A RNA polymerase II and III inhibitor
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β-Amanitin

Item No. 18142

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-L-aspartic acid-α-amanitin
CAS Number
21150-22-1
Molecular Formula
C39H53N9O15S
Formula Weight
920.0
Purity
≥90%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
Water: 1 mg/ml
SMILES
O=C(N[C@@]1([H])[C@@H](C)[C@@H](O)CO)[C@@]2([H])N(C[C@H](O)C2)C([C@H](CC(O)=O)NC([C@@]([H])(NC(CNC([C@@]([C@H](CC)C)([H])NC(CN3)=O)=O)=O)CS(C4=C(C(C=CC(O)=C5)=C5N4)C[C@@H](C3=O)NC1=O)=O)=O)=O
InChi Code
InChI=1S/C39H53N9O15S/c1-4-16(2)31-36(60)41-11-28(53)42-25-15-64(63)38-21(20-6-5-18(50)7-22(20)45-38)9-23(33(57)40-12-29(54)46-31)43-37(61)32(17(3)27(52)14-49)47-35(59)26-8-19(51)13-48(26)39(62)24(10-30(55)56)44-34(25)58/h5-7,16-17,19,23-27,31-32,45,49-52H,4,8-15H2,1-3H3,(H,40,57)(H,41,60)(H,42,53)(H,43,61)(H,44,58)(H,46,54)(H,47,59)(H,55,56)/t16-,17-,19+,23-,24-,25-,26-,27-,31-,32-,64?/m0/s1
InChi Key
IEQCUEXVAPAFMQ-JAXJKTSHSA-N
Origin
Fungus/Amanita phalloides
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $266

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    Product Description

    β-Amanitin is a cyclic peptide found in several species of the Amanita genus, as well as other poisonous fungi.1 It inhibits RNA polymerase II and III but not RNA polymerase I or bacterial RNA polymerase, thus preventing mammalian protein synthesis.2,3 The biological activity of this toxin is similar to that of α-amanitin (Item No. 17898) but differs structurally by the presence of a carboxyl group, which is useful for coupling reactions.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Walton, J.D., Hallen-Adams, H.E., and Luo, H. Ribosomal biosynthesis of the cyclic peptide toxins of Amanita mushrooms. Biopolymers 94(5), 659-664 (2010).

    2. Gu, W., Powell, W., Mote, J., Jr., et al. Nascent RNA cleavage by arrested RNA polymerase II does not require upstream translocation of the elongation complex on DNA. The Journal of Biological Chemisty 268(34), 25604-25616 (1993).

    3. Tipper, D.J. Inhibition of yeast ribonucleic acid polymerases by thiolutin. J. Bacteriol. 116(1), 245-256 (1973).

    4. Anderl, J., Echner, H., and Faulstich, H. Chemical modification allows phallotoxins and amatoxins to be used as tools in cell biology. Beilstein J. Org. Chem. 8, 2072-2084 (2012).