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T7765 Sigma-Aldrich

Tunicamycin from Streptomyces sp.

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Properties

Related Categories AIDS and Viral Research Reagents, Antibacterial, Antibiotics, Antibiotics A to Z, Antibiotics T-Z,
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

Description

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.

Safety & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
UN 3462 6.1 / PGII
WGK Germany 
WGK 3
RTECS 
YO7980200
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

Discover Bioactive Small Molecules for Immunology Research

The immune system is a complex network to detect and defend against non-self pathogenic agents, such as disease-causing viruses, bacteria, and other microorganisms. Various signaling pathways contrib...
Keywords: Antibiotics, Antifungals, Antivirals, Apoptosis, Bioactive small molecules, Cell signaling, Diabetes, Diseases, Immunology, Inflammation

Inhibition of Cell Wall Biosynthesis by Antibiotics

Antibiotics are molecules that specifically target and kill cells. The term antibiotic is frequently used interchangeably with the word antibacterial, but antiviral, antifungal and antineoplastic com...
BioFiles 2006, 1.4, 7.
Keywords: Antibiotics, Antifungals, Antivirals, Building blocks, Glycosylations, Metabolism

Peer-Reviewed Papers
15

References

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