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T7765

Tunicamycin

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

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关于此项目

化学文摘社编号:
11089-65-9
UNSPSC Code:
51111800
PubChem Substance ID:
57654701
NACRES:
NA.77
Beilstein/REAXYS Number:
6888090
MDL number:
MFCD00065709
Quality level:
300
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产品名称

衣霉素 来源于链霉菌 属,

Quality Level

300

solubility

95% ethanol: soluble 1 mg/mL, clear to faintly hazy, THF: soluble <1 mg/mL, dioxane: soluble <1 mg/mL, DMF: soluble >10 mg/mL, pyridine: >10 mg/mL, DMSO: soluble 4.9-5.1 mg/mL, clear to slightly hazy, colorless to yellow, methanol: slightly soluble 4.9-5.1 mg/mL, methanol: soluble 4.9-5.1 mg/mL, clear to slightly hazy, colorless to yellow, acetone: insoluble, aqueous base: insoluble, chloroform: insoluble, ethyl acetate: insoluble

antibiotic activity spectrum

fungi, viruses

mode of action

protein synthesis | interferes

storage temp.

2-8°C

SMILES string

CC(C)CCCCCCCC\C=C\C(=O)N[C@@H]1[C@@H](O)[C@@H](O)[C@@H](C[C@@H](O)[C@H]2O[C@H]([C@H](O)[C@@H]2O)N3C=CC(=O)NC3=O)O[C@H]1O[C@@H]4O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]4NC(C)=O

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

InChI key

YJQCOFNZVFGCAF-WPTOCQRYSA-N

General description

包含同系物A、B、C和D。成分可能因批次而异。标识在标签上的实际含量。
化学结构：核苷
衣霉素是一种抗生素和糖基化抑制剂。作用机制包括抑制人UDP-HexNAc:polyprenol-P HexNAc-1-P酶家族中的GlcNAc磷酸转移酶(GPT)。糖基化是一种主要的翻译后修饰，在糖蛋白的折叠、稳定性、亚细胞定位和糖蛋白生物功能中起关键作用。研究发现异常糖基化是癌症特征，在肿瘤演进、转移和化学抗性中占据重要地位。研究表明，衣霉素具有抗肿瘤作用。此外，衣霉素可抑制N-糖基化，以至内质网(ER)腔因积聚未结构化蛋白而发生内质网应激。衣霉素还具有抗细菌和抗真菌作用。它通过抑制N-乙酰氨基葡糖1-磷酸转移至多萜醇单磷酸酯而阻断蛋白质N-糖苷键的形成。衣霉素还抑制细菌和真核生物N-乙酰氨基葡萄糖转移酶，并防止N-乙酰氨基葡萄糖脂质中间体的形成。

Application

衣霉素已被用于在HeLa细胞中研究人质子偶联叶酸转运蛋白（HsPCFT）的N联糖基化作用。衣霉素还被用于在COS-7细胞中研究柯萨奇病毒和腺病毒受体（CAR）糖基化的功能作用。衣霉素可在细胞培养实验中用于抑制N-糖基化。

Biochem/physiol Actions

阻断蛋白质N-糖苷键的形成。

Preparation Note

衣霉素可以4.9-5.1 mg/ml溶于DMSO并产生一种透明至略微有点浑浊、无色至黄色的溶液。此外，衣霉素还可溶于DMF（>10 mg/ml）、吡啶（>10 mg/ml）、水（<5 mg/ml, pH 9.0), dioxane (<1 mg/ml) and THF. However, it is insoluble in other organic solvents such as acetone, chloroform, and ethyl acetate, and in aqueous solutions with pH <6. Aqueous solutions can be prepared from stock solutions by diluting with water at pH 8-10 or with buffers with pH >7，最好是>8。衣霉素即使通过加热也不会溶于pH 8的磷酸盐缓冲液以形成1 mg/ml的浓度，但可通过将pH升高至9并重新滴定至pH 7-8来实现溶解性。

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H300

Hazard Classifications

Acute Tox. 1 Oral

存储类别

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

法规信息

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历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
079M4004V
0000116731
0000116730
037M4047V
069M4012V

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全球贸易项目编号

货号GTIN
T7765-1MG04061838446626
T7765-10MG04061837378614
T7765-50MG04061837378621
T7765-5MG04061838446633