654380

Tunicamycin

from Strepomyces lysosuperficus, ≥98% (A+B+C+D, HPLC), powder, N-acetylglucosamine transferase, Calbiochem

• Synonym(s): Tunicamycin, Streptomyces lysosuperficus
• Empirical Formula (Hill Notation): C₃₉H₆₄N₄O₁₆
• CAS Number: 11089-65-9
• Molecular Weight: 844.94
• MDL number: MFCD00065709
• UNSPSC Code: 12352200
• NACRES: NA.77

Properties

• Product Name: Tunicamycin, Streptomyces lysosuperficus,
• description: Tunicamycin, Streptomyces lysosuperficus
• Quality Level: 200
• Assay: ≥98% (A+B+C+D, HPLC)
• form: powder
• manufacturer/tradename: Calbiochem^®
• solubility: DMSO: 10 mg/mL; DMF: soluble; pyridine: soluble
• shipped in: ambient
• storage temp.: 2-8°C
• SMILES string: N4(C=CC(=O)NC4=O)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C(O)C[C@H]2O[C@@H]([C@@H]([C@H]([C@H]2O)O)NC(=O)\C=C\CC(C)C)O[C@H]3O[C@@H]([C@H]([C@@H]([C@H]3NC(=O)C)O)O)CO
• InChI: 1S/C30H46N4O16/c1-11(2)5-4-6-16(38)32-19-23(43)20(40)14(47-29(19)50-28-18(31-12(3)36)22(42)21(41)15(10-35)48-28)9-13(37)26-24(44)25(45)27(49-26)34-8-7-17(39)33-30(34)46/h4,6-8,11,13-15,18-29,35,37,40-45H,5,9-10H2,1-3H3,(H,31,36)(H,32,38)(H,33,39,46)/b6-4+/t13?,14-,15-,18-,19-,20+,21-,22-,23-,24+,25-,26-,27-,28-,29-/m1/s1
• InChI key: ZHSGGJXRNHWHRS-PEALBESXSA-N

Description

General description

A nucleoside antibiotic that inhibits N-linked glycosylation and blocks the formation of N-glycosidic protein-carbohydrate linkages. Active in vitro against gram-positive bacteria, yeasts, fungi, and viruses. Inhibits the expression of functional thrombin receptors on human T-lymphoblastoid cells. Also inhibits thrombin-induced Ca²⁺ mobilization in cells.

Biochem/physiol Actions

Primary Target
N-linked glycosylation

Secondary Target
thrombin-induced Ca²⁺ mobilization in cells

Warning

Toxicity: Highly Toxic & Carcinogenic / Teratogenic (I)

Preparation Note

Aqueous solutions can be prepared from DMSO stock solutions by diluting in H₂O at pH 8.0 to 10.0 or with appropriate buffers at pH >7.0.

Reconstitution

Aqueous solutions can be prepared from stock solutions in DMSO by diluting with H₂O at pH 8.0 to 10.0 or with appropriate buffers at pH >7.0 (preferably >8.0).

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 2 weeks at -20°C.

Other Notes

Due to the nature of the Hazardous Materials in this shipment, additional shipping charges may be applied to your order. Certain sizes may be exempt from the additional hazardous materials shipping charges. Please contact your local sales office for more information regarding these charges.

Tordai, A., et al. 1995. Biochem. Biophys. Res. Commun. 206, 857.
Price, B.D., et al. 1992. J. Cell Physiol.152, 545.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety Information

• Pictograms: GHS06
• Signal Word: Danger
• Hazard Statements: H300
• Precautionary Statements: P264 - P270 - P301 + P310 - P405 - P501
• 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