SMB00932
2-Deoxy-D-glucose 6-phosphate sodium salt
≥98% (HPLC)
Synonym(s):
2-Deoxy-D-glucose 6-phosphate sodium salt
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About This Item
Empirical Formula (Hill Notation):
C6H13O8P · xNa+
CAS Number:
Molecular Weight:
244.14 (free acid basis)
MDL number:
UNSPSC Code:
12352201
NACRES:
NA.25
Quality Level
Assay
≥98% (HPLC)
form
powder
color
white
solubility
water: 50 mg/mL, clear, colorless
storage temp.
−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);;
InChI key
NBDKYLFTCAOTAK-UHFFFAOYSA-N
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General description
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.
Application
2-Deoxy-D-glucose 6-phosphate sodium salt is a versatile compound that finds application in metabolomics and biochemical research.
Features and Benefits
- High-purity compound suitable for a wide variety of research applications
Other Notes
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Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Regulatory Information
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危险化学品
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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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