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