| Source: | Streptomyces
chartreusis |
| Synonyms | |
| Description: | Tunicamycin is a mixture of
homologous nucleoside antibiotics.
The main homologs differ in
the length of the fatty chain moiety. The following table defines
the four main Tunicamycin homologs.
Tunicamycin A, aka Tunicamycin V, n=9, mw=817
Tunicamycin B, aka Tunicamycin VII, n=10, mw=831
Tunicamycin C, aka Tunicamycin II, n=8, mw=845
Tunicamycin D, aka Tunicamycin X, n=11, mw=859
|
| CAS number: | 11089-65-9 |
| Merck index: | 14, 9819 |
| Molecular weight: | 844.4
(for n=10, "Tunicamycin VII") |
| Structure: |
 |
| Molecular Formula: | C39H64N4O16 (for
n=10, "Tunicamycin VII") |
| Canonical SMILES: |
CC(C)CCCCCCCCCCC=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
(for n=10, "Tunicamycin VII") |
Solubility
information: | Tunicamycin is soluble in DMSO, alkaline water, hot methanol
Practically insoluble in acetone,
ethyl acetate,
Unstable in acidic solutions |
| Specifications |
|
| Appearance: | White crystalline solid. |
| Purity: | At least 98% by TLC, HPLC |
λmax: | (In methanol) 205,260 |
| Melting point | Tunicamycin decomposes at 234°C - 235°C |
| Solubility | Clear solution at 50mg/ml of DMSO |
| Storage | -20°C. |
| Applications | Tunicamycins inhibit protein glycosylation. They arrest cell cycle in late G1
As Tunicamycin affects cell membrane permeability, it was
shown to increase production of antibiotics, such as streptomycin. (1) |
| Warnings | Tunicamycin is potentially harmful or fatal if swallowed,
inhaled, or absorbed through the skin. |
| Classification | nucleoside antibiotic
antiviral
proteins glucosylation inhibitor |
| Related products | |
| | For Research use only. Not for Human or Drug use
GMP/API grade available on request
No genetically modified organisms are used. |
| Publications |
|
| | Hirose-Kumagai
A, Yagita A, Tamura G, Akamatsu N.
Increase in streptomycin production caused by tunicamycin
The Journal of Antibiotics Vol.36 , No.10(1983)pp.1408-1410 |
| | Delom F, Emadali A, Cocolakis E, Lebrun JJ, Nantel A, Chevet E.
Calnexin-dependent regulation of tunicamycin-induced apoptosis in breast carcinoma MCF-7 cells.
Cell Death Differ. 2006 Jul 21 |
| | Horikawa K, Oishi N, Nakagawa J, Kasai A, Hayakawa K, Hiramatsu N, Takano Y, Yokouchi M, Yao J, Kitamura M.
Novel potential of tunicamycin as an activator of the aryl hydrocarbon receptor - dioxin responsive element signaling pathway.
FEBS Lett. 2006 Jun 26;580(15):3721-5. | |
|
