Tunicamycin from Streptomyces sp.
CAS Number: | 11089-65-9 |
Beilstein/REAXYS Number: | 6888090 |
MDL number: | MFCD00065709 |
PubChem Substance ID: | 57654701 |
NACRES: | NA.77 |
Кат. номер |
T7765-10MG-PW |
T7765-1MG-PW |
T7765-50MG-PW |
T7765-5MG |
T7765-10MG |
T7765-1MG |
T7765-50MG |
T7765-5MG-PW |
Chemical structure: nucleoside
Contains homologues A,B,C, and D. Composition may vary from lot to lot. Actual content given on label.
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.
1, 5, 10, 50 mg in glass bottle
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.
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.
Quality Level | 300, |
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 |
Mode of action | protein synthesis | interferes |
antibiotic activity spectrum | fungi, viruses |
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 |
pictograms | GHS06 |
signalword | Danger |
hcodes | H300 |
pcodes | P264 - P270 - P301 + P310 - P405 - P501 |
Personal Protective Equipment | Eyeshields,, Faceshields,, Gloves,, type P1 (EN143) respirator filter,, type P3 (EN 143) respirator cartridges, |
RIDADR | UN 3462 6.1 / PGII |
WGK Germany | WGK 3 |
Flash Point F | Not applicable |
Flash Point C | Not applicable |