by RF-values, u.v. and CD spectra as well as by mass (FAB) spectroscopy. The widely differing inhibitory activities on RNA polymerase II (or B) from calf thymus are listed.