Amaninamide

In today's article we are going to delve into the topic of Amaninamide, exploring its implications, characteristics and possible applications. Amaninamide is a topic that has been the subject of interest and debate in various areas, generating conflicting opinions and challenging established concepts. Throughout this article, we will delve into the history of Amaninamide, analyze its relevance today, and examine its impact in different contexts. In addition, we will stop at the different perspectives that exist around Amaninamide, offering a panoramic view that allows us to understand the complexity of this topic. With a critical and enriching look, we will address the multiple facets of Amaninamide, with the aim of enriching knowledge and encouraging deep reflection on its meaning and significance.

Amaninamide
Names
Other names
4-(2-mercapto-L-tryptophan)-alpha-Amanitin
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C39H54N10O13S/c1-4-17(2)31-36(59)42-12-29(54)43-25-16-63(62)38-21(20-7-5-6-8-22(20)46-38)10-23(33(56)41-13-30(55)47-31)44-37(60)32(18(3)27(52)15-50)48-35(58)26-9-19(51)14-49(26)39(61)24(11-28(40)53)45-34(25)57/h5-8,17-19,23-27,31-32,46,50-52H,4,9-16H2,1-3H3,(H2,40,53)(H,41,56)(H,42,59)(H,43,54)(H,44,60)(H,45,57)(H,47,55)(H,48,58) checkY
    Key: BOHCOUQZNDPURZ-UHFFFAOYSA-N checkY
  • InChI=1/C39H54N10O13S/c1-4-17(2)31-36(59)42-12-29(54)43-25-16-63(62)38-21(20-7-5-6-8-22(20)46-38)10-23(33(56)41-13-30(55)47-31)44-37(60)32(18(3)27(52)15-50)48-35(58)26-9-19(51)14-49(26)39(61)24(11-28(40)53)45-34(25)57/h5-8,17-19,23-27,31-32,46,50-52H,4,9-16H2,1-3H3,(H2,40,53)(H,41,56)(H,42,59)(H,43,54)(H,44,60)(H,45,57)(H,47,55)(H,48,58)
    Key: BOHCOUQZNDPURZ-UHFFFAOYAZ
  • O=C(NCC(N(C(NCC(N(C3)C(N(CC(N)=O)C(N54C(O)C5)=O)=O)=O)=O)()(C)CC)=O)(CC1=C(S3=O)NC2=C1C=CC=C2)NC(((C)(O)CO)()N4=O)=O
Properties
C39H54N10O13S
Molar mass 902.97 g/mol
Appearance Colorless, crystalline solid
Soluble
Solubility in ethanol, methanol Soluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
checkY verify (what is checkY☒N ?)

Amaninamide is a cyclic peptide. It is one of the amatoxins, all of which are found in several members of the mushroom genera Amanita, Lepiota and Galerina. It differs from alpha-amanitin in lacking the hydroxyl group on tryptophan. This alters its UV absorption spectrum but not its toxicity.

Toxicology

Like other amatoxins, amaninamide is an inhibitor of RNA polymerase II. Upon ingestion, it binds to the RNA polymerase II enzyme which completely prevents mRNA synthesis, effectively causing cytolysis of hepatocytes (liver cells) and kidney cells.[1]

See also

References

  1. ^ M. Cochet-Meillhac; Chambon P. (1974). "Animal DNA-dependent RNA polymerases. 11. Mechanism of the inhibition of RNA polymerases B by amatoxins". Biochim Biophys Acta. 353 (2): 160–184. doi:10.1016/0005-2787(74)90182-8. PMID 4601749.