An antimicrobial and inhibitor of glycosylation
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Tunicamycin Mixture

Item No. 11445

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
CAS Number
11089-65-9
Molecular Formula
C39H64N4O16 (for Tunicamycin VII)
Formula Weight
845.0
Purity
≥95% (mixture of congeners)
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/mlDMSO:PBS(pH 7.2) (1:3): 0.25 mg/ml
λmax
208, 260 nm
SMILES
O=C1C=CN([C@@H]2O[C@H]([C@H](O)C[C@H]3O[C@@H](O[C@@H]4[C@H](NC(C)=O)[C@@H](O)[C@H](O)[C@@H](CO)O4)[C@H](NC(/C=C/CCCCCCCCCCC(C)C)=O)[C@@H](O)[C@H]3O)[C@@H](O)[C@H]2O)C(N1)=O
InChi Code
InChI=1S/C39H64N4O16/c1-20(2)14-12-10-8-6-4-5-7-9-11-13-15-25(47)41-28-32(52)29(49)23(56-38(28)59-37-27(40-21(3)45)31(51)30(50)24(19-44)57-37)18-22(46)35-33(53)34(54)36(58-35)43-17-16-26(48)42-39(43)55/h13,15-17,20,22-24,27-38,44,46,49-54H,4-12,14,18-19H2,1-3H3,(H,40,45)(H,41,47)(H,42,48,55)/b15-13+/t22-,23-,24-,27-,28-,29+,30-,31-,32-,33+,34-,35-,36-,37-,38+/m1/s1
InChi Key
ZOCXUHJGZXXIGQ-NPXWYGMKSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Tunicamycin mixture is a mixture of tunicamycins with variable trans-2,3-unsaturated branched chain fatty acid (BFCA) chain lengths. Tunicamycins are anti-microbial agents that are active against Gram-positive bacteria, fungi, and viruses.1 They inhibit the N-acetylhexosamine (HexNAc) phosphotransferase family of enzymes in bacteria and prevent peptidoglycan biosynthesis.2 In eukaryotes, they inhibit N-acetylglucosamine (GlcNAc) phosphotransferase (GPT), preventing the first step in N-linked glycosylation and inducing the unfolded protein response and cell death.2,3,4 The cellular toxicity of tunicamycins is linked to the trans-2,3-unsaturated BCFA, and saturated BCFA-containing tunicamycin derivatives, such as TunR1 (Item No. 31537) and TunR2 (Item No. 31538), have reduced toxicity.2,5 Tunicamycins impair glycosylation of the receptor tyrosine kinases EGFR, HER2, HER3, and IGF-1R, which prevents their translocation out of the endoplasmic reticulum and Golgi apparatus and reduces their protein levels and activity.6 Tunicamycin sensitizes EGFR inhibitor-resistant U251 glioma and Bx/PC-3 pancreatic adenocarcinoma cells to irradiation.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Takatsuki, A., Arima, K., and Tamura, G. Tunicamycin, a new antibiotic. I. Isolation and characterization of tunicamycin. J. Antibiot. (Tokyo) 24(4), 215-223 (1971).

    2. Price, N.P., Hartman, T.M., Li, J., et al. Modified tunicamycins with reduced eukaryotic toxicity that enhance the antibacterial activity of β-lactams. J. Antibiot. (Tokyo) 70(11), 1070-1077 (2017).

    3. Tkacz, J.S., and Lampen, O. Tunicamycin inhibition of polyisoprenyl N-acetylglucosaminyl pyrophosphate formation in calf-liver microsomes. Biochem. Biophys. Res. Commun. 65(1), 248-257 (1975).

    4. Berger, E.G., Buddecke, E., Kamerling, J.P., et al. Structure, biosynthesis and functions of glycoprotein glycans. Experientia 38(10), 1129-1162 (1982).

    5. Price, N.P.J., Jackson, M.A., Hartman, T.M., et al. Branched chain lipid metabolism as a determinant of the N-Acyl variation of Streptomyces natural products. ACS Chem. Biol. 16(1), 116-124 (2021).

    6. Contessa, J.N., Bhojani, M.S., Freeze, H.H., et al. Inhibition of N-linked glycosylation disrupts receptor tyrosine kinase signaling in tumor cells. Cancer Res. 68(10), 3803-3809 (2008).

    Product Citations

    Esposito, M., Mondal, N., Greco, T.M., et al. Bone vascular niche E-selectin induces mesenchymal-epithelial transition and Wnt activation in cancer cells to promote bone metastasis. Nat. Cell. Biol. (2019).

    Okuda, K., and Silverman, N. Drosophila model of Leishmania amazonensis infection. Bio. Protoc. 7(23), e2640 (2017).

    Bosnakovski, D., Choi, S.H., Strasser, J.M., et al. High-throughput screening identifies inhibitors of DUX4-induced myoblast toxicity. Skelet. Muscle 4(4), (2014).