Tunicamycin

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Tunicamycin
Tunicamycin.svg
Identifiers
CAS number 11089-65-9 YesY
PubChem 6433557
MeSH Tunicamycin
ChEMBL CHEMBL505513 N
Jmol-3D images {{#if: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|Image 1

Properties
Molecular formula C39H64N4O16
Molar mass N/A
Hazards
R-phrases 28
S-phrases 28-37/39-45
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

Tunicamycin is a mixture of homologous nucleoside antibiotics that inhibits the UDP-HexNAc: polyprenol-P HexNAc-1-P family of enzymes. In eukaryotes, this includes the enzyme GlcNAc phosphotransferase (GPT), which catalyzes the transfer of N-acetylglucosamine-1-phosphate from UDP-N-acetylglucosamine to dolichol phosphate in the first step of glycoprotein synthesis. Tunicamycin blocks N-linked glycosylation (N-glycans) and causes cell cycle arrest in G1 phase. It is used as an experimental tool in biology, e.g. to induce unfolded protein response.[1] Tunicamycin is produced by several bacteria, including Streptomyces clavuligerus and Streptomyces lysosuperficus.

Tunicamycin homologues have varying molecular weights owing to the variability in fatty acids side chain conjugates.[2]

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