Record Information
Version2.0
Creation Date2012-05-31 10:27:09 -0600
Update Date2015-09-13 15:15:19 -0600
Secondary Accession Numbers
  • ECMDB00516
Identification
Name:b-D-Glucose
Description:B-D-glucose is a member of the chemical class known as Hexoses. These are monosaccharides in which the sugar unit is a hexose. Glucose (C6H12O6, also known as D-glucose, dextrose, or grape sugar) is a simple sugar (monosaccharide) and an important carbohydrate in biology. Cells use it as the primary source of energy and a metabolic intermediate. Glucose is one of the main products of photosynthesis and fuels for cellular respiration. Glucose exists in several different molecular structures, but all of these structures can be divided into two families of mirror-images (stereoisomers). Only one set of these isomers exists in nature, those derived from the right-handed form of glucose, denoted D-glucose. D-glucose is sometimes referred to as dextrose, although the use of this name is strongly discouraged. The term dextrose is derived from dextrorotatory glucose. This name is therefore confusing when applied to the enantiomer, which rotates light the opposite direction. Starch and cellulose are polymers derived from the dehydration of D-glucose. The other stereoisomer, called L-glucose, is hardly ever found in nature. (WikiPedia)
Structure
Thumb
Synonyms:
  • β-D-glucopyranose
  • β-glucose
  • 6-(Hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol
  • B-D-Glucopyranose
  • b-delta-Glucopyranose
  • B-Dextrose
  • B-Glucose
  • b-δ-Glucopyranose
  • Beta-D-Glucopyranose
  • Beta-D-Glucose
  • Beta-delta-Glucopyranose
  • Beta-Dextrose
  • Beta-Glucose
  • D-glucose
  • D-Glucose-ring
  • Dextrose
  • Glc
  • Glc-ring
  • Glucose
  • Glucoside
  • β-D-Glucopyranose
  • β-D-Glucose
  • β-Dextrose
  • β-Glucose
  • β-δ-Glucopyranose
Chemical Formula:C6H12O6
Weight:Average: 180.1559
Monoisotopic: 180.063388116
InChI Key:WQZGKKKJIJFFOK-VFUOTHLCSA-N
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
CAS number:492-61-5
IUPAC Name:(2R,3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
Traditional IUPAC Name:glucoside
SMILES:OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentHexoses
Alternative Parents
Substituents
  • Hexose monosaccharide
  • Oxane
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
LogP:-2.912PhysProp
Predicted Properties
PropertyValueSource
Water Solubility782.0 mg/mLALOGPS
logP-2.6ALOGPS
logP-2.9ChemAxon
logS0.64ALOGPS
pKa (Strongest Acidic)11.3ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area110.38 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.92 m3·mol-1ChemAxon
Polarizability16.43 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Galactose metabolismPW000821 Pw000821Pw000821 greyscalePw000821 simple
Secondary metabolites: Trehalose Biosynthesis and MetabolismPW000968 Pw000968Pw000968 greyscalePw000968 simple
Starch and sucrose metabolismPW000941 Pw000941Pw000941 greyscalePw000941 simple
colanic acid building blocks biosynthesisPW000951 Pw000951Pw000951 greyscalePw000951 simple
galactose degradation/Leloir PathwayPW000884 Pw000884Pw000884 greyscalePw000884 simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSsplash10-0np0-9700000000-e8d638dc817e46b97d7bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00di-9721000000-6ca4df9ac892160d11c5View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00di-9621000000-fff85ff382393ec04a54View in MoNA
GC-MSGC-MS Spectrum - GC-MS (5 TMS)splash10-004i-6122690000-eaf6f7adf34ccd0c667bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0900000000-ecd0aedc67c9a2eec60fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ea-2900000000-e4daf22c7320ccc41812View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-9200000000-91fc3940732f782a88bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1900000000-e9f3e728d1b340759a09View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-5900000000-c0a478f2b9c5bbc6c4baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-06852e2088bf1c6b38c4View in MoNA
MSMass Spectrum (Electron Ionization)splash10-03kc-9000000000-a60df7b043f8947d6909View in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference:Wenck, Helmut; Kinedt, Claudia; Bader, Hans Joachim. Production of b-D-glucose. Praxis der Naturwissenschaften, Chemie (1986), 35(4), 23.
