Glucose 1-phosphate (ECMDB01586) (M2MDB000423)
| Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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| Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Creation Date | 2012-05-31 13:54:41 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Update Date | 2015-10-15 16:14:31 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Secondary Accession Numbers |
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| Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Name: | Glucose 1-phosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | Glucose 1-phosphate is the direct product of the reaction in which glycogen phosphorylase cleaves off a molecule of glucose from a greater glycogen structure. Glycogen phosphorylase, the product of the glgP Gene, catalyzes glycogen breakdown by removing glucose units from the nonreducing ends in Escherichia coli. It cannot travel down many metabolic pathways and must be interconverted by the enzyme phosphoglucomutase in order to become glucose 6-phosphate. In glycogenesis, free glucose 1-phosphate can also react with UTP to form UDP-glucose, by using the enzyme UDP-glucose pyrophosphorylase. Periplasmic acid glucose-1-phosphatase (G-1-Pase) encoded by gene Agp is necessary for the growth of Escherichia coli in a minimal medium containing glucose-1-phosphate (G-1-P) as the sole source of carbon. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Structure |  | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synonyms: |
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| Chemical Formula: | C6H13O9P | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Weight: | Average: 260.1358 Monoisotopic: 260.029718526 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI Key: | HXXFSFRBOHSIMQ-VFUOTHLCSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI: | InChI=1S/C6H13O9P/c7-1-2-3(8)4(9)5(10)6(14-2)15-16(11,12)13/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5-,6-/m1/s1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| CAS number: | 59-56-3 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| IUPAC Name: | {[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Traditional IUPAC Name: | α-D-glucose 1-phosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMILES: | OC[C@H]1O[C@H](OP(O)(O)=O)[C@H](O)[C@@H](O)[C@@H]1O | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Super Class | Organic oxygen compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Class | Organooxygen compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Sub Class | Carbohydrates and carbohydrate conjugates | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Direct Parent | Monosaccharide phosphates | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Alternative Parents | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Substituents |
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| Molecular Framework | Aliphatic heteromonocyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Descriptors |
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| Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Charge: | -2 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Melting point: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Experimental Properties: |
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| Predicted Properties |
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| Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Reactions: | Thymidine 5'-triphosphate + Glucose 1-phosphate + Hydrogen ion <> dTDP-D-Glucose + Pyrophosphate Glucose 1-phosphate <> Glucose 6-phosphate branching glycogen + Phosphate > Glucose 1-phosphate Glycogen + Phosphate > Glucose 1-phosphate Water + UDP-Glucose > Glucose 1-phosphate +2 Hydrogen ion + Uridine 5'-monophosphate Galactose 1-phosphate + UDP-Glucose <> Glucose 1-phosphate + Uridine diphosphategalactose Glucose 1-phosphate + Water > D-Glucose + Phosphate Glucose 1-phosphate + Hydrogen ion + Uridine triphosphate <> Pyrophosphate + UDP-Glucose Maltoheptaose + Phosphate <> Glucose 1-phosphate + Maltohexaose Maltohexaose + Phosphate <> Glucose 1-phosphate + Maltopentaose Maltopentaose + Phosphate <> Glucose 1-phosphate + Maltotetraose Adenosine triphosphate + Glucose 1-phosphate + Hydrogen ion <> ADP-Glucose + Pyrophosphate UDP-Glucose + Water <> Uridine 5'-monophosphate + Glucose 1-phosphate Uridine triphosphate + Glucose 1-phosphate <> Pyrophosphate + UDP-Glucose Sucrose + Phosphate <> D-Fructose + Glucose 1-phosphate Glucose 1-phosphate + Water <> alpha-D-Glucose + Phosphate Adenosine triphosphate + Glucose 1-phosphate <> Pyrophosphate + ADP-Glucose Starch + Phosphate <> 1,4-alpha-D-glucan + Glucose 1-phosphate Thymidine 5'-triphosphate + Glucose 1-phosphate <> Pyrophosphate + dTDP-D-Glucose Glucose 1-phosphate <> D-Hexose 6-phosphate + Glucose 6-phosphate Glucose 1-phosphate > beta-D-Glucose 1-phosphate Hydrogen ion + Glucose 1-phosphate + Adenosine triphosphate > ADP-Glucose + Pyrophosphate Hydrogen ion + Glucose 1-phosphate + Uridine triphosphate > UDP-Glucose + Pyrophosphate Water + Glucose 1-phosphate > Phosphate + D-glucose Glycogen + Phosphate <> a limit dextrin + Glucose 1-phosphate Glucose 1-phosphate <> α-D-glucose 6-phosphate More...Maltotetraose + Phosphate <> Maltotriose + Glucose 1-phosphate a 1,4-α-D-glucan + Phosphate <> a 1,4-α-D-glucan + Glucose 1-phosphate Glucose 1-phosphate + Water <> D-Glucose + Phosphate Sucrose + Phosphate <> D-Fructose + Glucose 1-phosphate Phosphate <> Glucose 1-phosphate Glucose 1-phosphate + Uridine triphosphate + Hydrogen ion + Uridine triphosphate > Pyrophosphate + UDP-Glucose Galactose 1-phosphate + Galactose 1-phosphate > Glucose 1-phosphate Galactose 1-phosphate + UDP-Glucose + Galactose 1-phosphate > Uridine diphosphategalactose + Glucose 1-phosphate + Uridine diphosphategalactose Thymidine 5'-triphosphate + Hydrogen ion + Glucose 1-phosphate > Pyrophosphate + dTDP-D-Glucose Glucose 1-phosphate + Thymidine 5'-triphosphate + Hydrogen ion > Pyrophosphate + TDP-Glucose Glucose 1-phosphate + Hydrogen ion + Uridine triphosphate <> Pyrophosphate + UDP-Glucose Uridine triphosphate + Glucose 1-phosphate <> Pyrophosphate + UDP-Glucose Starch + Phosphate <> 1,4-alpha-D-glucan + Glucose 1-phosphate Phosphate <> Glucose 1-phosphate Glucose 1-phosphate <> Glucose 6-phosphate Thymidine 5'-triphosphate + Glucose 1-phosphate + Hydrogen ion <> dTDP-D-Glucose + Pyrophosphate Starch + Phosphate <> 1,4-alpha-D-glucan + Glucose 1-phosphate Glucose 1-phosphate <> Glucose 6-phosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMPDB Pathways: |
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| KEGG Pathways: |
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| EcoCyc Pathways: |
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| Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Find out more about how we convert literature concentrations. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References: |
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| Synthesis Reference: | Weinhausel, Andreas; Nidetzky, Bernd; Kysela, Christian; Kulbe, Klaus D. Application of Escherichia coli maltodextrin-phosphorylase for the continuous production of glucose-1-phosphate. Enzyme and Microbial Technology (1995), 17(2), 140-6. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Material Safety Data Sheet (MSDS) | Download (PDF) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Enzymes
- General function:
- Involved in phosphorylase activity
- Specific function:
- Phosphorylase is an important allosteric enzyme in carbohydrate metabolism. Enzymes from different sources differ in their regulatory mechanisms and in their natural substrates. However, all known phosphorylases share catalytic and structural properties
- Gene Name:
- malP
- Uniprot ID:
- P00490
- Molecular weight:
- 90522
Reactions
| (1,4-alpha-D-glucosyl)(n) + phosphate = (1,4-alpha-D-glucosyl)(n-1) + alpha-D-glucose 1-phosphate. |
- General function:
- Involved in hydrolase activity
- Specific function:
- Degradation of external UDP-glucose to uridine monophosphate and glucose-1-phosphate, which can then be used by the cell
- Gene Name:
- ushA
- Uniprot ID:
- P07024
- Molecular weight:
- 60824
Reactions
| UDP-sugar + H(2)O = UMP + alpha-D-aldose 1-phosphate. |
| A 5'-ribonucleotide + H(2)O = a ribonucleoside + phosphate. |
- General function:
- Involved in UDP-glucose:hexose-1-phosphate uridylyltransferase activity
- Specific function:
- UDP-glucose + alpha-D-galactose 1-phosphate = alpha-D-glucose 1-phosphate + UDP-galactose
- Gene Name:
