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SML1287

Tunicamycin

Name: Tunicamycin
Brand: SIGMA

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

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关于此项目

经验公式（希尔记法）:

C₃₇H₆₀N₄O₁₆

化学文摘社编号:

11089-65-9

分子量:

816.89

UNSPSC Code:

51111800

NACRES:

NA.77

EC Number:

200-664-3

Form:

DMSO solution

Quality level:

200

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属性

产品名称

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

biological source

Streptomyces sp.

Quality Level

200

form

DMSO solution

concentration

5 mg/mL in DMSO

storage temp.

2-8°C

SMILES string

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

说明

General description

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.

Application

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.

Biochem/physiol Actions

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).

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.

存储类别

10 - Combustible liquids

wgk

WGK 1

flash_point_f

188.6 °F

flash_point_c

87 °C

历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

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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)

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)

SQSTM1/p62-mediated autophagy compensates for loss of proteasome polyubiquitin recruiting capacity.

Alik Demishtein et al.

Autophagy, 13(10), 1697-1708 (2017-08-10)

Protein homeostasis in eukaryotic cells is regulated by 2 highly conserved degradative pathways, the ubiquitin-proteasome system (UPS) and macroautophagy/autophagy. Recent studies revealed a coordinated and complementary crosstalk between these systems that becomes critical under proteostatic stress. Under physiological conditions, however

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全球贸易项目编号

货号	GTIN
SML1287-1ML	04061838092984