Tunicamycin
From Wikipedia, the free encyclopedia
| Tunicamycin | |
|---|---|
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| IUPAC 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 |
| Other names | NSC 177382 |
| Identifiers | |
| CAS number | [11089-65-9] |
| PubChem | |
| MeSH | |
| 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 |
| 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, 100 kPa) Infobox disclaimer and references |
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Tunicamycin is mixture of homologous nucleoside antibiotics that inhibits the enzyme GlcNAc phosphototransferase (GPT). GPT catalyzes the transfer of N-actelyglucosamine-1-phosphate from UDP-N-acetylglucosamine to dolichyl phosphate in the first step of glycoprotein synthesis. Tunicamycin blocks the synthesis of all N-linked glycoproteins (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 the bacterium Streptomyces Iysosuperficus.
[edit] See also
- Glycosylation - tunicamycin blocks all N-glycosylation of proteins
- Glycoprotein
- Streptomyces the genus
- the species Streptomyces clavuligerus produces a related molecule
[edit] References
[edit] External links
book section of Essentials in Glycobiology (1999) Tunicamycin: Inhibition of DOL-PP-GlcNAc Assembly- Tunicamycin data sheet prepared by a student of the Open University, UK
- Tunicamycin product details of the company Sigma Aldrich