- galT
- Uniprot ID:
- P09148
- Molecular weight:
- 39645
Reactions
| UDP-glucose + alpha-D-galactose 1-phosphate = alpha-D-glucose 1-phosphate + UDP-galactose. |
- General function:
- Involved in glycogen biosynthetic process
- Specific function:
- ATP + alpha-D-glucose 1-phosphate = diphosphate + ADP-glucose
- Gene Name:
- glgC
- Uniprot ID:
- P0A6V1
- Molecular weight:
- 48697
Reactions
| ATP + alpha-D-glucose 1-phosphate = diphosphate + ADP-glucose. |
- General function:
- Involved in enzyme regulator activity
- Specific function:
- UTP + alpha-D-glucose 1-phosphate = diphosphate + UDP-glucose
- Gene Name:
- galF
- Uniprot ID:
- P0AAB6
- Molecular weight:
- 32829
Reactions
| UTP + alpha-D-glucose 1-phosphate = diphosphate + UDP-glucose. |
- General function:
- Involved in phosphorylase activity
- Specific function:
- Phosphorylase is an important allosteric enzyme in carbohydrate metabolism. Enzymes from different sources differ in their regulatory mechanisms and in their natural substrates. However, all known phosphorylases share catalytic and structural properties
- Gene Name:
- glgP
- Uniprot ID:
- P0AC86
- Molecular weight:
- 93172
Reactions
| (1,4-alpha-D-glucosyl)(n) + phosphate = (1,4-alpha-D-glucosyl)(n-1) + alpha-D-glucose 1-phosphate. |
- General function:
- Involved in UTP:glucose-1-phosphate uridylyltransferase activity
- Specific function:
- May play a role in stationary phase survival
- Gene Name:
- galU
- Uniprot ID:
- P0AEP3
- Molecular weight:
- 32942
Reactions
| UTP + alpha-D-glucose 1-phosphate = diphosphate + UDP-glucose. |
- General function:
- Involved in nucleoside-triphosphate diphosphatase activity
- Specific function:
- Specific function unknown
- Gene Name:
- mazG
- Uniprot ID:
- P0AEY3
- Molecular weight:
- 30412
Reactions
| ATP + H(2)O = AMP + diphosphate. |
- 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 intramolecular transferase activity, phosphotransferases
- Specific function:
- This enzyme participates in both the breakdown and synthesis of glucose
- Gene Name:
- pgm
- Uniprot ID:
- P36938
- Molecular weight:
- 58361
Reactions
| Alpha-D-glucose 1-phosphate = alpha-D-glucose 6-phosphate. |
- General function:
- Involved in glucose-1-phosphate thymidylyltransferase activity
- Specific function:
- Catalyzes the formation of dTDP-glucose, from dTTP and glucose 1-phosphate, as well as its pyrophosphorolysis
- Gene Name:
- rmlA1
- Uniprot ID:
- P37744
- Molecular weight:
- 32693
Reactions
| dTTP + alpha-D-glucose 1-phosphate = diphosphate + dTDP-glucose. |
- General function:
- Involved in glucose-1-phosphate thymidylyltransferase activity
- Specific function:
- Catalyzes the formation of dTDP-glucose, from dTTP and glucose 1-phosphate, as well as its pyrophosphorolysis
- Gene Name:
- rmlA2
- Uniprot ID:
- P61887
- Molecular weight:
- 32734
Reactions
| dTTP + alpha-D-glucose 1-phosphate = diphosphate + dTDP-glucose. |
- General function:
- Involved in catalytic activity
- Specific function:
- Sucrose + phosphate = D-fructose + alpha-D- glucose 1-phosphate
- Gene Name:
- ycjM
- Uniprot ID:
- P76041
- Molecular weight:
- 64185
Reactions
| Sucrose + phosphate = D-fructose + alpha-D-glucose 1-phosphate. |
- General function:
- Involved in catalytic activity
- Specific function:
- Catalyzes the dephosphorylation of the artificial chromogenic substrate p-nitrophenyl phosphate (pNPP) and of the natural substrates fructose 1-phosphate and 6-phosphogluconate
- Gene Name:
- yqaB
- Uniprot ID:
- P77475
- Molecular weight:
- 20780
Transporters
- General function:
- Involved in transporter activity
- Specific function:
- Non-specific porin
- Gene Name:
- ompN
- Uniprot ID:
- P77747
- Molecular weight:
- 41220
- General function:
- Involved in transporter activity
- Specific function:
- Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
- Gene Name:
- phoE
- Uniprot ID:
- P02932
- Molecular weight:
- 38922
- General function:
- Involved in transporter activity
- Specific function:
- OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
- Gene Name:
- ompF
- Uniprot ID:
- P02931
- Molecular weight:
- 39333
- General function:
- Involved in transporter activity
- Specific function:
- Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
- Gene Name:
- ompC
- Uniprot ID:
- P06996
- Molecular weight:
- 40368