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Merck
CN

D3179

Sigma-Aldrich

D-2-脱氧葡萄糖

≥98% (GC), BioXtra

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别名:
2-脱氧-D-葡糖
经验公式(希尔记法):
C6H12O5
CAS号:
分子量:
164.16
Beilstein:
1723331
EC 号:
MDL编号:
UNSPSC代码:
12352201
PubChem化学物质编号:
NACRES:
NA.25

生物来源

synthetic (organic)

质量水平

产品线

BioXtra

检测方案

≥98% (GC)

形式

powder

技术

gas chromatography (GC): suitable

杂质

≤0.001% Phosphorus (P)
<0.1% Insoluble matter

灼烧残渣

<0.1%

颜色

white

mp

146-147 °C (lit.)

溶解性

H2O: 1 M at 20 °C, clear, colorless

痕量阴离子

chloride (Cl-): ≤0.05%
sulfate (SO42-): ≤0.05%

痕量阳离子

Al: ≤0.0005%
Ca: ≤0.003%
Cu: ≤0.0005%
Fe: ≤0.0005%
K: ≤0.005%
Mg: ≤0.001%
NH4+: ≤0.05%
Na: ≤0.005%
Pb: ≤0.001%
Zn: ≤0.0005%

储存温度

2-8°C

SMILES字符串

OC[C@@H](O)[C@@H](O)[C@H](O)CC=O

InChI

1S/C6H12O5/c7-2-1-4(9)6(11)5(10)3-8/h2,4-6,8-11H,1,3H2/t4-,5-,6+/m1/s1

InChI key

VRYALKFFQXWPIH-PBXRRBTRSA-N

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应用

2-Deoxy-D-glucose was used in the development of anti-cancer strategies that involve radio- and chemosensitization and oxidative stress. It was used in glucoprivic feeding research to invoke and study the processes of counter-regulatory response (CRR).

生化/生理作用

2-脱氧-D-葡萄糖(2-脱氧葡萄糖)是一种葡萄糖类似物,可通过作用于己糖激酶这一糖酵解限速步骤来抑制糖酵解。 它会被己糖激酶磷酸化为不能被磷酸葡萄糖异构酶进一步代谢的2-DG-P。 这将导致2-DG-P在细胞中的集聚以及细胞ATP的缺失。在体外,2-脱氧葡萄糖已显示出可诱导自噬、提高ROS的产生并激活AMPK。
2-Deoxy-D-Glucose (2-Deoxyglucose) is a glucose analog that inhibits glycolysis via its action on hexokinase, the rate limiting step of glycolysis. It is phosphorylated by hexokinase to 2-DG-P which can not be further metabolized by phosphoglucose isomerase. This leads to the accumulation of 2-DG-P in the cell and the depletion in cellular ATP. In vitro, 2-Deoxyglucose has been shown to induce autophagy, increases ROS production, and activate AMPK.

其他说明

To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Gloves, type N95 (US)

法规信息

监管及禁止进口产品

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Craig Beall et al.
American journal of physiology. Regulatory, integrative and comparative physiology, 302(2), R215-R223 (2011-11-11)
Despite significant technological and pharmacological advancements, insulin replacement therapy fails to adequately replicate β-cell function, and so glucose control in type 1 diabetes mellitus (T1D) is frequently erratic, leading to periods of hypoglycemia. Moreover, the counterregulatory response (CRR) to falling
Madhusudhanan Sukumar et al.
The Journal of clinical investigation, 123(10), 4479-4488 (2013-10-05)
Naive CD8+ T cells rely upon oxidation of fatty acids as a primary source of energy. After antigen encounter, T cells shift to a glycolytic metabolism to sustain effector function. It is unclear, however, whether changes in glucose metabolism ultimately
Alfredo J Ibáñez et al.
Proceedings of the National Academy of Sciences of the United States of America, 110(22), 8790-8794 (2013-05-15)
Single-cell level measurements are necessary to characterize the intrinsic biological variability in a population of cells. In this study, we demonstrate that, with the microarrays for mass spectrometry platform, we are able to observe this variability. We monitor environmentally (2-deoxy-D-glucose)
B S Dwarakanath
Journal of cancer research and therapeutics, 5 Suppl 1, S27-S31 (2009-12-17)
The glucose analog 2-deoxy-D-glucose (2-DG), an inhibitor of glucose transport and glycolytic ATP production, is the most widely investigated metabolic inhibitor for targeting glucose metabolism. Besides depleting energy in cells, 2-DG has also been found to alter N-linked glycosylation leading
Abdullah Farooque et al.
Journal of cancer research and therapeutics, 5 Suppl 1, S32-S35 (2009-12-17)
Normal tissue toxicity is one of the major limiting factors in cancer therapy. Damage to normal tissues and critical organs restricts the use of higher therapeutic doses thereby compromising the efficacy. The glucose analog 2-deoxy-D-glucose (2-DG), an inhibitor of glycolytic

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