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Merck
CN

SML1287

Sigma-Aldrich

Tunicamycin

from Streptomyces sp., ≥98% (HPLC), DMSO solution, N-acetylglucosamine transferase inhibitor

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About This Item

经验公式(希尔记法):
C37H60N4O16
CAS号:
分子量:
816.89
EC 号:
UNSPSC代码:
51111800
NACRES:
NA.77

产品名称

Tunicamycin Ready Made Solution, 5 mg/mL in DMSO, from Streptomyces sp.

生物来源

Streptomyces sp.

质量水平

表单

DMSO solution

浓度

5 mg/mL in DMSO

储存温度

2-8°C

SMILES字符串

N4(C=CC(=O)NC4=O)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C(O)C[C@H]2O[C@@H]([C@@H]([C@H]([C@H]2O)O)NC(=O)\C=C\CC(C)C)O[C@H]3O[C@@H]([C@H]([C@@H]([C@H]3NC(=O)C)O)O)CO

InChI

1S/C30H46N4O16/c1-11(2)5-4-6-16(38)32-19-23(43)20(40)14(47-29(19)50-28-18(31-12(3)36)22(42)21(41)15(10-35)48-28)9-13(37)26-24(44)25(45)27(49-26)34-8-7-17(39)33-30(34)46/h4,6-8,11,13-15,18-29,35,37,40-45H,5,9-10H2,1-3H3,(H,31,36)(H,32,38)(H,33,39,46)/b6-4+/t13?,14-,15-,18-,19-,20+,21-,22-,23-,24+,25-,26-,27-,28-,29-/m1/s1

InChI key

ZHSGGJXRNHWHRS-PEALBESXSA-N

一般描述

Tunicamycin Ready Made Solution contains homologues A,B,C, and D. The composition may vary from lot to lot. Actual content given on label.
Tunicamycin was first isolated from Streptomyces lysosuperificus based on its antiviral activity. It contains N-acetylglucosamine and inhibits glycoprotein biosynthesis, including virus membrane glycoproteins.

应用

Tunicamycin has been used to study the effect of N-linked glycosylation of human proton-coupled folate transporter (HsPCFT) in HeLa cells. Tunicamycin has also been used to study the functional effects of coxsackievirus and adenovirus receptor (CAR) glycosylation in COS-7 cells.

生化/生理作用

Tunicamycin is an antibacterial and antifungal.
Tunicamycin is an antibacterial and antifungal. Tunicamycin blocks the formation of protein N-glycosidic linkages by inhibiting the transfer of N-acetylglucosamine 1-phosphate to dolichol monophosphate. Tunicamycin inhibits bacterial and eukaryote N-acetylglucosamine transferases and prevents formation of N-acetylglucosamine lipid intermediates.
Tunicamycin plays an important role in the antitumor activity of trastuzumab on breast cancer in vitro and in vivo. In human cell lines, tunicamycin enhances cytotoxicity stimulated by cisplatin. It prevents angiogenesis in nude mice by reducing the expression of vascular endothelial growth factor (VEGF).

储存分类代码

10 - Combustible liquids

WGK

WGK 1

闪点(°F)

188.6 °F

闪点(°C)

87 °C

法规信息

新产品

历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

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The specific site of tunicamycin inhibition in the formation of dolichol-bound N-acetylglucosamine derivatives.
L Lehle et al.
FEBS letters, 72(1), 167-170 (1976-11-15)
Tunicamycin enhances the antitumor activity of trastuzumab on breast cancer in vitro and in vivo.
Han X, et al.
Oncotarget, 6(36), 38912?38925-38912?38925 (2015)
Sjors M Kas et al.
Scientific reports, 13(1), 17648-17648 (2023-10-18)
Congenital disorders of glycosylation (CDG) are rare genetic disorders with a spectrum of clinical manifestations caused by abnormal N-glycosylation of secreted and cell surface proteins. Over 130 genes are implicated and next generation sequencing further identifies potential disease drivers in
Laïla Giordano et al.
Molecular plant pathology, 23(12), 1783-1791 (2022-09-15)
The phytohormone abscisic acid (ABA) regulates cell growth and plant development, and contributes to defence responses to pathogens. We previously showed that the Arabidopsis malectin-like domain leucine-rich repeat receptor-like kinase (MLD-LRR-RLK) impaired oomycete susceptibility 1 (IOS1) attenuates ABA signalling during
Ping-Yuan Wang et al.
Proceedings of the National Academy of Sciences of the United States of America, 120(34), e2302738120-e2302738120 (2023-08-14)
Myalgic encephalomyelitis/chronic fatigue syndrome (ME/CFS) is characterized by various disabling symptoms including exercise intolerance and is diagnosed in the absence of a specific cause, making its clinical management challenging. A better understanding of the molecular mechanism underlying this apparent bioenergetic

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