Structure-toxicity relationships in the amatoxin series. Structural variations of side chain 3 and inhibition of RNA polymerase II.

@article{Zanotti1992StructuretoxicityRI,
  title={Structure-toxicity relationships in the amatoxin series. Structural variations of side chain 3 and inhibition of RNA polymerase II.},
  author={Giancarlo Zanotti and Gabriele Petersen and Theodor Wieland},
  journal={International journal of peptide and protein research},
  year={1992},
  volume={40 6},
  pages={
          551-8
        }
}
The amatoxins, highly toxic components of death cap Amanita mushrooms, bind strongly to RNA polymerase II (or B) in cell nuclei thus preventing the transcription of DNAs to hn-RNAs (Pre-mRNAs), the precursors of messenger RNAs. Three of the binding sites of the bicyclic octapeptides have been identified: an isoleucine side chain in position 6, a trans-4-hydroxyl group at proline in position 2 and a hydroxylated L-isoleucine side chain in position 3. No information exists about the… Expand
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The synthesis of an analog bearing a gamma-hydroxyl group in the isoleucine side chain is described and was found to have about the same inhibitory effect on RNA polymerase II from Drosophila embryos as amanullin and the Ile3-analog 7. Expand
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S-deoxo-Abu1,Ile3-amaninamide, an inactive amatoxin analogue.
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 theExpand
RNA Polymerase B from Drosophila melanogaster Larvae
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When the antiserum was added to Drosophila RNA polymerase B at different stages of the purification, the resulting precipitates were found to contain nearly constant proportions of seven of the ten polypeptides present in the purified enzyme. Expand
Über die Inhaltsstoffe des grünen Knollenblätterpilzes, XL. Oxydation und Reduktion an der γ.δ‐Dihydroxy‐isoleucin‐Seitenkette des O‐Methyl‐α‐amanitins. Methyl‐aldoamanitin, ein ungiftiges Abbauprodukt
Die γ.δ-Dihydroxy-isoleucin-Seitenkette des O-Methyl-α-amanitins (1b) laβt sich durch kurze Perjodatoxydation zum Aldehyd 2 mit einem C-Atom weniger abbauen; O-Methyl-aldoamanitin (2) ist ungiftig.Expand
Über die Inhaltsstoffe des grünen Knollenblätterpilzes, XLVI1) Das zum giftigen O‐Methylamanitin diastereomere ungiftige Sulfoxid
Das an der phenolischen OH-Gruppe methylierte, giftige α-Amanitin (O-Methyl-α-amanitin, 1b) wird mit Raney-Nickel zum ebenfalls giftigen O-Methyl-S-desoxo-α-amanitin (Thioather 1a) reduziert.Expand
Über die Inhaltsstoffe des grünen Knollenblätterpilzes, XLVII1) Proamanullin und Amanullinsäure sowie zwei unbekannte Derivate des β‐Amanitins; die restlichen Mitglieder der Amanitinfamilie
Es wird uber die Isolierung und soweit wie mogliche Charakterisierung einiger in winziger Menge im Methanolextrakt von Amanita phalloides enthaltenen Vertreter der Amanitinfamilie berichtet:Expand