Tunicamycin

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Tunicamycin
Tunicamycin.svg
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
11089-65-9 YesY
ChEMBL ChEMBL505513 N
Jmol-3D images Image
MeSH Tunicamycin
PubChem 6433557
Properties
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 isYesY/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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