D3179

2-Desoxy-D-Glucose

≥98% (GC), BioXtra

• Synonym(e): 2-Desoxy-D-arabinohexose
• Empirische Formel (Hill-System): C₆H₁₂O₅
• CAS-Nummer: 154-17-6
• Molekulargewicht: 164.16
• UNSPSC Code: 12352201
• NACRES: NA.25
• PubChem Substance ID: 24893732
• EC Number: 205-823-0
• Beilstein/REAXYS Number: 1723331
• MDL number: MFCD00151328

Eigenschaften

• biological source: synthetic (organic)
• Quality Segment: 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 (SO₄^2-): ≤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

Beschreibung

Application

2-Deoxy-D-glucose was used in the development of anti-cancer strategies that involve radio- and chemosensitization and oxidative stress.[1][2] It was used in glucoprivic feeding research to invoke and study the processes of counter-regulatory response (CRR).[3]

Biochem/physiol Actions

2-Desoxy-D-glucose (2-Desoxyglucose) ist ein Glucoseanalogon. Sie hemmt die Glycolyse durch ihre Wirkung auf die Hexokinase, welche der geschwindigkeitsbestimmende Schritt der Glycolyse ist. Sie wird von der Hexokinase zu 2-DG-P phosphoryliert. 2-DG-P kann jedoch von der Phosphoglucose-Isomerase nicht weiter metabolisiert werden. Dies führt zur Anhäufung von 2-DG-P in der Zelle und zu einem Mangel an zellulärem ATP. In vitro wurde gezeigt, dass 2-Desoxyglucose Autophagie induziert, die Produktion von reaktiven Sauerstoffspezies (ROS) erhöht und die AMPK aktiviert.

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.[2]

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.

Sicherheitshinweise

• Lagerklasse: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)