Tunicamycin from Streptomyces sp.
SIGMA/T7765
CAS Number: 11089-65-9
MDL Number: MFCD00065709
Product Type: Chemical
antibiotic activity spectrum | fungi |
viruses | |
InChI | 1S/C37H60N4O16/c1-18(2)12 |
InChI key | YJQCOFNZVFGCAF-WPTOCQRYSA |
mode of action | protein synthesis | interferes |
Quality Level | 300 ![]() |
SMILES string | CC(C)CCCCCCCCC=CC(=O)N[ |
solubility | 95% ethanol: soluble 1 mg/mL, clear to faintly hazy |
acetone: insoluble | |
aqueous base: insoluble | |
chloroform: insoluble | |
dioxane: soluble <1 mg/mL | |
DMF: soluble >10 mg/mL | |
DMSO: soluble 4.9-5.1 mg/mL, clear to slightly hazy, colorless to yellow | |
ethyl acetate: insoluble | |
methanol: slightly soluble 4.9-5.1 mg/mL | |
methanol: soluble 4.9-5.1 mg/mL, clear to slightly hazy, colorless to yellow | |
pyridine: >10 mg/mL | |
THF: soluble <1 mg/mL | |
storage temp. | 2-8°C |
Application: | Tunicamycin has been used to study the effect of N-linked glycosylation of human proton-coupled folate transporter (HsPCFT) in HeLa cells. Tunicamycin has also been used to study the functional effects of coxsackievirus and adenovirus receptor (CAR) glycosylation in COS-7 cells. |
Biochem/physiol Actions: | Antibacterial and antifungal. Blocks the formation of protein N-glycosidic linkages by inhibiting the transfer of N-acetylglucosamine 1-phosphate to dolichol monophosphate. Inhibits bacterial and eukaryote N-acetylglucosamine transferases and prevents formation of N-acetylglucosamine lipid intermediates. |
General description: | Chemical structure: nucleoside |
General description: | Contains homologues A,B,C, and D. Composition may vary from lot to lot. Actual content given on label. |
Packaging: | 1, 5, 10, 50 mg in glass bottle |
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. |
Symbol | ![]() |
Signal word | Danger |
Hazard statements | H300 |
Precautionary statements | P264 - P270 - P301 + P310 - P405 - P501 |
Hazard Codes | T+ |
Risk Statements | 28 |
Safety Statements | 28-37/39-45 |
RIDADR | UN 3462 6.1 / PGII |
WGK Germany | WGK 3 |
Flash Point(F) | Not applicable |
Flash Point(C) | Not applicable |
Storage Temp. | 2-8°C |
UNSPSC | 12352200 |