Tunicamycin, Protein glycosylation inhibitor

Key facts

CAS number

66081-37-6

Purity

> 98%

Form

Solid

Source

Streptomyces sp.

Molecular weight

816.9 Da

Molecular formula

C₃₇H₆₀N₄O₁₆

PubChem identifier

16220051

Nature

Native

Solubility

Soluble in DMSO to 50 mM.

Biochemical name

Tunicamycin Ready Made Solution

Biological description

Nucleoside antibiotic that inhibits protein glycosylation. Inhibits GlcNAc phosphotransferase (GPT) and inhibits the transfer of N-acetylglucosamine-1-phosphate from UDP-N-acetylglucosamine to dolichol phosphate in the first step of glycoprotein synthesis. Inhibits N-linked glycosylation and blocks the formation of N-glycosidic protein-carbohydrate linkages. Active in vitro against Gram-positive bacteria, yeasts, fungi and viruses.

Canonical SMILES

CC(C)CCCCCCCCC=CC(=O)NC1C(C(C(OC1OC2C(C(C(C(O2)CO)O)O)NC(=O)C)CC(C3C(C(C(O3)N4C=CC(=O)NC4=O)O)O)O)O)O

Isomeric SMILES

CC(C)CCCCCCCC/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)C[C@H]([C@@H]3[C@H]([C@H]([C@@H](O3)N4C=CC(=O)NC4=O)O)O)O)O)O

InChI

InChI=1S/C37H60N4O16/c1-18(2)12-10-8-6-4-5-7-9-11-13-23(45)39-26-30(50)27(47)21(54-36(26)57-35-25(38-19(3)43)29(49)28(48)22(17-42)55-35)16-20(44)33-31(51)32(52)34(56-33)41-15-14-24(46)40-37(41)53/h11,13-15,18,20-22,25-36,42,44,47-52H,4-10,12,16-17H2,1-3H3,(H,38,43)(H,39,45)(H,40,46,53)/b13-11+/t20-,21-,22+,25+,26-,27+,28+,29+,30-,31+,32-,33-,34-,35+,36+/m1/s1

InChIKey

YJQCOFNZVFGCAF-WPTOCQRYSA-N

IUPAC name

(E)-N-[(2S,3R,4R,5R,6R)-2-[(2S,3S,4S,5R,6S)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[(2R)-2-[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl]-4,5-dihydroxyoxan-3-yl]-12-methyltridec-2-enamide