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

Synonyms: β-D-glucose, β-glucose

Superclasses: all carbohydrates a carbohydrate a glycan a sugar a monosaccharide a hexose a D-hexose a D-aldohexose a D-aldopyranose D-glucopyranose
all carbohydrates a carbohydrate a glycan a sugar a monosaccharide a hexose a D-hexose a D-aldohexose D-glucose D-glucopyranose
all carbohydrates a carbohydrate a glycan a sugar a monosaccharide a hexose an aldohexose a D-aldohexose a D-aldopyranose D-glucopyranose
all carbohydrates a carbohydrate a glycan a sugar a monosaccharide a hexose an aldohexose a D-aldohexose D-glucose D-glucopyranose
all carbohydrates a carbohydrate a glycan a sugar a monosaccharide a hexose glucose D-glucose D-glucopyranose
all carbohydrates a carbohydrate a glycan a sugar a monosaccharide an aldose a D-aldose a D-aldohexose a D-aldopyranose D-glucopyranose
all carbohydrates a carbohydrate a glycan a sugar a monosaccharide an aldose a D-aldose a D-aldohexose D-glucose D-glucopyranose
all carbohydrates a carbohydrate a glycan a sugar a monosaccharide an aldose an aldohexose a D-aldohexose a D-aldopyranose D-glucopyranose
all carbohydrates a carbohydrate a glycan a sugar a monosaccharide an aldose an aldohexose a D-aldohexose D-glucose D-glucopyranose
all carbohydrates a carbohydrate a glycan a sugar a monosaccharide an aldose an aldopyranose a D-aldopyranose D-glucopyranose
an aldehyde or ketone an aldehyde an aldose a D-aldose a D-aldohexose a D-aldopyranose D-glucopyranose
an aldehyde or ketone an aldehyde an aldose a D-aldose a D-aldohexose D-glucose D-glucopyranose
an aldehyde or ketone an aldehyde an aldose an aldohexose a D-aldohexose a D-aldopyranose D-glucopyranose
an aldehyde or ketone an aldehyde an aldose an aldohexose a D-aldohexose D-glucose D-glucopyranose
an aldehyde or ketone an aldehyde an aldose an aldopyranose a D-aldopyranose D-glucopyranose

Chemical Formula: C6H12O6

Molecular Weight: 180.16 Daltons

Monoisotopic Molecular Weight: 180.0633881178 Daltons

β-D-glucopyranose compound structure

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 , trehalose degradation II (trehalase) :
β-D-glucopyranose + ATP → β-D-glucose 6-phosphate + ADP + H+

Not in pathways:
β-D-glucopyranose[periplasmic space] + a ubiquinone[inner membrane] → D-glucono-1,5-lactone[periplasmic space] + an ubiquinol[inner membrane]

glucose and glucose-1-phosphate degradation :
D-glucopyranose[periplasmic space] + a ubiquinone[inner membrane] → D-glucono-1,5-lactone[periplasmic space] + an ubiquinol[inner membrane]

glycogen degradation I (bacterial) , trehalose degradation I (low osmolarity) :
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:

lactose degradation III :
α-lactose + H2O → β-D-galactose + β-D-glucopyranose

melibiose degradation :
melibiose + H2O → α-D-galactose + β-D-glucopyranose

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

Not in pathways:
β-D-cellobiose 6'-phosphate + H2O → β-D-glucose 6-phosphate + β-D-glucopyranose
GDP-α-D-glucose + H2O → β-D-glucopyranose + GDP + H+
a β-D glucoside[periplasmic space] + H2O[periplasmic space] → a non glucosylated D-glucose acceptor[periplasmic space] + β-D-glucopyranose[periplasmic space]
isoprimeverose + H2O → β-D-glucopyranose + α-D-xylopyranose
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 (bacterial) :
maltotetraose + D-glucopyranose ← maltotriose + maltose
maltotriose + H2O → maltose + D-glucopyranose

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

Not in pathways:
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[periplasmic space] + H2O[periplasmic space]D-glucopyranose[periplasmic space] + phosphate[periplasmic space]
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[periplasmic space] + H2O[periplasmic space] + oxygen[periplasmic space]an aldehyde[periplasmic space] + ammonium[periplasmic space] + hydrogen peroxide[periplasmic space]
a primary amine[periplasmic space] + H2O[periplasmic space] + oxygen[periplasmic space]an aldehyde[periplasmic space] + ammonium[periplasmic space] + hydrogen peroxide[periplasmic space]

Reactions known to both consume and produce the compound:

trehalose degradation II (trehalase) , trehalose degradation VI (periplasmic) :
α-D-glucose ↔ β-D-glucopyranose

Not in pathways:
β-D-glucopyranose[periplasmic space]D-glucose[periplasmic space]

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

In Reactions of unknown directionality:

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

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

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

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

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

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

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

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: N-acetyl-D-glucosamine kinase , maltose acetyltransferase , transport of D-galactose , aldose sugar dehydrogenase , xylose isomerase

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


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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, BIOCYC14B.