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A9789

Sigma-Aldrich

Anisomycin

from Streptomyces griseolus, ≥98% (HPLC), solid, protein synthesis inhibitor

Synonym(s):

(2R,3S,4S)-2-(4-Methoxybenzyl)-3,4-pyrrolidinediol-3-acetate, 2-[(4-Methoxyphenyl)methyl]-3,4-pyrrolidinediol 3-acetate, Flagecidin

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About This Item

Empirical Formula (Hill Notation):
C14H19NO4
CAS Number:
22862-76-6
Molecular Weight:
265.30
Beilstein:
20705
EC Number:
245-269-7
MDL number:
MFCD00077650
UNSPSC Code:
12352200
PubChem Substance ID:
24891496
NACRES:
NA.77

Product Name

Anisomycin from Streptomyces griseolus, ≥98% (HPLC), solid

Quality Level

300

Assay

≥98% (HPLC)

form

solid

color

white to faint yellow

solubility

H2O: 2 mg/mL (Aqueous solutions are stable over a wide range of pH at room temperature.)
DMSO: 20 mg/mL
methanol: 20 mg/mL

antibiotic activity spectrum

neoplastics

Mode of action

protein synthesis | interferes

storage temp.

2-8°C

SMILES string

COc1ccc(C[C@H]2NC[C@H](O)[C@H]2OC(C)=O)cc1

InChI

1S/C14H19NO4/c1-9(16)19-14-12(15-8-13(14)17)7-10-3-5-11(18-2)6-4-10/h3-6,12-15,17H,7-8H2,1-2H3/t12-,13+,14+/m1/s1

InChI key

YKJYKKNCCRKFSL-RDBSUJKOSA-N

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Related Categories

Biochem/physiol Actions

Antibiotic isolated from Streptomyces griseolus that inhibits protein synthesis. Acts by inhibiting peptidyl transferase activity in eukaryote ribosomes.
Antibiotic isolated from Streptomyces griseolus that inhibits protein synthesis. Acts by inhibiting peptidyl transferase activity in eukaryote ribosomes. Reported to induce apoptosis in a variety of cells including promyelocytic leukemia cells, Jurkat cells, ventricular myocytes, and colon adenocarcinoma cells. Initiates intracellular signals and immediate early gene induction. Selective signaling agonist. Potent Jun-NH2 terminal kinase (JNK) agonist. Activates mitogen-activated protein (MAP) kinases (JNK/SAPK and p38/RK). Antiprotozoal agent.

Caution

Hygroscopic

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000417142
0000417142
0000407550
0000407550
0000382181

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J Daubriac et al.
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Puromycin reactivity does not accurately localize translation at the subcellular level
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eLife, 9, e60303-e60303 (2020)
Shuangxi Li et al.
Proceedings of the National Academy of Sciences of the United States of America, 117(40), 25104-25115 (2020-09-23)
Maintaining the fidelity of nascent peptide chain (NP) synthesis is essential for proteome integrity and cellular health. Ribosome-associated quality control (RQC) serves to resolve stalled translation, during which untemplated Ala/Thr residues are added C terminally to stalled peptide, as shown
Tao Ma et al.
Nature neuroscience, 16(9), 1299-1305 (2013-08-13)
Expression of long-lasting synaptic plasticity and long-term memory requires protein synthesis, which can be repressed by phosphorylation of eukaryotic initiation factor 2 α-subunit (eIF2α). Elevated phosphorylation of eIF2α has been observed in the brains of Alzheimer's disease patients and Alzheimer's
Margarita Cabrera et al.
Cell reports, 30(7), 2430-2443 (2020-02-23)
Cells have developed protein quality-control strategies to manage the accumulation of misfolded substrates during heat stress. Using a soluble reporter of misfolding in fission yeast, Rho1.C17R-GFP, we demonstrate that upon mild heat shock, the reporter collapses in protein aggregate centers
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