Updated BioCyc iOS App now
available in iTunes store
Updated BioCyc iOS App now
available in iTunes store
Updated BioCyc iOS App now
available in iTunes store
Updated BioCyc iOS App now
available in iTunes store
Updated BioCyc iOS App now
available in iTunes store
twitter

Escherichia coli K-12 substr. MG1655 Compound: β-D-glucopyranose

Synonyms: β-D-glucose, β-glucose

Superclasses: all carbohydratesa carbohydratea glycana sugara monosaccharidea hexosea D-hexosea D-aldohexosea D-aldopyranoseD-glucopyranose
all carbohydratesa carbohydratea glycana sugara monosaccharidea hexosea D-hexosea D-aldohexoseD-glucoseD-glucopyranose
all carbohydratesa carbohydratea glycana sugara monosaccharidea hexosean aldohexosea D-aldohexosea D-aldopyranoseD-glucopyranose
all carbohydratesa carbohydratea glycana sugara monosaccharidea hexosean aldohexosea D-aldohexoseD-glucoseD-glucopyranose
all carbohydratesa carbohydratea glycana sugara monosaccharidea hexoseglucoseD-glucoseD-glucopyranose
all carbohydratesa carbohydratea glycana sugara monosaccharidean aldosea D-aldosea D-aldohexosea D-aldopyranoseD-glucopyranose
all carbohydratesa carbohydratea glycana sugara monosaccharidean aldosea D-aldosea D-aldohexoseD-glucoseD-glucopyranose
all carbohydratesa carbohydratea glycana sugara monosaccharidean aldosean aldohexosea D-aldohexosea D-aldopyranoseD-glucopyranose
all carbohydratesa carbohydratea glycana sugara monosaccharidean aldosean aldohexosea D-aldohexoseD-glucoseD-glucopyranose
all carbohydratesa carbohydratea glycana sugara monosaccharidean aldosean aldopyranosea D-aldopyranoseD-glucopyranose
an aldehyde or ketonean aldehydean aldosea D-aldosea D-aldohexosea D-aldopyranoseD-glucopyranose
an aldehyde or ketonean aldehydean aldosea D-aldosea D-aldohexoseD-glucoseD-glucopyranose
an aldehyde or ketonean aldehydean aldosean aldohexosea D-aldohexosea D-aldopyranoseD-glucopyranose
an aldehyde or ketonean aldehydean aldosean aldohexosea D-aldohexoseD-glucoseD-glucopyranose
an aldehyde or ketonean aldehydean aldosean aldopyranosea D-aldopyranoseD-glucopyranose


Chemical Formula: C6H12O6

Molecular Weight: 180.16 Daltons

Monoisotopic Molecular Weight: 180.0633881178 Daltons

β-D-glucopyranose compound structure

Glycan icon:

β-D-glucopyranose compound structure

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

InChI: InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5-,6-/m1/s1

InChIKey: InChIKey=WQZGKKKJIJFFOK-VFUOTHLCSA-N

Unification Links: CAS:50-99-7, ChEBI:15903, ChemSpider:18802415, DrugBank:DB02379, HMDB:HMDB00516, IAF1260:33582, KEGG:C00221, MetaboLights:MTBLC15903, PubChem:64689

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -218.28

Reactions known to consume the compound:

glucose and glucose-1-phosphate degradation :
D-glucopyranose[periplasm] + a ubiquinone[inner membrane] → D-glucono-1,5-lactone[periplasm] + an ubiquinol[inner membrane]
D-glucopyranose + ATP → D-glucopyranose 6-phosphate + ADP + H+

glycogen degradation I , trehalose degradation I (low osmolarity) , trehalose degradation II (trehalase) :
D-glucopyranose + ATP → D-glucopyranose 6-phosphate + ADP + H+

Not in pathways:
an aldehyde + NADP+ + H2O → a carboxylate + NADPH + 2 H+

Reactions known to produce the compound:

trehalose degradation II (trehalase) , trehalose degradation VI (periplasmic) :
α,α-trehalose + H2O → β-D-glucopyranose + α-D-glucopyranose

Not in pathways:
β-D-glucose 6-phosphate + H2O → β-D-glucopyranose + phosphate

glucose and glucose-1-phosphate degradation :
α-D-glucopyranose 1-phosphate + H2O → D-glucopyranose + phosphate

glycogen degradation I :
maltotetraose + D-glucopyranose ← maltotriose + maltose
maltotriose + H2O → maltose + D-glucopyranose

lactose degradation III :
lactose + H2O → D-galactopyranose + D-glucopyranose

melibiose degradation :
melibiose + H2O → D-galactopyranose + D-glucopyranose

trehalose degradation I (low osmolarity) :
α,α-trehalose 6-phosphate + H2O → D-glucopyranose 6-phosphate + D-glucopyranose

