D-fructose 6-(dihydrogen phosphate) Chemical Properties

alpha 

D21 +2.5° (c = 3), Meyerhof, Lohmann, Biochem. Z. 185, 117 (1927); D +1.2° (c = 0.9), Lohmann, ibid. 262, 145 (1933)

Boiling point:

697.7±65.0 °C(Predicted)

Density 

1.840±0.06 g/cm3(Predicted)

storage temp. 

2-8°C, sealed storage, away from moisture

form 

Solid

pka

1.83±0.10(Predicted)

color 

White to off-white

EPA Substance Registry System

D-Fructose, 6-(dihydrogen phosphate) (643-13-0)

Safety Information

RIDADR 

1759

HazardClass 

8

PackingGroup 

III

D-fructose 6-(dihydrogen phosphate) Usage And Synthesis

Uses

D-Fructose 6-phosphate is an endogenous metabolite in saliva that affects cell growth and autophagy; it can be hydrolyzed by Fructose-1,6-bisphosphatase (FBPase). D-Fructose-6-phosphate can be converted into D-glucose 6-phosphate (HY-112537) by the action of phosphoglucose isomerase. D-Fructose-6-phosphate is a sugar intermediate in the glycolysis pathway and the pentose phosphate pathway. D-Fructose 6-phosphate can be used to study Lewy body dementia[1][2].

Definition

ChEBI: Keto-D-fructose 6-phosphate is the open chain form of D-fructose 6-phosphate. It is functionally related to a D-fructose. It is a conjugate acid of a D-fructose 6-phosphate(2-).

IC 50

Human Endogenous Metabolite

Purification Methods

Crystallise fructose-6-phosphate as the barium salt from water by adding 4-volumes of EtOH. The barium can be removed by passage through the H+ form of a cation exchange resin, and the free acid is collected by freeze-drying. Alternatively the Ba salt is dissolved in H2O, and one equivalent of Na2SO4 is added in small portions with stirring, filter off BaSO4 and freeze dry to give the Na salt. The 6-phosphate hydrolyses more slowly than the 1-phosphate and considerably slower than pyrophosphoric acid (102 times) and triphosphoric acid (103 times). [Neuberg Biochem Zeitschrift 88 432 1918, pKa: Meyerhof & Lohmann Biochem Zeitschrift 185 113, 131 1927, Neuberg et al. Arch Biochem 3 33, 40 1944, Hydrolysis: Friess J Am Chem Soc 74 5521 1954, Beilstein 1 I 464, 1 IV 4423, H 31 537.]

References

[1] Lee N, et al. Endogenous toxic metabolites and implications in cancer therapy. Oncogene. 2020 Aug;39(35):5709-5720. DOI:10.1038/s41388-020-01395-9
[2] Tsuruoka M, et al. Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. DOI:10.1002/elps.201300019
[3] Hardie DG, et al. AMPK: a nutrient and energy sensor that maintains energy homeostasis. Nat Rev Mol Cell Biol. 2012 Mar 22;13(4):251-62. DOI:10.1038/nrm3311

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