Tunicamycin

Tunicamycin

Names
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 Registry Number	11089-65-9 Y
ChEMBL	ChEMBL505513 N
Jmol-3D images	Image
MeSH	Tunicamycin
PubChem	6433557
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
Properties
Chemical formula	C39H64N4O16
Molar mass	N/A
Hazards
R-phrases	28
S-phrases	28-37/39-45
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N verify (what is: Y/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]

See also

• Glycosylation - tunicamycin blocks all N-glycosylation of proteins
• Glycoprotein
• Streptomyces the genus

References

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