Not in pathways:
isoprimeverose + H2O → D-glucopyranose + α-D-xylopyranose
D-cellobiose 6'-phosphate + H2O → D-glucopyranose 6-phosphate + D-glucopyranose
a β-D glucoside[periplasm] + H2O[periplasm] → a non glucosylated D-glucose acceptor[periplasm] + D-glucopyranose[periplasm]
maltoheptaose + H2O → maltohexaose + D-glucopyranose
maltohexaose + H2O → maltopentaose + D-glucopyranose
GDP-α-D-glucose + H2O → GDP + D-glucopyranose + H+
nigerose + H2O → 2 D-glucopyranose
maltopentaose + H2O → maltotetraose + D-glucopyranose
(1,4-α-D-glucosyl)(n) + H2O → (1,4-α-D-glucosyl)(n-1) + D-glucopyranose
D-glucopyranose 6-phosphate[periplasm] + H2O[periplasm]D-glucopyranose[periplasm] + phosphate[periplasm]
aldehydo-D-glucose → D-glucopyranose

Not in pathways:
a sugar phosphate + H2O → a sugar + phosphate

two-component alkanesulfonate monooxygenase :
an alkylsulfonate + FMNH2 + oxygen → an aldehyde + sulfite + FMN + H2O + 2 H+

Not in pathways:
an aliphatic amine[periplasm] + H2O[periplasm] + oxygen[periplasm]an aldehyde[periplasm] + ammonium[periplasm] + hydrogen peroxide[periplasm]
a primary amine[periplasm] + H2O[periplasm] + oxygen[periplasm]an aldehyde[periplasm] + ammonium[periplasm] + hydrogen peroxide[periplasm]

Reactions known to both consume and produce the compound:

trehalose degradation VI (periplasmic) :
α-D-glucopyranose ↔ β-D-glucopyranose

Not in pathways:
β-D-glucopyranose[periplasm]D-glucose[periplasm]

Not in pathways:
a primary alcohol + NAD+an aldehyde + NADH + H+

In Reactions of unknown directionality:

Not in pathways:
maltopentaose + D-glucopyranose = maltotetraose + maltose
maltohexaose + D-glucopyranose = maltopentaose + maltose
maltose + maltohexaose = maltoheptaose + D-glucopyranose

Not in pathways:
a hexose phosphate + H2O = a hexose + phosphate

Not in pathways:
an aldose[periplasm] + an oxidized unknown electron acceptor[periplasm] + H2O[periplasm] = an aldonate[periplasm] + an reduced unknown electron acceptor[periplasm] + H+[periplasm]

Not in pathways:
an aldehyde[periplasm] + FAD[periplasm] + H2O[periplasm] = a carboxylate[periplasm] + FADH2[periplasm]
an alcohol + NADP+ = an aldehyde + NADPH + H+

In Transport reactions:
HPr-Phis15 + β-D-glucopyranose[periplasm] → β-D-glucose 6-phosphate[cytosol] + HPr,
D-glucopyranose[periplasm]D-glucopyranose[cytosol],
D-glucopyranose[periplasm] + H+[periplasm]D-glucopyranose[cytosol] + H+[cytosol],
a monosaccharide[periplasm]a monosaccharide[extracellular space],
a [PTS enzyme I]-Nπ-phospho-L-histidine + a sugar[periplasm] → a [PTS enzyme I]-L-histidine + a sugar phosphate[cytosol]

In Redox half-reactions:
D-glucono-1,5-lactone[membrane] + 2 H+[membrane] + 2 e-[membrane]D-glucopyranose[membrane]

Enzymes inhibited by β-D-glucopyranose, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: glycogen phosphorylase [Chen68, Comment 1]

This compound has been characterized as an alternative substrate of the following enzymes: aldose sugar dehydrogenase, N-acetyl-D-glucosamine kinase, xylose isomerase, maltose O-acetyltransferase, transport of D-galactose

In Growth Media: MOPS medium with 2% glucose, MOPS medium with 0.4% glucose, Davis and Mingioli glucose minimal medium, Davis and Mingioli medium A, AB medium with 0.2% glucose, M63 medium with 2% glucose, M9 medium with 0.4% glucose, M56 medium, E.coli minimal growth on glucose (example)


References

Chen68: Chen GS, Segel IH (1968). "Purification and properties of glycogen phosphorylase from Escherichia coli." Arch Biochem Biophys 1968;127(1);175-86. PMID: 4878695


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 Pathway Tools version 19.5 (software by SRI International) on Tue Feb 9, 2016, biocyc11.