2-Deoxy-D-glucose

2-Deoxy-D-glucose (also known as 2-DDG) 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).

Chemistry

2-Deoxy-D-glucose is a white, crystalline solid with a sweet taste. It is synthesized by replacing the hydroxyl group at the second position of glucose with hydrogen, resulting in the formation of 2-deoxy-D-glucose. This modification renders the molecule unable to undergo further glycolysis.

Biological effects

In cells, 2-Deoxy-D-glucose is taken up by the glucose transporters and is phosphorylated by hexokinase to form 2-deoxy-D-glucose-6-phosphate (2-DG6P). However, unlike glucose-6-phosphate, 2-DG6P cannot proceed further in glycolysis. This results in the competitive inhibition of glucose metabolism.

Medical applications

2-Deoxy-D-glucose has been studied for potential use in cancer treatment. Because cancer cells have a much higher rate of glycolysis, they are much more affected by the inhibition of glycolysis by 2-deoxy-D-glucose. However, the clinical use of 2-deoxy-D-glucose is limited by its toxicity to normal cells.

See also

• Glucose
• Glycolysis
• Hexokinase
• Phosphoglucoisomerase