2-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]
Safety Profile
Poison 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 Methods
Crystallise 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.]