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID15903
HMDB IDHMDB00516
Pubchem Compound ID64689
Kegg IDC00221
ChemSpider ID58238
Wikipedia IDNot Available
BioCyc IDGLC
EcoCyc IDGLC
Ligand ExpoBGC

Enzymes

General function:
Involved in beta-galactosidase activity
Specific function:
Hydrolysis of terminal non-reducing beta-D- galactose residues in beta-D-galactosides
Gene Name:
lacZ
Uniprot ID:
P00722
Molecular weight:
116482
Reactions
Hydrolysis of terminal non-reducing beta-D-galactose residues in beta-D-galactosides.
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Hydrolysis of terminal, non-reducing alpha-D- galactose residues in alpha-D-galactosides, including galactose oligosaccharides, galactomannans and galactolipids
Gene Name:
melA
Uniprot ID:
P06720
Molecular weight:
50657
Reactions
Hydrolysis of terminal, non-reducing alpha-D-galactose residues in alpha-D-galactosides, including galactose oligosaccharides, galactomannans and galactolipids.
General function:
Involved in protein-N(PI)-phosphohistidine-sugar phosphotransferase activity
Specific function:
Acts as both a kinase and a phosphatase on BglG
Gene Name:
bglF
Uniprot ID:
P08722
Molecular weight:
66482
Reactions
Protein EIIA N(pi)-phospho-L-histidine + protein EIIB = protein EIIA + protein EIIB N(pi)-phospho-L-histidine/cysteine.
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.
General function:
Involved in glucokinase activity
Specific function:
Not highly important in E.coli as glucose is transported into the cell by the PTS system already as glucose 6-phosphate
Gene Name:
glk
Uniprot ID:
P0A6V8
Molecular weight:
34723
Reactions
ATP + D-glucose = ADP + D-glucose 6-phosphate.
General function:
Involved in aldose 1-epimerase activity
Specific function:
Mutarotase converts alpha-aldose to the beta-anomer. It is active on D-glucose, L-arabinose, D-xylose, D-galactose, maltose and lactose
Gene Name:
galM
Uniprot ID:
P0A9C3
Molecular weight:
38190
Reactions
Alpha-D-glucose = beta-D-glucose.
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Can hydrolyze salicin and arbutin
Gene Name:
bglB
Uniprot ID:
P11988
Molecular weight:
53161
Reactions
6-phospho-beta-D-glucosyl-(1,4)-D-glucose + H(2)O = D-glucose + D-glucose 6-phosphate.
General function:
Involved in catalytic activity
Specific function:
Provides the cells with the ability to utilize trehalose at high osmolarity by splitting it into glucose molecules that can subsequently be taken up by the phosphotransferase-mediated uptake system
Gene Name:
treA
Uniprot ID:
P13482
Molecular weight:
63636
Reactions
Alpha,alpha-trehalose + H(2)O = 2 D-glucose.
General function:
Involved in oxidoreductase activity, acting on CH-OH group of donors
Specific function:
GDH is probably involved in energy conservation rather than in sugar metabolism
Gene Name:
gcd
Uniprot ID:
P15877
Molecular weight:
86747
Reactions
D-glucose + ubiquinone = D-glucono-1,5-lactone + ubiquinol.
General function:
Involved in 4-alpha-glucanotransferase activity
Specific function:
Transfers a segment of a (1->4)-alpha-D-glucan to a new position in an acceptor, which may be glucose or a (1->4)-alpha-D-glucan
Gene Name:
malQ
Uniprot ID:
P15977
Molecular weight:
78503
Reactions
Transfers a segment of a (1->4)-alpha-D-glucan to a new position in an acceptor, which may be glucose or a (1->4)-alpha-D-glucan.
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Hydrolyzes a wide variety of P-beta-glucosides including cellobiose-6P, salicin-6P, arbutin-6P, gentiobiose-6P, methyl- beta-glucoside-6P and p-nitrophenyl-beta-D-glucopyranoside-6P. Is also able to hydrolyze phospho-N,N'-diacetylchitobiose
Gene Name:
chbF
Uniprot ID:
P17411
Molecular weight:
50512
Reactions
6-phospho-beta-D-glucosyl-(1,4)-D-glucose + H(2)O = D-glucose + D-glucose 6-phosphate.
