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T7765

Sigma-Aldrich

Tunicamycin from Streptomyces sp.

CAS Number:
Beilstein:
6888090
MDL number:
PubChem Substance ID:
NACRES:
NA.77

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

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

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General description

Chemical structure: nucleoside
Contains homologues A,B,C, and D. Composition may vary from lot to lot. Actual content given on label.

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.

Packaging

1, 5, 10, 50 mg in glass bottle

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.

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.

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 1 Oral

Storage Class Code

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Certificate of Origin

Product Information Sheet

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