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Merck

D3179

Sigma-Aldrich

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 de CAS:
Peso molecular:
164.16
Beilstein/REAXYS Number:
1723331
EC Number:
MDL number:
UNSPSC Code:
12352201
PubChem Substance ID:
NACRES:
NA.25

biological source

synthetic (organic)

Quality Level

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

SMILES string

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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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).

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.

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


Certificados de análisis (COA)

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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
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
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
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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