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Merck

SMB00932

Sigma-Aldrich

2-Deoxy-D-glucose 6-phosphate sodium salt

≥98% (HPLC)

Sinónimos:

2-Deoxy-D-glucose 6-phosphate sodium salt

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About This Item

Fórmula empírica (notación de Hill):
C6H13O8P · xNa+
Número de CAS:
Peso molecular:
244.14 (free acid basis)
Número MDL:
Código UNSPSC:
12352201
NACRES:
NA.25

Nivel de calidad

Ensayo

≥98% (HPLC)

Formulario

powder

color

white

solubilidad

water: 50 mg/mL, clear, colorless

temp. de almacenamiento

−20°C

cadena SMILES

[Na].OC(COP(O)(O)=O)C(O)C(O)CC=O

InChI

1S/C6H13O8P.Na.H/c7-2-1-4(8)6(10)5(9)3-14-15(11,12)13;;/h2,4-6,8-10H,1,3H2,(H2,11,12,13);;

Clave InChI

NBDKYLFTCAOTAK-UHFFFAOYSA-N

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Descripción general

2-Deoxy-D-glucose 6-phosphate sodium salt serves as a crucial intermediate in glycogen degradation. Its production in mammalian cells occurs through the action of hexokinase on 2-Deoxy-D-glucose (2-DG).
2-Deoxy-d-glucose (2DG) is a glucose molecule which has the 2-hydroxyl group replaced by hydrogen, so that it cannot undergo further glycolysis. As such, it acts to competitively inhibit the production of glucose-6-phosphate from glucose at the phosphoglucoisomerase level (step 2 of glycolysis). In most cells, glucose hexokinase phosphorylates 2-deoxyglucose, trapping the product 2-deoxyglucose-6-phosphate (2DG6P) intracellularly. 2DG & 2DG6P serve as good markers for tissue glucose uptake and hexokinase activity. For example, many cancers have elevated glucose uptake and hexokinase levels. 2DG6P undergoes only the first enzymatic reaction in the pentose phosphate pathway to generate 2-DG-6-phosphogluconolactone, which cannot be further metabolized.

Aplicación

2-Deoxy-D-glucose 6-phosphate sodium salt is a versatile compound that finds application in metabolomics and biochemical research.

Características y beneficios

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

Otras notas

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.

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable


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Determination of hexokinase activity by formation of 2-deoxy-D-glucose-6-phosphate.
G V TITOVA et al.
Biokhimiia (Moscow, Russia), 26, 706-710 (1962-03-01)
Quentin Defenouillère et al.
Science signaling, 12(597) (2019-09-05)
Anti-cancer strategies that target the glycolytic metabolism of tumors have been proposed. The glucose analog 2-deoxyglucose (2DG) is imported into cells and, after phosphorylation, becomes 2DG-6-phosphate, a toxic by-product that inhibits glycolysis. Using yeast as a model, we performed an

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