Amatoxin - Structure

Structure

The compounds have a similar structure, that of eight amino-acid residues arranged in a conserved macrobicyclic motif (an overall pentacyclic structure when counting the rings inherent in the proline and tryptophan-derived residues); they were isolated in 1941 by Heinrich O. Wieland and Rudolf Hallermayer of the University of Munich. All amatoxins are oligopeptides that are synthesized as 35-amino-acids-long proproteins, from which the final eight amino acids are cleaved by a prolyl oligopeptidase.

There are currently ten known amatoxins:

Name R1 R2 R3 R4 R5
α-Amanitin OH OH NH2 OH OH
β-Amanitin OH OH OH OH OH
γ-Amanitin H OH NH2 OH OH
ε-Amanitin H OH OH OH OH
Amanullin H H NH2 OH OH
Amanullinic acid H H OH OH OH
Amaninamide OH OH NH2 H OH
Amanin OH OH OH H OH
Proamanullin H H NH2 OH H

δ-Amanitin has been reported, but its chemical structure has not been determined.

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