Description
D-Glucose-6-phosphate is formed in cells when glucose is phosphorylated by hexokinase (or glucokinase) or by the conversion of glucose-1-phosphate by phosphoglucomutase, which is the first step of glycogen synthesis. It is stored as glycogen when blood glucose levels are high. Disruption of D-glucose-6-phosphate activity leads to glycogen storage disease type I or von Gierke’s disease, a group of inherited metabolic diseases characterized by severe hypoglycemia, growth retardation, and hepatomegaly, due to accumulation of glycogen and fat in the liver. D-Glucose-6-phosphate is also the starting molecule of both glycolysis and the pentose phosphate pathways. Because cancer cells adopt glycolysis as a major source of metabolic energy production, and the pentose phosphate pathway plays a role in helping glycolytic cancer cells to meet their anabolic demands, this compound can be used to study the progression of this process.
Chemical Properties
White crystalline solid
General Description
A glycolytic intermediate that also acts as a competitive and reversible inhibitor of hexokinase. Useful in creating an ATP-regenerating system. Causes the release of mitochondrially bound hexokinase in muscle.
Purification Methods
It can be freed from metal impurities as described for glucose-1-phosphate. The solubility of the Na salt is 5% in H2O at 20o. Its barium salt can be purified by solution in dilute HCl and precipitation by neutralising the solution. The precipitate is washed with small volumes of cold water and dried in air. Alternatively the barium salt is dissolved in H2O, 4volumes of EtOH are added, the precipitate is collected, washed with 90% EtOH, absolute EtOH, 75% EtOH/25% Et2O, 25% EtOH/75% Et2O and finally dry Et2O. The dry Barium salt has [] D +17.9o (c 1, H2O). [Beilstein 1 IV.]
References
[1] De Souza, F.I., Zumiotti, A.V., and Da Silva, C.F. Neuregulins 1-α and 1-β on the regeneration the peripheral nerves[J]. Acta Ortop Bras.
[2] AC A. GLUCOSE-6-PHOSPHATE DEHYDROGENASE DEFICIENCY.[J]. Annales de la Societe belge de medecine tropicale, 1963, 151 1: 675. DOI:
10.1056/nejm199106133242415[3] BEUTLER E. Glucose-6-phosphate dehydrogenase deficiency: a historical perspective.[J]. Blood, 2008, 111 1: 16-24. DOI:
10.1182/blood-2007-04-077412[4] K A GUMAA P M. The pentose phosphate pathway of glucose metabolism. Enzyme profiles and transient and steady-state content of intermediates of alternative pathways of glucose metabolism in Krebs ascites cells.[J]. Biochemical Journal, 1969, 115 5: 1009-1029. DOI:
10.1042/bj1151009[5] KRUSHNA C. PATRA Nissim H. The pentose phosphate pathway and cancer[J]. Trends in Biochemical Sciences, 2014, 39 8: Pages 347-354. DOI:
10.1016/j.tibs.2014.06.005
