Tunicamycin from Streptomyces sp.

SIGMA/T7765

CAS Number: 11089-65-9
MDL Number: MFCD00065709
Product Type: Chemical

Catalog Number	PKG Qty.	Price


45-T7765-1MG	1 mg	$48.00 1/EA	Add To Favorites
45-T7765-5MG	5 mg	$164.00 1/EA	Add To Favorites
45-T7765-10MG	10 mg	$302.00 1/EA	Add To Favorites
45-T7765-50MG	50 mg	$969.00 1/EA	Add To Favorites

This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: T7765-10MG

Properties
Descriptions
Safety Info.
Basic Data

antibiotic activity spectrum	fungi
	viruses
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
mode of action	protein synthesis \| interferes
Quality Level	300
SMILES string	CC(C)CCCCCCCCC=CC(=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
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. 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.
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.
General description:	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. 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.
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	GHS06
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	51111800

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