Store this product at 2–8 °C. When stored properly, the product remains active for at least 3 years. Solutions of tunicamycin in DMSO (5 mg/ml) can be stored at -20 °C in small aliquots of 25 - 50uL. No specific time frame for storage at -20 °C was indicated.
T7765
Tunicamycin
from Streptomyces sp., ≥98% (HPLC), powder, N-acetylglucosamine transferase inhibitor
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1 MG
$48.00
5 MG
$164.00
10 MG
$302.00
50 MG
$969.00
About This Item
CAS Number:
Beilstein/REAXYS Number:
6888090
MDL number:
UNSPSC Code:
51111800
PubChem Substance ID:
NACRES:
NA.77
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Product Name
Tunicamycin from Streptomyces sp.,
Quality Level
solubility
95% ethanol: soluble 1 mg/mL, clear to faintly hazy
THF: soluble <1 mg/mL
dioxane: soluble <1 mg/mL
DMF: soluble >10 mg/mL
pyridine: >10 mg/mL
DMSO: soluble 4.9-5.1 mg/mL, clear to slightly hazy, colorless to yellow
methanol: slightly soluble 4.9-5.1 mg/mL
methanol: soluble 4.9-5.1 mg/mL, clear to slightly hazy, colorless to yellow
acetone: insoluble
aqueous base: insoluble
chloroform: insoluble
ethyl acetate: insoluble
antibiotic activity spectrum
fungi
viruses
mode of action
protein synthesis | interferes
storage temp.
2-8°C
SMILES string
CC(C)CCCCCCCC\C=C\C(=O)N[C@@H]1[C@@H](O)[C@@H](O)[C@@H](C[C@@H](O)[C@H]2O[C@H]([C@H](O)[C@@H]2O)N3C=CC(=O)NC3=O)O[C@H]1O[C@@H]4O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]4NC(C)=O
InChI
1S/C37H60N4O16/c1-18(2)12-10-8-6-4-5-7-9-11-13-23(45)39-26-30(50)27(47)21(54-36(26)57-35-25(38-19(3)43)29(49)28(48)22(17-42)55-35)16-20(44)33-31(51)32(52)34(56-33)41-15-14-24(46)40-37(41)53/h11,13-15,18,20-22,25-36,42,44,47-52H,4-10,12,16-17H2,1-3H3,(H,38,43)(H,39,45)(H,40,46,53)/b13-11+/t20-,21-,22+,25+,26-,27+,28+,29+,30-,31+,32-,33-,34-,35+,36+/m1/s1
InChI key
YJQCOFNZVFGCAF-WPTOCQRYSA-N
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This Item | 654380 | T4540 | 647925 |
|---|---|---|---|
| Quality Level 300 | Quality Level 200 | Quality Level 200 | Quality Level 100 |
| storage temp. 2-8°C | storage temp. 2-8°C | storage temp. −20°C | storage temp. −20°C |
| solubility 95% ethanol: soluble 1 mg/mL, clear to faintly hazy, dioxane: soluble <1 mg/mL, pyridine: >10 mg/mL, methanol: slightly soluble 4.9-5.1 mg/mL, acetone: insoluble, chloroform: insoluble, THF: soluble <1 mg/mL, DMSO: soluble 4.9-5.1 mg/mL, clear to slightly hazy, colorless to yellow, aqueous base: insoluble, DMF: soluble >10 mg/mL, ethyl acetate: insoluble, methanol: soluble 4.9-5.1 mg/mL, clear to slightly hazy, colorless to yellow | solubility DMSO: 10 mg/mL, DMF: soluble, pyridine: soluble | solubility methanol: soluble 4.90-5.10 mg/mL, clear (Pale yellow to yellow), methanol: soluble 4.90-5.10 mg/mL, clear, pale yellow to yellow | solubility ethanol: 1 mg/mL, DMSO: 20 mg/mL, methanol: soluble |
| antibiotic activity spectrum fungi | antibiotic activity spectrum - | antibiotic activity spectrum - | antibiotic activity spectrum - |
| mode of action protein synthesis | interferes | mode of action - | mode of action enzyme | inhibits | mode of action - |
General description
Chemical structure: nucleoside
Contains homologues A,B,C, and D. Composition may vary from lot to lot. Actual content given on label.
Tunicamycin is an antibiotic and a glycosylation inhibitor. Its mode of action includes blocking human UDP-HexNAc:polyprenol-P HexNAc-1-P enzymes in the enzyme GlcNAc phosphotransferase (GPT). Glycosylation is a major post-translational modification that plays a critical role in glycoprotein folding, stability, and subcellular localization, as well as in the biological functions of the glycoprotein. Abnormal glycosylation has been identified as a signature of cancer and has been shown to play a significant role in tumor progression, metastasis, and chemoresistance. Research shows tunicamycin exhibits antitumor action. Furthermore, tunicamycin inhibition of N-glycosylation ultimately results in the build-up of unstructured proteins in the endoplasmic reticulum (ER) lumen, potentially leading to ER stress.[1] Tunicamycin also exhibits antibacterial and antifungal actions. It blocks the formation of protein N-glycosidic linkages by inhibiting the transfer of N-acetylglucosamine 1-phosphate to dolichol monophosphate. Tunicamycin also Inhibits bacterial and eukaryote N-acetylglucosamine transferases and prevents the formation of N-acetylglucosamine lipid intermediates.
Application
Tunicamycin has been used to study the effect of N-linked glycosylation of human proton-coupled folate transporter (HsPCFT) in HeLa cells[2]. Tunicamycin has also been used to study the functional effects of coxsackievirus and adenovirus receptor (CAR) glycosylation in COS-7 cells[3]. Tunicamycin from Streptomyces sp. has been used to inhibit N-glycosylation in cell culture experiments.
Biochem/physiol Actions
Blocks the formation of protein N-glycosidic linkages.
Preparation Note
Tunicamycin dissolves in DMSO at 4.9-5.1 mg/ml and yields a clear to very slightly hazy, colorless to yellow solution. Furthermore, tunicamycin is soluble in DMF (>10 mg/ml), pyridine (>10 mg/ml), water (<5 mg/ml, pH 9.0), dioxane (<1 mg/ml) and THF. However, it is insoluble in other organic solvents such as acetone, chloroform, and ethyl acetate, and in aqueous solutions with pH <6. Aqueous solutions can be prepared from stock solutions by diluting with water at pH 8-10 or with buffers with pH >7, preferably >8. Tunicamycin will not dissolve in phosphate buffer, pH 8, at 1 mg/ml, even with heating, but solubility can be achieved by raising the pH to 9 and back titrating to pH 7-8.
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 1 Oral
Storage Class
6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Is it possible to store the product at -20/30°C for extended storage?
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What is the molecular weight for T7765 product ?
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The molecular weight of the product is lot-specific. Each homolog has a specific molecular weight: A = 817, B = 831, C = 845, and D = 859. The lot-specific Certificate of Analysis (COA) provides the percentage contribution for each homolog.
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