General function:
Involved in protein-N(PI)-phosphohistidine-sugar phosphotransferase activity
Specific function:
MalX encodes a phosphotransferase system enzyme II that can recognize glucose and maltose as substrates even though these sugars may not represent the natural substrates of the system
Gene Name:
malX
Uniprot ID:
P19642
Molecular weight:
56627
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Can hydrolyze salicin, cellobiose, and probably arbutin
Gene Name:
ascB
Uniprot ID:
P24240
Molecular weight:
53935
Reactions
6-phospho-beta-D-glucosyl-(1,4)-D-glucose + H(2)O = D-glucose + D-glucose 6-phosphate.
General function:
Involved in catalytic activity
Specific function:
Alpha,alpha-trehalose 6-phosphate + H(2)O = D- glucose + D-glucose 6-phosphate
Gene Name:
treC
Uniprot ID:
P28904
Molecular weight:
63837
Reactions
Alpha,alpha-trehalose 6-phosphate + H(2)O = D-glucose + D-glucose 6-phosphate.
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Hydrolysis of terminal, non-reducing beta-D- glucosyl residues with release of beta-D-glucose
Gene Name:
bglX
Uniprot ID:
P33363
Molecular weight:
83459
Reactions
Hydrolysis of terminal, non-reducing beta-D-glucosyl residues with release of beta-D-glucose.
General function:
Involved in catalytic activity
Specific function:
Hydrolyzes trehalose to glucose. Could be involved, in cells returning to low osmolarity conditions, in the utilization of the accumulated cytoplasmic trehalose, which was synthesized in response to high osmolarity
Gene Name:
treF
Uniprot ID:
P62601
Molecular weight:
63696
Reactions
Alpha,alpha-trehalose + H(2)O = 2 D-glucose.
General function:
Involved in sugar:hydrogen symporter activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in glucose transport
Gene Name:
crr
Uniprot ID:
P69783
Molecular weight:
18251
Reactions
Protein EIIA N(pi)-phospho-L-histidine + protein EIIB = protein EIIA + protein EIIB N(pi)-phospho-L-histidine/cysteine.
General function:
Involved in protein-N(PI)-phosphohistidine-sugar phosphotransferase activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in glucose transport. This enzyme is also a chemoreceptor monitoring the environment for changes in sugar concentration
Gene Name:
ptsG
Uniprot ID:
P69786
Molecular weight:
50676
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
6-phospho-beta-D-glucosyl-(1,4)-D-glucose + H(2)O = D-glucose + D-glucose 6-phosphate
Gene Name:
bglA
Uniprot ID:
Q46829
Molecular weight:
55361
Reactions
6-phospho-beta-D-glucosyl-(1,4)-D-glucose + H(2)O = D-glucose + D-glucose 6-phosphate.
General function:
carbohydrate metabolic process
Specific function:
Not Available
Gene Name:
lacZ
Uniprot ID:
G0ZKW2
Molecular weight:
116482
Reactions
=

Transporters

General function:
Involved in protein-N(PI)-phosphohistidine-sugar phosphotransferase activity
Specific function:
Acts as both a kinase and a phosphatase on BglG
Gene Name:
bglF
Uniprot ID:
P08722
Molecular weight:
66482
Reactions
Protein EIIA N(pi)-phospho-L-histidine + protein EIIB = protein EIIA + protein EIIB N(pi)-phospho-L-histidine/cysteine.
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.
General function:
Involved in protein-N(PI)-phosphohistidine-sugar phosphotransferase activity
Specific function:
MalX encodes a phosphotransferase system enzyme II that can recognize glucose and maltose as substrates even though these sugars may not represent the natural substrates of the system
Gene Name:
malX
Uniprot ID:
P19642
Molecular weight:
56627
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.
General function:
Involved in protein-N(PI)-phosphohistidine-sugar phosphotransferase activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in glucose transport. This enzyme is also a chemoreceptor monitoring the environment for changes in sugar concentration
Gene Name:
ptsG
Uniprot ID:
P69786
Molecular weight:
50676
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.
General function:
Involved in transmembrane transport
Specific function:
Involved in the efflux of sugars. The physiological role may be the detoxification of non-metabolizable sugar analogs
Gene Name:
setC
Uniprot ID:
P31436
Molecular weight:
43493