(E)-N-[(2S,3R,4R,5R,6R)-2-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[2-[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl]-4,5-dihydroxyoxan-3-yl]-5-methylhex-2-enamide

Base Information

• Chemical Name: (E)-N-[(2S,3R,4R,5R,6R)-2-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[2-[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl]-4,5-dihydroxyoxan-3-yl]-5-methylhex-2-enamide
• CAS No.: 11089-65-9
• Deprecated CAS: 11118-26-6
• Molecular Formula: C37H60N4O16
• Molecular Weight: 816.89
• Hs Code.: 29419090
• Mol file: 11089-65-9.mol

Synonyms:NSC 177382;UNII-55W4525Q2E;C38H62N4O16;55W4525Q2E;(E)-N-[(2S,3R,4R,5R,6R)-2-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[2-[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl]-4,5-dihydroxyoxan-3-yl]-5-methylhex-2-enamide;LS-158209;Q3542091

Chemical Property of (E)-N-[(2S,3R,4R,5R,6R)-2-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[2-[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl]-4,5-dihydroxyoxan-3-yl]-5-methylhex-2-enamide

Chemical Property:

• Appearance/Colour: White crystalline solid.
• Melting Point: 234-235℃ (decomposition)
• Refractive Index: 1.649
• Flash Point: 87℃
• PSA: 311.82000
• Density: 1.57g/cm³
• LogP: -2.08660
• Storage Temp.: 2-8°C
• Sensitive.: Moisture & Light Sensitive
• Solubility.: Soluble in methanol, ethanol, DMSO, or DMF
• XLogP3: -4.1
• Hydrogen Bond Donor Count: 11
• Hydrogen Bond Acceptor Count: 16
• Rotatable Bond Count: 12
• Exact Mass: 718.29088139
• Heavy Atom Count: 50
• Complexity: 1290

Purity/Quality:

98%,99%, ^*data from raw suppliers

Tunicamycin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+,T
• Hazard Codes: T+,T
• Statements: 28
• Safety Statements: 28-37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)CC=CC(=O)NC1C(C(C(OC1OC2C(C(C(C(O2)CO)O)O)NC(=O)C)CC(C3C(C(C(O3)N4C=CC(=O)NC4=O)O)O)O)O)O
• Isomeric SMILES: CC(C)C/C=C/C(=O)N[C@@H]1[C@H]([C@H]([C@H](O[C@H]1O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)NC(=O)C)CC([C@@H]3[C@H]([C@H]([C@@H](O3)N4C=CC(=O)NC4=O)O)O)O)O)O
• 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. They inhibit the N-acetylhexosamine (HexNAc) phosphotransferase family of enzymes in bacteria and prevent peptidoglycan biosynthesis. 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. The cellular toxicity of tunicamycins is linked to the trans-2,3-unsaturated BCFA, and saturated BCFA-containing tunicamycin derivatives, such as TunR1 and TunR2 , have reduced toxicity. 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. Tunicamycin sensitizes EGFR inhibitor-resistant U251 glioma and Bx/PC-3 pancreatic adenocarcinoma cells to irradiation.
• Uses: The tunicamycins are a family of lipophilic nucleosides with fatty acids conjugated to an aminoglycoside group. The complex comprises analogues, tunicamycins I to X. This composition is typical of other products less precisely described as tunicamycins A to D. The tunicamycins act by blocking the formation of N-glycoside linkages to proteins via inhibition of formation of dolichol monophosphate from N-acetylglucosamine-1-phosphate. Tunicamycin blocks the synthesis of all N-linked glycoproteins (N-glycans) and causes cell cycle arrest in G1 phase. Tunicamycins are broadly active against prokaryotes, eukaryotes and viruses. As a tool in studying glycoproteins in a wide variety of biological systems. Tunicamycin has been widely used in the study of glycoprotein synthesis in various biological systems. During protein glycosylation, tunicamycin is noted to be an inhibitor of the transfer of saccharide moieties to dolichol during dolichol-linked glycoprotein synthesis. Dose-dependent inhibition of DNA synthesis may be related to the alteration of glycoproteins, which thereby affects the transport of thymidine into cells. Additionally, tunicamycin has been reported to prevent cell cycle progression in primary cultures of rat glial cells, as well as inhibit lipid-mediated protein glycosylation in chick or mouse fibroblasts in a dose-dependent manner.