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Sigma-Aldrich

2-Deoxy-D-glucose

≥98% (GC), crystalline

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Synonym(s):
2-Deoxyglucose, 2-Deoxy-D-arabinohexose
Empirical Formula (Hill Notation):
C6H12O5
CAS Number:
154-17-6
Molecular Weight:
164.16
Beilstein:
1723331
EC Number:
205-823-0
MDL number:
MFCD00151328
PubChem Substance ID:
24894205
NACRES:
NA.25

biological source

synthetic

Quality Level

200

Assay

≥98% (GC)

form

crystalline

technique(s)

gas chromatography (GC): suitable
inhibition assay: suitable

color

white to off-white

mp

146-147 °C (lit.)

solubility

H2O: 0.250 g/5mL

application(s)

clinical research
life science and biopharma
metabolomics

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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General description

2-Deoxy-D-glucose, a non-metabolizable glucose analogue, disrupts glycolysis by targeting hexokinase, the rate-limiting step in glycolysis. Phosphorylated to 2-DG-P by hexokinase, it accumulates in the cell, depleting cellular ATP. This approach, effective in starving and killing cancer cells, may also inhibit virus cells reliant on glycolysis for replication. This versatile molecule finds application in cancer, virology, metabolomics and biochemical research.

Application

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

Biochem/physiol Actions

2-Deoxy-D-Glucose (2-Deoxyglucose) is a glucose analog that inhibits glycolysis via its actions 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, increase ROS production, and activate AMPK.

Features and Benefits

  • High-purity compound suitable for a wide variety of research applications

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research
For additional information on our range of Biochemicals, please complete this form.
To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

comparable product

Product No.
Description
Pricing

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

涉药品监管产品

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Matthew E Mead et al.
mSphere, 4(1) (2019-02-23)
Aspergillus fischeri is closely related to Aspergillus fumigatus, the major cause of invasive mold infections. Even though A. fischeri is commonly found in diverse environments, including hospitals, it rarely causes invasive disease. Why A. fischeri causes less human disease than
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)
Isaline Rowe et al.
Nature medicine, 19(4), 488-493 (2013-03-26)
Autosomal dominant polycystic kidney disease (ADPKD) is a common genetic disorder characterized by bilateral renal cyst formation. Recent identification of signaling cascades deregulated in ADPKD has led to the initiation of several clinical trials, but an approved therapy is still
Melissa A Burmeister et al.
American journal of physiology. Endocrinology and metabolism, 304(7), E677-E685 (2013-01-24)
Glucagon-like peptide-1 (GLP-1) suppresses food intake via activation of a central (i.e., brain) GLP-1 receptor (GLP-1R). Central AMP-activated protein kinase (AMPK) is a nutrient-sensitive regulator of food intake that is inhibited by anorectic signals. The anorectic effect elicited by hindbrain
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Articles

Aerobic Glycolysis and the Warburg Effect

We presents an article about the Warburg effect, and how it is the enhanced conversion of glucose to lactate observed in tumor cells, even in the presence of normal levels of oxygen. Otto Heinrich Warburg demonstrated in 1924 that cancer cells show an increased dependence on glycolysis to meet their energy needs, regardless of whether they were well-oxygenated or not.

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