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Scaling Amatoxin Synthesis with an Improved Route to (2S,3R,4R)‑Dihydroxyisoleucine Exemplified by a Toxic, Clickable α‑Amanitin Analogue

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journal contribution
posted on 12.03.2021, 19:06 by Chido M. Hambira, Kaveh Matinkhoo, Alla Pryyma, Brian O. Patrick, David M. Perrin
Here we report a scalable synthesis of the key amino acid residue, (2S,3R,4R)-4,5-dihydroxyisoleucine (DHIle) in α-amanitin, that in turn enables the scalable synthesis of an equipotent analogue, Asn(N‑ethylazide)-S,6′-dideoxy-α-amanitin, suitable for CuAAC conjugation to empower studies on therapeutic antibody-drug conjugates.