beta-D-Glucose 6-phosphate (ECMDB03498) (M2MDB000506)
Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 13:59:22 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-06-03 15:54:24 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | beta-D-Glucose 6-phosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | Beta-D-Glucose 6 phosphate (b-G6P) is the beta-anomer of glucose-6-phosphate. There are two anomers of glucose 6 phosphate, the alpha anomer and the beta anomer. Specifically, beta-D-Glucose 6-phosphate is glucose sugar phosphorylated on carbon 6. It is a very common metabolite in cells as the vast majority of glucose entering a cell will become phosphorylated in this way. The primary reason for the immediate phosphorylation of glucose is to prevent diffusion out of the cell. The phosphorylation adds a charged phosphate group so the glucose 6-phosphate cannot easily cross the cell membrane. b-G6P is involved in the glycolysis, gluconeogenesis, pentose phosphate, and glycogen and sucrose metabolic pathways [Kegg ID: C01172]. Beta-D-Glucose 6 phosphate can be generated through beta-D-fructose phosphate or alpha-D-glucose 6 phosphate (via glucose-6-phosphate isomerase) or beta-D glucose (via hexokinase). It can then be sent off to the pentose phosphate pathway which generates the useful cofactor NADPH as well as ribulose 5-phosphate, a carbon source for the synthesis of other molecules. Alternately if the cell needs energy or carbon skeletons for synthesis then glucose 6-phosphate is targeted for glycolysis. A third route is to have glucose 6 phosphate stored or converted to glycogen. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Chemical Formula: | C6H13O9P | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 260.1358 Monoisotopic: 260.029718526 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | NBSCHQHZLSJFNQ-VFUOTHLCSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C6H13O9P/c7-3-2(1-14-16(11,12)13)15-6(10)5(9)4(3)8/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5-,6-/m1/s1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | {[(2R,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy}phosphonic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | β-D-glucose 6-phosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | O[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]1O | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Super Class | Organic oxygen compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Class | Organooxygen compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Carbohydrates and carbohydrate conjugates | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | Hexose phosphates | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Alternative Parents | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Substituents |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Molecular Framework | Aliphatic heteromonocyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | -2 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Predicted Properties |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | Adenosine triphosphate + b-D-Glucose <> ADP + beta-D-Glucose 6-phosphate beta-D-Glucose 1-phosphate <> beta-D-Glucose 6-phosphate beta-D-Glucose 6-phosphate + NADP <> 6-Phosphonoglucono-D-lactone + NADPH + Hydrogen ion Glucose 6-phosphate + Alpha-D-glucose 6-phosphate <> beta-D-Glucose 6-phosphate beta-D-Glucose 6-phosphate <> beta-D-Fructose 6-phosphate Arbutin 6-phosphate + Water <> Hydroquinone + beta-D-Glucose 6-phosphate Salicin 6-phosphate + Water <> Salicyl alcohol + beta-D-Glucose 6-phosphate beta-D-Glucose 1-phosphate > beta-D-Glucose 6-phosphate Alpha-D-glucose 6-phosphate > beta-D-Glucose 6-phosphate beta-D-Glucose 6-phosphate + NADP > 6-Phosphonoglucono-D-lactone + NADPH + Hydrogen ion + NADPH beta-D-Glucose 6-phosphate > Fructose 6-phosphate + Fructose 6-phosphate D-tagatofuranose 6-phosphate > beta-D-Glucose 6-phosphate beta-D-Glucose 6-phosphate > beta-D-Fructose 6-phosphate Beta-D-Glucose + Adenosine triphosphate + b-D-Glucose > Hydrogen ion + Adenosine diphosphate + beta-D-Glucose 6-phosphate + ADP D-Glucose + Adenosine triphosphate > Hydrogen ion + Adenosine diphosphate + beta-D-Glucose 6-phosphate + ADP beta-D-Glucose 6-phosphate > β-D-glucose 1-phosphate Beta-D-Glucose + HPr - phosphorylated + b-D-Glucose > beta-D-Glucose 6-phosphate + HPr beta-D-Glucose 6-phosphate + NADP <>6 6-Phosphonoglucono-D-lactone + NADPH + Hydrogen ion Adenosine triphosphate + b-D-Glucose <> ADP + beta-D-Glucose 6-phosphate Glucose 6-phosphate + Alpha-D-glucose 6-phosphate <> beta-D-Glucose 6-phosphate Adenosine triphosphate + b-D-Glucose <> ADP + beta-D-Glucose 6-phosphate Glucose 6-phosphate + Alpha-D-glucose 6-phosphate <> beta-D-Glucose 6-phosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMPDB Pathways: |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
KEGG Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
EcoCyc Pathways: |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synthesis Reference: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Links: |
|
Enzymes
- General function:
- Involved in glucose-6-phosphate isomerase activity
- Specific function:
- D-glucose 6-phosphate = D-fructose 6- phosphate
- Gene Name:
- pgi
- Uniprot ID:
- P0A6T1
- Molecular weight:
- 61529
Reactions
D-glucose 6-phosphate = D-fructose 6-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 glucose-6-phosphate dehydrogenase activity
- Specific function:
- D-glucose 6-phosphate + NADP(+) = D-glucono- 1,5-lactone 6-phosphate + NADPH
- Gene Name:
- zwf
- Uniprot ID:
- P0AC53
- Molecular weight:
- 55704
Reactions
D-glucose 6-phosphate + NADP(+) = 6-phospho-D-glucono-1,5-lactone + NADPH. |
- 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 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 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 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 beta-phosphoglucomutase activity
- Specific function:
- Reversible transformation of glucose 6-phosphate and beta-glucose 1-phosphate
- Gene Name:
- ycjU
- Uniprot ID:
- P77366
- Molecular weight:
- 23565
Reactions
Beta-D-glucose 1-phosphate = beta-D-glucose 6-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:
- Not Available
- Specific function:
- Not Available
- Gene Name:
- yeaD
- Uniprot ID:
- P39173
- Molecular weight:
- Not Available
Transporters
- 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. |