Tunicamycin Properties, Molecular Formula, Applications - WorldOfChemicals

Tunicamycin Properties

Tunicamycin

Molecule Structure Image

Description

 

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 and causes cell cycle arrest in G1 phase. It is used as an experimental tool in biology, e.g. to induce unfolded protein response. It is produced by several bacteria, including Streptomyces clavuligerus and Streptomyces Iysosuperficus.

Chemical Properties

Appearance White Crystalline Solid
CAS Number 11089-65-9
Density 1.57 g/cm3
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
InChI 1S/C39H64N4O16/c1-20(2)14-12-10-8-6-4-5-7-9-11-13-15-25(47)41-28-32(52)29(49)23(56-38(28)59-37-27(40-21(3)45)31(51)30(50)24(19-44)57-37)18-22(46)35-33(53)34(54)36(58-35)43-17-16-26(48)42-39(43)55/h13,15-17,20,22-24,27-38,44,46,49-54H,4-12,14,18-19H2,1-3H3,(H,40,45)(H,41,47)(H,42,48,55)/b15-13+/t22-,23-,24-,27-,28-,29+,30-,31-,32-,33+,34-,35-,36-,37?,38+/m1/s1
InChIKey ZOCXUHJGZXXIGQ-SQXRCPDGSA-N
Melting Point 234-235 °C
Molar Mass 844.9468 g/mol
Molecular Formula C39H64N4O16
RTECS Number YO7980200
Synonyms Tunicamycin Streptomyces sp.;NSC 177382;Tunicamycin