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2-Deoxy-D-glucose

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2-Deoxy-D-glucose Basic information
2-Deoxy-D-glucose Chemical Properties
  • Melting point:146-147 °C(lit.)
  • Boiling point:211.61°C (rough estimate)
  • alpha 45.5 º (c=2, H2O)
  • Density 1.1738 (rough estimate)
  • refractive index 46.5 ° (C=1, H2O)
  • storage temp. 2-8°C
  • solubility H2O: 50 mg/mL, clear, colorless to faintly yellow
  • form crystalline
  • pkapK1:12.52 (25°C)
  • color white
  • Water Solubility Soluble in water.
  • Merck 14,2904
  • BRN 1723331
  • InChIKeyPMMURAAUARKVCB-CEZCPVKQSA-N
  • CAS DataBase Reference154-17-6(CAS DataBase Reference)
  • EPA Substance Registry SystemD-arabino-Hexose, 2-deoxy- (154-17-6)
Safety Information
MSDS
2-Deoxy-D-glucose Usage And Synthesis
  • Chemical Propertieswhite to light yellow crystal powde
  • Uses2-deoxy-D-Glucose is a non-metabolizable glucose analog that inhibits phosphorylation of glucose by hexokinase, the first step of glycolysis. This results in the depletion in cellular ATP, the inhibition of protein glycosylation, and the disruption of ER quality control by inducing the unfolded protein response. 2-deoxy-D-Glucose has been shown to cause cell cycle inhibition and cell death in in vitro models of hypoxia, induce autophagy, increase reactive oxygen species production, activate AMPK, and block tumor cell growth in animal models.[Cayman Chemical]
  • Uses2-Deoxy-D-glucose is act as a culture media part in molecular genetics and as a targeted optical imaging agent for fluorescent in vivo imaging. It finds an application in glucoprivic feeding research to invoke and study the processes of counter-regulatory response (CRR). It is utilized in the development of anti-cancer approaches like oxidative stress, radio and chemosensitization.
  • Safety ProfilePoison by subcutaneous route. Moderately toxic by intraperitoneal route. An experimental teratogen. Other experimental reproductive effects. When heated to decomposition it emits acrid smoke and fumes.
  • Purification MethodsCrystallise 2-deoxy--D-glucose from MeOH/Me2CO, Me2CO or butanone to give a mixture of  and  anomers, m 142-144o, [] 18 +38o (35minutes) to +46o (c 0.5, H2O). Recrystallisation from isoPrOH gives mainly the -anomer m 134-136o , [ ] D +156o to +103o (c 0.9, pyridine). 1H NMR studies showed that at 44o in D2O the solution contained 36% of -pyranose and 64% of -pyranose sugar, but furanose structures were undetectable. [Snowden & Fischer J Am Chem Soc 69 1048 1947, derivatives: Bollinger & Schmidt Helv Chim Acta 34 989 1951; see Angyal & Pickles Aust J Chem 25 1711 1972 for ratio of isomers in solution, Beilstein 1 IV 4282.]
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