Tunicamycin

Tunicamycin: Tunicamycin

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^Y

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

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

Molecular formula C₃₉H₆₄N₄O₁₆

Molar mass 840.0 g/mol

Hazards

R-phrases 28

S-phrases 28-37/39-45

N (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Tunicamycin is 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-actelyglucosamine-1-phosphate from UDP-N-acetylglucosamine to dolichol 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 several bacteria, including Streptomyces clavuligerus and Streptomyces Iysosuperficus.

See also

Glycosylation - tunicamycin blocks all N-glycosylation of proteins

Glycoprotein

Streptomyces the genus

References

^ Hepatitis C virus envelope proteins regulate CHOP via induction of ...

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

Categories:
Antibiotics

Tunicamycin

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^Y
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
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
Molecular formula	C₃₉H₆₄N₄O₁₆
Molar mass	840.0 g/mol
Hazards
R-phrases	28
S-phrases	28-37/39-45
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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Look at other dictionaries:

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Tunicamycin

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