b-D-Glucose (ECMDB00516) (M2MDB000145)
Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 10:27:09 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-09-13 15:15:19 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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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 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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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 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | 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. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Super Class | Organic oxygen compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Class | Organooxygen compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Carbohydrates and carbohydrate conjugates | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | Hexoses | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Alternative Parents | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Substituents |
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Molecular Framework | Aliphatic heteromonocyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors |
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Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | Cellobiose + Water <>2 b-D-Glucose Adenosine triphosphate + b-D-Glucose <> ADP + beta-D-Glucose 6-phosphate alpha-D-Glucose <> b-D-Glucose Cellulose + Water <> Cellulose + b-D-Glucose 3-Ketolactose + Water <> 3-Keto-beta-D-galactose + b-D-Glucose b-D-Glucose <> D-glucose Phosphoenolpyruvic acid + b-D-Glucose > Glucose 6-phosphate + Pyruvic acid a β-D glucoside + Water a non glucosylated glucose acceptor + b-D-Glucose Cellobiose-6-phosphate + Water > Glucose 6-phosphate + b-D-Glucose D-Glucose <> b-D-Glucose Water + Melibiose > D-Galactose + b-D-Glucose Maltotriose + D-Maltose <> Maltotetraose + b-D-Glucose Water + alpha-Lactose > D-Galactose + b-D-Glucose GDP-α-D-glucose + Water > Hydrogen ion + b-D-Glucose + Guanosine diphosphate b-D-Glucose + a ubiquinone > Gluconolactone + a ubiquinol b-D-Glucose + Adenosine triphosphate > Hydrogen ion + Glucose 6-phosphate + ADP isoprimeverose + Water b-D-Glucose + D-Xylose Gluconolactone + Hydrogen ion <> b-D-Glucose Trehalose 6-phosphate + Water > Glucose 6-phosphate + b-D-Glucose Trehalose + Water > b-D-Glucose + D-Glucose alpha-D-Glucose > b-D-Glucose Trehalose + Water > b-D-Glucose + alpha-D-Glucose Trehalose + Water <> b-D-Glucose + alpha-D-Glucose alpha-Lactose + Water > beta-D-Galactose + Beta-D-Glucose + b-D-Glucose Beta-D-Glucose + Adenosine triphosphate + b-D-Glucose > Hydrogen ion + Adenosine diphosphate + beta-D-Glucose 6-phosphate + ADP Melibiose + Water > Alpha-D-Galactose + Beta-D-Glucose + b-D-Glucose More...α,α-trehalose + Water > alpha-D-Glucose + Beta-D-Glucose + b-D-Glucose Beta-D-Glucose + HPr - phosphorylated + b-D-Glucose > beta-D-Glucose 6-phosphate + HPr Cellobiose + Water <>2 b-D-Glucose Adenosine triphosphate + b-D-Glucose <> ADP + beta-D-Glucose 6-phosphate Adenosine triphosphate + b-D-Glucose <> ADP + beta-D-Glucose 6-phosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMPDB Pathways: |
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KEGG Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
EcoCyc Pathways: |
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Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
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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 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Links: |
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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