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Merck

D3179

2-Desoxi-D-glucosa

≥98% (GC), BioXtra

Sinónimos:

2-Desoxi-D-arabinohexosa

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About This Item

Fórmula empírica (notación de Hill):
C6H12O5
Número CAS:
154-17-6
Peso molecular:
164.16
UNSPSC Code:
12352201
NACRES:
NA.25
PubChem Substance ID:
24893732
EC Number:
205-823-0
Beilstein/REAXYS Number:
1723331
MDL number:
MFCD00151328

Nombre del producto

2-Desoxi-D-glucosa, ≥98% (GC), BioXtra

InChI key

VRYALKFFQXWPIH-PBXRRBTRSA-N

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

SMILES string

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

biological source

synthetic (organic)

product line

BioXtra

assay

≥98% (GC)

form

powder

technique(s)

gas chromatography (GC): suitable

impurities

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

ign. residue

<0.1%

color

white

mp

146-147 °C (lit.)

solubility

H2O: 1 M at 20 °C, clear, colorless

anion traces

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

cation traces

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%

storage temp.

2-8°C

Quality Level

200

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Categorías relacionadas

Biochem/physiol Actions

La 2-desoxi-D-glucosa (2-desoxiglucosa) es un análogo de la glucosa que inhibe la glucólisis a través de sus acciones sobre la hexoquinasa, la etapa limitante de la velocidad de la glucólisis. Es fosforilada por la hexoquinasa a 2-DG-P, que no puede ser metabolizada después por la fosfoglucoisomerasa. Esto provoca la acumulación de 2-DG-P en la célula y el agotamiento del ATP celular. In vitro, se ha demostrado que la 2-desoxiglucosa induce autofagia, aumenta la producción de ROS y activa la 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.

Application

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).

Other Notes

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

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number
0000490669
0000490669
0000438958
0000438957
0000438957

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Encuentre la documentación para los productos que ha comprado recientemente en la Biblioteca de documentos.

Visite la Librería de documentos

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
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
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
Rosemarie Ungricht et al.
The Journal of cell biology, 209(5), 687-703 (2015-06-10)
Newly synthesized membrane proteins are constantly sorted from the endoplasmic reticulum (ER) to various membranous compartments. How proteins specifically enrich at the inner nuclear membrane (INM) is not well understood. We have established a visual in vitro assay to measure
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)
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