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Chemical Compound Review:

AC1L9ACM [(2R,3S,4R)-3,4,6- trihydroxyoxan-2...

Synonyms: C06369, 2-Deoxy-D-glucose 6-phosphate, 2-Deoxy-6-O-phospho-D-glucopyranose

Vandenberg, J.I. et al., Vandenberg, J.I. et al., Manuel y Keenoy, B. et al., Walum, E., Thompson, J. et al., et al.

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Disease relevance of C06369

We have investigated the relative contributions of these mechanisms to pHi recovery during respiratory acidosis in the Langendorff-perfused ferret heart with and without correction of extracellular pH (pHo). pHi was measured from the chemical shift of the exogenous 31P nuclear magnetic resonance pH indicator 2-deoxy-D-glucose 6-phosphate [1].

High impact information on C06369

This may be attributable not solely to inhibition of D-glucose phosphorylation by 2-deoxy-D-glucose and 2-deoxy-D-glucose 6-phosphate, but also to inhibition by 2-deoxy-D-glucose 6-phosphate of hexose 6-phosphate interconversion in the reaction catalysed by phosphoglucoisomerase, as also observed with the purified enzyme [2].
Product inhibition of particulate HK activity by glucose 6-phosphate was marked, whereas 2-deoxy-D-glucose 6-phosphate did not inhibit the activity [3].
Enzymatic hydrolysis of 2-deoxy-D-glucose 6-phosphate was inhibited by fluoride when Mg2+ was included in the assay, but only slight inhibition occurred in the presence of Mn2+, Fe2+, or Co2+ [4].
Because of continued dephosphorylation and efflux of the non-metabolizable analog, the maintenance of the intracellular 2-deoxy-D-glucose 6-phosphate pool during growth stasis was dependent upon continued glycolysis [5].
2-DG is transported across the blood-brain barrier into brain tissue where it is phosphorylated to 2-deoxy-D-glucose-6-phosphate (2-DG-6-P) but not metabolized further [6].

Anatomical context of C06369

Time course of radiolabeled 2-deoxy-D-glucose 6-phosphate turnover in cerebral cortex of goats [7].
After 1 h of preincubation of Caco-2 cells in substrate-free transport medium, however, steady-state DG uptake matches 2-deoxy-D-glucose 6-phosphate (DG-6-P) accumulation with undetectable levels of free DG [8].

Associations of C06369 with other chemical compounds

In the Langendorff-perfused heart, washout of CO2 brought about by switching perfusion between 25 mM HCO3(-)-5% CO2-buffered solution and nominally HCO3(-)-CO2-free solution caused a transient rise in intracellular pH (pHi) measured by the chemical shift of 2-deoxy-D-glucose 6-phosphate with 31P nuclear magnetic resonance spectroscopy [9].

Gene context of C06369

The inhibition of bovine heart hexokinase by 2-deoxy-D-glucose-6-phosphate: characterization by 31P NMR and metabolic implications [10].

Analytical, diagnostic and therapeutic context of C06369

Upon perfusion the preloaded cultures slowly released radioactivity as [3H] 2-deoxy-D-glucose-6-phosphate ([3H]dGlc-6-P) (rate const. = 0.017 min-1) from a pool corresponding to 74% (t1/2 = 41 min) of the total radioactivity incorporated [11].

References

Intracellular pH recovery during respiratory acidosis in perfused hearts. Vandenberg, J.I., Metcalfe, J.C., Grace, A.A. Am. J. Physiol. (1994) [Pubmed]
Dissociated effects of 2-deoxy-D-glucose on D-[2-3H]glucose and D-[5-3H]glucose conversion into 3HOH in rat erythrocytes. Manuel y Keenoy, B., Zähner, D., Malaisse, W.J. Biochem. J. (1992) [Pubmed]
Retinal hexokinase: kinetic properties and the effect of cyclic 3',5'-adenosine monophosphate. Liu, S.S., Witkovsky, P., Yang, C.Y. J. Neurochem. (1983) [Pubmed]
Intracellular hexose-6-phosphate:phosphohydrolase from Streptococcus lactis: purification, properties, and function. Thompson, J., Chassy, B.M. J. Bacteriol. (1983) [Pubmed]
Novel phosphoenolpyruvate-dependent futile cycle in Streptococcus lactis: 2-deoxy-D-glucose uncouples energy production from growth. Thompson, J., Chassy, B.M. J. Bacteriol. (1982) [Pubmed]
The effects of pharmacologic doses of 2-deoxy-D-glucose on local cerebral blood flow in the awake, unrestrained rat. Breier, A., Crane, A.M., Kennedy, C., Sokoloff, L. Brain Res. (1993) [Pubmed]
Time course of radiolabeled 2-deoxy-D-glucose 6-phosphate turnover in cerebral cortex of goats. Pelligrino, D.A., Miletich, D.J., Albrecht, R.F. Am. J. Physiol. (1987) [Pubmed]
2-Deoxyglucose transport and metabolism in Caco-2 cells. Bissonnette, P., Gagné, H., Blais, A., Berteloot, A. Am. J. Physiol. (1996) [Pubmed]
Carbonic anhydrase and cardiac pH regulation. Vandenberg, J.I., Carter, N.D., Bethell, H.W., Nogradi, A., Ridderstråle, Y., Metcalfe, J.C., Grace, A.A. Am. J. Physiol. (1996) [Pubmed]
The inhibition of bovine heart hexokinase by 2-deoxy-D-glucose-6-phosphate: characterization by 31P NMR and metabolic implications. Chen, W., Guéron, M. Biochimie (1992) [Pubmed]
Membrane lesions in cultured mouse neuroblastoma cells exposed to metal compounds. Walum, E. Toxicology (1982) [Pubmed]

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