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D3179

2-Désoxy-D-glucose

≥98% (GC), BioXtra

Synonyme(s) :

2-Désoxy-D-arabinohexose

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A propos de cet article

Formule empirique (notation de Hill) :
C6H12O5
Numéro CAS:
154-17-6
Poids moléculaire :
164.16
UNSPSC Code:
12352201
NACRES:
NA.25
PubChem Substance ID:
24893732
EC Number:
205-823-0
Beilstein/REAXYS Number:
1723331
MDL number:
MFCD00151328
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biological source

synthetic (organic)

Quality Level

200

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%

application(s)

advanced drug delivery

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

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

Le 2-désoxy-D-glucose (2-désoxyglucose) est un analogue du glucose qui inhibe la glycolyse de par son action sur l′hexokinase, l′étape cinétiquement limitante de la glycolyse. Il est phosphorylé par l′hexokinase en 2-DG-P, un composé qui ne peut pas être métabolisé à son tour par la phosphoglucose isomérase. Il s′ensuit une accumulation de 2-DG-P dans la cellule et une diminution de l′ATP cellulaire. Il a été montré in vitro que le 2-désoxyglucose induit l′autophagie, augmente la production de DRO et active l′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.

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Classe de stockage

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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Certificats d'analyse (COA)

Lot/Batch Number
0000533638
0000533639
0000533637
0000479570
0000479570

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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)
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