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Escherichia coli K-12 substr. MG1655 Compound: 2-deoxy-D-glucose

Synonyms: 2-deoxyglucose

Summary:
2-deoxy-D-glucose induces the Sgr mediated glucose stress response in E. coli K-12 which shuts down the ManXYZ system for transport [Rice11]. SetA, encoding a sugar efflux protein is co-transcribed with SgrS under stress conditions [Sun11] leading to the hypothesis that that SetA may export non-metabolisable sugar analogues however the experimental evidence for this is uncertain [Liu99e, Sun11].

Chemical Formula: C6H12O5

Molecular Weight: 164.16 Daltons

Monoisotopic Molecular Weight: 164.0684734957 Daltons

2-deoxy-D-glucose compound structure

SMILES: C1(C(O)OC(CO)C(O)C(O)1)

InChI: InChI=1S/C6H12O5/c7-2-4-6(10)3(8)1-5(9)11-4/h3-10H,1-2H2/t3-,4-,5+,6+/m1/s1

InChIKey: InChIKey=PMMURAAUARKVCB-ZXXMMSQZSA-N

Unification Links: CAS:154-17-6 , ChEBI:84755 , ChemSpider:8709 , KEGG:C00586 , NCI:15193 , PubChem:9062

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -178.44

Reactions known to produce the compound:

Not in pathways:
2-deoxy-D-glucose 6-phosphate + H2O → 2-deoxy-D-glucose + phosphate

In Transport reactions:
2-deoxy-D-glucose[periplasmic space] + HPr-Phis15 → 2-deoxy-D-glucose 6-phosphate[cytosol] + HPr

Enzymes inhibited by 2-deoxy-D-glucose, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: galactose-1-epimerase [Hucho71]

This compound has been characterized as an alternative substrate of the following enzymes: glucose dehydrogenase , transport of D-galactose

Credits:
Last-Curated ? 13-Feb-2013 by Mackie A , Macquarie University


References

Hucho71: Hucho F, Wallenfels K (1971). "The enzymatically catalyzed mutarotaton. The mechanism of action of mutarotase (aldose 1-epimerase) from Escherichia coli." Eur J Biochem 1971;23(3);489-96. PMID: 4945113

Liu99e: Liu JY, Miller PF, Willard J, Olson ER (1999). "Functional and biochemical characterization of Escherichia coli sugar efflux transporters." J Biol Chem 274(33);22977-84. PMID: 10438463

Rice11: Rice JB, Vanderpool CK (2011). "The small RNA SgrS controls sugar-phosphate accumulation by regulating multiple PTS genes." Nucleic Acids Res 39(9);3806-19. PMID: 21245045

Sun11: Sun Y, Vanderpool CK (2011). "Regulation and function of Escherichia coli sugar efflux transporter A (SetA) during glucose-phosphate stress." J Bacteriol 193(1);143-53. PMID: 20971900


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
Page generated by SRI International Pathway Tools version 19.0 on Sat Aug 29, 2015, biocyc14.