Wikipedia

γ-Amanitin

γ-Amanitin (gamma-Amanitin) is a cyclic peptide of eight amino acids. It is an amatoxin, a group of toxins isolated from and found in several members of the mushroom genus Amanita, one being the death cap (Amanita phalloides) as well as the destroying angel, a complex of similar species, principally A. virosa and A. bisporigera. The compound is highly toxic, inhibits RNA polymerase II, disrupts synthesis of mRNA, and can be fatal.[1]

γ-Amanitin
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C39H54N10O13S/c1-5-16(2)31-36(59)42-12-29(54)43-26-15-63(62)38-22(21-7-6-19(51)8-23(21)46-38)10-24(33(56)41-13-30(55)47-31)44-37(60)32(17(3)18(4)50)48-35(58)27-9-20(52)14-49(27)39(61)25(11-28(40)53)45-34(26)57/h6-8,16-18,20,24-27,31-32,46,50-52H,5,9-15H2,1-4H3,(H2,40,53)(H,41,56)(H,42,59)(H,43,54)(H,44,60)(H,45,57)(H,47,55)(H,48,58)/t16-,17-,18-,20+,24-,25-,26-,27-,31-,32-,63?/m0/s1 checkY
    Key: WVHGJJRMKGDTEC-ZUROAWGWSA-N checkY
  • InChI=1/C39H54N10O13S/c1-5-16(2)31-36(59)42-12-29(54)43-26-15-63(62)38-22(21-7-6-19(51)8-23(21)46-38)10-24(33(56)41-13-30(55)47-31)44-37(60)32(17(3)18(4)50)48-35(58)27-9-20(52)14-49(27)39(61)25(11-28(40)53)45-34(26)57/h6-8,16-18,20,24-27,31-32,46,50-52H,5,9-15H2,1-4H3,(H2,40,53)(H,41,56)(H,42,59)(H,43,54)(H,44,60)(H,45,57)(H,47,55)(H,48,58)/t16-,17-,18-,20+,24-,25-,26-,27-,31-,32-,63?/m0/s1
    Key: WVHGJJRMKGDTEC-ZUROAWGWBF
  • CC[C@H](C)[C@H]1C(=O)NCC(=O)N[C@H]2CS(=O)c3c(c4ccc(cc4[nH]3)O)C[C@@H](C(=O)NCC(=O)N1)NC(=O)[C@@H](NC(=O)[C@@H]5C[C@H](CN5C(=O)[C@@H](NC2=O)CC(=O)N)O)[C@@H](C)[C@H](C)O
Properties
C39H54N10O13S
Molar mass 902.97 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Toxicity

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Amatoxins selectively inhibit Eukaryotic RNA polymerase II by tightly to the enzyme and severely inhibits translocation along the DNA template; thus the synthesis of mRNA and proteins stops.[2] Amatoxin consumption is characterized by a long asymptomatic period of a few hours (up to a day or more) followed by quick physiological decline due to acute hepatic and tubular necrosis.[3] γ-Amanitin has been found to have similar levels of toxicity to other amatoxins such as α-Amanitin.

See also

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References

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  1. ^ PubChem. "Hazardous Substances Data Bank (HSDB) : 3460". pubchem.ncbi.nlm.nih.gov. Retrieved 2024-05-04.
  2. ^ de Mercoyrol, L.; Job, C.; Job, D. (1989-02-15). "Studies on the inhibition by alpha-amanitin of single-step addition reactions and productive RNA synthesis catalysed by wheat-germ RNA polymerase II". The Biochemical Journal. 258 (1): 165–169. doi:10.1042/bj2580165. ISSN 0264-6021. PMC 1138336. PMID 2467661.
  3. ^ Vetter, János (2023-08-07). "Amanitins: The Most Poisonous Molecules of the Fungal World". Molecules (Basel, Switzerland). 28 (15): 5932. doi:10.3390/molecules28155932. ISSN 1420-3049. PMC 10421264. PMID 37570902.
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