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alpha-D-Glucose (ECMDB03345) (M2MDB000492)
Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 13:58:38 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-09-13 12:56:12 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | alpha-D-Glucose | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | Alpha-D-Glucose is a primary source of energy for living organisms. It is naturally occurring and is found in fruits and other parts of plants in its free state. Alpha-D-Glucose is an intermediate in glycolysis/gluconeogenesis pathway where it is converted to beta-D-glucose via galactose-1-epimerase (mutarotase) (EC:5.1.3.3). It is also involved in several other metabolic pathways: fructose and mannose metabolism, galactose metabolism, starch and sucrose metabolism and amino sugar and nucleotide sugar metabolism. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C6H12O6 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 180.1559 Monoisotopic: 180.063388116 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | WQZGKKKJIJFFOK-DVKNGEFBSA-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: | 492-62-6 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | (2S,3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | α-glucose | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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: | 146 °C | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | D-Maltose + Water <>2 alpha-D-Glucose Sucrose + Water <> beta-D-Fructose + alpha-D-Glucose alpha-D-Glucose <> D-Fructose Glucose 1-phosphate + Water <> alpha-D-Glucose + Phosphate alpha-D-Glucose <> b-D-Glucose alpha-Lactose + Water <> alpha-D-Glucose + D-Galactose Adenosine triphosphate + alpha-D-Glucose <> ADP + Glucose 6-phosphate D-Glucoside + Water <> ROH + alpha-D-Glucose Neohancoside D + Water <> beta-D-Fructose + alpha-D-Glucose alpha-D-Glucose > b-D-Glucose Trehalose + Water > b-D-Glucose + alpha-D-Glucose Trehalose + Water <> b-D-Glucose + alpha-D-Glucose α,α-trehalose + Water > alpha-D-Glucose + Beta-D-Glucose + b-D-Glucose alpha-D-Glucose + HPr - phosphorylated > α-D-glucose 6-phosphate + HPr + Mannose 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: | Simmons, Blake A.; Volponi, Joanne V.; Ingersoll, David; Walker, Andrew. Conversion of sucrose to b-D-glucose using three-stage immobilized enzyme process. U.S. (2007), 12pp. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Download (PDF) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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 xylose isomerase activity
- Specific function:
- D-xylose = D-xylulose
- Gene Name:
- xylA
- Uniprot ID:
- P00944
- Molecular weight:
- 49742
Reactions
D-xylose = D-xylulose. |
- General function:
- Involved in beta-galactosidase activity
- Specific function:
- The wild-type enzyme is an ineffective lactase. Two classes of point mutations dramatically improve activity of the enzyme
- Gene Name:
- ebgA
- Uniprot ID:
- P06864
- Molecular weight:
- 117878
Reactions
Hydrolysis of terminal non-reducing beta-D-galactose residues in beta-D-galactosides. |
- 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 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 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 acid phosphatase activity
- Specific function:
- Absolutely required for the growth of E.coli in a high- phosphate medium containing G-1-P as the sole carbon source
- Gene Name:
- agp
- Uniprot ID:
- P19926
- Molecular weight:
- 45683
Reactions
Alpha-D-glucose 1-phosphate + H(2)O = D-glucose + phosphate. |
- General function:
- Involved in catalytic activity
- Specific function:
- May play a role in regulating the intracellular level of maltotriose. Cleaves glucose from the reducing end of maltotriose and longer maltodextrins with a chain length of up to 7 glucose units
- Gene Name:
- malZ
- Uniprot ID:
- P21517
- Molecular weight:
- 69172
Reactions
Hydrolysis of terminal, non-reducing (1->4)-linked alpha-D-glucose residues with release of alpha-D-glucose. |
- General function:
- Involved in catalytic activity
- Specific function:
- Exhibits hydrolysis activity against alpha-glucosyl fluoride, although natural substrates, such as alpha-glucobioses are scarcely hydrolyzed
- Gene Name:
- yihQ
- Uniprot ID:
- P32138
- Molecular weight:
- 77274
Reactions
Hydrolysis of terminal, non-reducing (1->4)-linked alpha-D-glucose residues with release of alpha-D-glucose. |
- 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:
- Not Available
- Specific function:
- Not Available
- Gene Name:
- ebgC
- Uniprot ID:
- P0AC73
- Molecular weight:
- Not Available
- 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:
- 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. Can transport IPTG, lactose and glucose. Has broad substrate specificity, with preferences for glucosides or galactosides with alkyl or aryl substituents
- Gene Name:
- setA
- Uniprot ID:
- P31675
- Molecular weight:
- 42713
- 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