Proamanullin

Promanullin is a cyclic nonribosomal peptide. It is an amatoxin, all of which are found in the mushroom genus Amanita.

Proamanullin
Names
Other names
2-L-Proline-3-isoleucine-alpha-amanitin
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C39H54N10O11S/c1-5-18(3)31-36(57)42-15-29(52)43-26-17-61(60)38-22(21-10-9-20(50)12-23(21)46-38)13-24(33(54)41-16-30(53)47-31)44-37(58)32(19(4)6-2)48-35(56)27-8-7-11-49(27)39(59)25(14-28(40)51)45-34(26)55/h9-10,12,18-19,24-27,31-32,46,50H,5-8,11,13-17H2,1-4H3,(H2,40,51)(H,41,54)(H,42,57)(H,43,52)(H,44,58)(H,45,55)(H,47,53)(H,48,56)/t18-,19-,24-,25-,26-,27-,31-,32-,61?/m0/s1 ☒N
    Key: CTYHFRWAIRSHQT-YRDOMICZSA-N ☒N
  • InChI=1/C39H54N10O11S/c1-5-18(3)31-36(57)42-15-29(52)43-26-17-61(60)38-22(21-10-9-20(50)12-23(21)46-38)13-24(33(54)41-16-30(53)47-31)44-37(58)32(19(4)6-2)48-35(56)27-8-7-11-49(27)39(59)25(14-28(40)51)45-34(26)55/h9-10,12,18-19,24-27,31-32,46,50H,5-8,11,13-17H2,1-4H3,(H2,40,51)(H,41,54)(H,42,57)(H,43,52)(H,44,58)(H,45,55)(H,47,53)(H,48,56)/t18-,19-,24-,25-,26-,27-,31-,32-,61?/m0/s1
    Key: CTYHFRWAIRSHQT-YRDOMICZBU
  • O=C(NCC(N[C@@](C(NCC(N[C@@H](C3)C(N[C@@H](CC(N)=O)C(N5[C@H]4CCC5)=O)=O)=O)=O)([H])[C@@H](C)CC)=O)[C@H](CC1=C(S3=O)NC2=C1C=CC(O)=C2)NC([C@@]([C@@H](C)CC)([H])N[C@@]4=O)=O
Properties
C39H54N10O11S
Molar mass 870.97 g/mol
Appearance Colorless, odorless
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Toxicology

Like other amatoxins, proamanullin is an inhibitor of RNA polymerase II. Promanullin has a specific attraction to the enzyme RNA polymerase II. Upon ingestion, it binds to the RNA polymerase II enzyme, effectively causing cytolysis of hepatocytes (liver cells).[1]

See also

References
  1. Cochet-Meilhac M, Chambon P (June 1974). "Animal DNA-dependent RNA polymerases. 11. Mechanism of the inhibition of RNA polymerases B by amatoxins". Biochim. Biophys. Acta. 353 (2): 160–84. doi:10.1016/0005-2787(74)90182-8. PMID 4601749.
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