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Synthesis of the Death-Cap Mushroom Toxin α-Amanitin

Synthesis of the Death-Cap Mushroom Toxin α-Amanitin

Kaveh Matinkhoo, Alla Pryyma, Mihajlo Todorovic, Brian O Patrick, David M Perrin

J Am Chem Soc. 2018 May 30;140(21):6513-6517.

PMID: 29561592

Abstract:

α-Amanitin is an extremely toxic bicyclic octapeptide isolated from the death-cap mushroom, Amanita phalloides. As a potent inhibitor of RNA polymerase II, α-amanitin is toxic to eukaryotic cells. Recent interest in α-amanitin arises from its promise as a payload for antibody-drug conjugates. For over 60 years, A. phalloides has been the only source of α-amanitin. Here we report a synthesis of α-amanitin, which surmounts the key challenges for installing the 6-hydroxy-tryptathionine sulfoxide bridge, enantioselective synthesis of (2 S,3 R,4 R)-4,5-dihydroxy-isoleucine, and diastereoselective sulfoxidation.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP23109059	α-Amanitin		23109-05-9	Price

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