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Merck

S1442

Sigma-Aldrich

Sordarin sodium salt

from Sordaria araneosa, ≥98% (HPLC), solid

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About This Item

Fórmula empírica (notación de Hill):
C27H39NaO8
Número de CAS:
Peso molecular:
514.58
MDL number:
UNSPSC Code:
51111800
PubChem Substance ID:
NACRES:
NA.77

biological source

Sordaria araneosa

Quality Level

assay

≥98% (HPLC)

form

solid

solubility

H2O: soluble ≤10 mg/mL

antibiotic activity spectrum

fungi

mode of action

protein synthesis | interferes

shipped in

wet ice

storage temp.

−20°C

SMILES string

[Na+].[H]C(=O)[C@]12C[C@]3([H])C=C(C(C)C)[C@@]1(C([O-])=O)[C@]3(CO[C@@H]4O[C@H](C)[C@@H](OC)[C@@H](O)[C@@H]4O)C[C@]5([H])[C@H](C)CC[C@@]25[H]

InChI

1S/C27H40O8.Na/c1-13(2)19-8-16-9-25(11-28)18-7-6-14(3)17(18)10-26(16,27(19,25)24(31)32)12-34-23-21(30)20(29)22(33-5)15(4)35-23;/h8,11,13-18,20-23,29-30H,6-7,9-10,12H2,1-5H3,(H,31,32);/q;+1/p-1/t14-,15-,16+,17-,18-,20+,21+,22-,23-,25+,26+,27+;/m1./s1

InChI key

ILUKWKGTAAZHDW-IGICPMPSSA-M

Application

Soradrin sodium salt has been used as an antifungal compound to treat mycelia for immunofluorescence microscopy studies. It may be used in in vitro diphtheria toxin sensitivity assays.

Biochem/physiol Actions

Sordarin is an antifungal metabolite possessing a tetracyclic diterpene glycoside structure. It is a highly potent inhibitor of eukaryotic protein synthesis with selectivity for the fungal translation machinery. The elongation factor EF-2 is the molecular target for sordarin. It blocks ribosomal translocation by stabilizing the EF2-ribosome complex in a manner similar to that of fusidic acid in the bacterial system. Additional cellular components (including rpP0, which is an essential protein of the ribosomal large subunit stalk) are involved in its mechanism of action. Sordarin inhibits in vitro translation in the pathogenic fungi C. albicans, C. glabrata, and C. neoformans. In addition to its therapeutic potential, sordarin is a useful tool for the analysis of protein translation events.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Wael Abdel-Fattah et al.
Toxins, 5(5), 958-968 (2013-05-07)
Diphtheria toxin (DT) inhibits eukaryotic translation elongation factor 2 (eEF2) by ADP-ribosylation in a fashion that requires diphthamide, a modified histidine residue on eEF2. In budding yeast, diphthamide formation involves seven genes, DPH1-DPH7. In an effort to further study diphthamide

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