S-deoxo-Abu1,Ile3-amaninamide, an inactive amatoxin analogue.

G Zanotti, T Wieland, G D'Auria, L Paolillo, E Trivellone

CNR, Department of Pharmaceutical Sciences, University La Sapienza, Rome, Italy.

International journal of peptide and protein research 1990 Mar

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The title compound 3, an amatoxin analogue containing L-alpha-aminobutyric acid instead of L-asparagine in position 1, as in natural toad stool peptides, has been synthesized. It does not inhibit the eukaryotic DNA-dependent RNA polymerase form II (or B) in concentrations up to 10(-4)M, whereas 50% inhibition is exerted in 10(-6)M solution by the corresponding Asn-analogue S-deoxo-Ile3-amaninamide 2. The striking difference seems to be due to a relatively small variation of the conformation recognized by sensitive NMR spectroscopic methods.

Citation

G Zanotti, T Wieland, G D'Auria, L Paolillo, E Trivellone. S-deoxo-Abu1,Ile3-amaninamide, an inactive amatoxin analogue. International journal of peptide and protein research. 1990 Mar;35(3):263-70