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SMB00932

Sigma-Aldrich

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

≥98% (HPLC)

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C6H13O8P · xNa+
CAS-Nummer:
Molekulargewicht:
244.14 (free acid basis)
MDL-Nummer:
UNSPSC-Code:
12352201
NACRES:
NA.25

Qualitätsniveau

Assay

≥98% (HPLC)

Form

powder

Farbe

white

Löslichkeit

water: 50 mg/mL, clear, colorless

Lagertemp.

−20°C

SMILES String

[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);;

InChIKey

NBDKYLFTCAOTAK-UHFFFAOYSA-N

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Allgemeine Beschreibung

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.

Anwendung

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

Leistungsmerkmale und Vorteile

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

Sonstige Hinweise

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.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°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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