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Trehalose 6-phosphate (ECMDB01124) (M2MDB000263)
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Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 13:45:44 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-06-03 15:53:45 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | Trehalose 6-phosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | Trehalose-6-phopshate is a phosphorylated form of trehalose. Trehalose is a disaccharide that acts as an osmoprotectant as well as a carbon source in Escherichia coli. At high osmolarity the cells synthesize large amounts of trehalose internally as an osmoprotectant. However, they can also degrade trehalose as the sole source of carbon under both high- and low-osmolarity growth conditions. The modes of trehalose utilization are different under the two conditions. At low osmolarity, trehalose is transported via a trehalose-specific enzyme of the phosphotransferase system, encoded by treB. The trehalose-6-phosphate formed by this enzyme is hydrolyzed to glucose and glucose 6-phosphate by trehalose-6-phosphate hydrolase, encoded by treC. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C12H23O14P | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 422.2764 Monoisotopic: 422.082541956 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | LABSPYBHMPDTEL-LIZSDCNHSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C12H23O14P/c13-1-3-5(14)7(16)9(18)11(24-3)26-12-10(19)8(17)6(15)4(25-12)2-23-27(20,21)22/h3-19H,1-2H2,(H2,20,21,22)/t3-,4-,5-,6-,7+,8+,9-,10-,11-,12-/m1/s1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | 4484-88-2 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | {[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methoxy}phosphonic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | α,α'-trehalose 6-phosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | OC[C@H]1O[C@H](O[C@H]2O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | belongs to the class of organic compounds known as disaccharide phosphates. These are disaccharides carrying one or more phosphate group on a sugar unit. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Super Class | Organic oxygen compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Class | Organooxygen compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Carbohydrates and carbohydrate conjugates | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | Disaccharide 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: | Phosphoenolpyruvic acid + Trehalose > Pyruvic acid + Trehalose 6-phosphate Glucose 6-phosphate + UDP-Glucose > Hydrogen ion + Trehalose 6-phosphate + Uridine 5'-diphosphate Water + Trehalose 6-phosphate > Phosphate + Trehalose Water + Trehalose 6-phosphate > Glucose 6-phosphate + D-Glucose Water + Trehalose 6-phosphate <> D-Glucose + D-Hexose 6-phosphate UDP-Glucose + Glucose 6-phosphate <> Uridine 5'-diphosphate + Trehalose 6-phosphate Trehalose 6-phosphate + Water <> Trehalose + Phosphate Trehalose + Protein N(pi)-phospho-L-histidine <> Trehalose 6-phosphate + Protein histidine Phosphoenolpyruvic acid + Trehalose > Trehalose 6-phosphate + Pyruvic acid Trehalose 6-phosphate + Water > Glucose 6-phosphate + b-D-Glucose UDP-Glucose + α-D-glucose 6-phosphate > Hydrogen ion + Uridine 5'-diphosphate + Trehalose 6-phosphate UDP-Glucose + Glucose 6-phosphate > Uridine 5'-diphosphate + Trehalose 6-phosphate Trehalose 6-phosphate + Water > Trehalose + Inorganic phosphate Trehalose 6-phosphate + Water <> D-Glucose + Glucose 6-phosphate UDP-Glucose + Alpha-D-glucose 6-phosphate > Uridine 5'-diphosphate + Trehalose 6-phosphate + Hydrogen ion + Uridine 5'-diphosphate Trehalose 6-phosphate + Water > Phosphate + α,α-trehalose α,α-trehalose + HPr - phosphorylated > Trehalose 6-phosphate + HPr | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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: | MacDonald, Donald L.; Wong, Roger Y. K. Chemical synthesis of trehalose 6-phosphate. Biochimica et Biophysica Acta, General Subjects (1964), 86(2), 390-2. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Links: |
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Enzymes
- General function:
- Involved in transferase activity, transferring phosphorus-containing groups
- Specific function:
- General (non sugar-specific) component of the phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS). This major carbohydrate active-transport system catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. Enzyme I transfers the phosphoryl group from phosphoenolpyruvate (PEP) to the phosphoryl carrier protein (HPr)
- Gene Name:
- ptsI
- Uniprot ID:
- P08839
- Molecular weight:
- 63561
Reactions
Phosphoenolpyruvate + protein L-histidine = pyruvate + protein N(pi)-phospho-L-histidine. |
- 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 catalytic activity
- Specific function:
- Catalyzes the transfer of glucose from UDP-glucose to glucose-6-phosphate to form alpha,alpha-1,1 trehalose-6-phosphate. Acts with retention of the anomeric configuration of the UDP-sugar donor. Essential for viability of the cells at low temperatures and at elevated osmotic strength
- Gene Name:
- otsA
- Uniprot ID:
- P31677
- Molecular weight:
- 53611
Reactions
UDP-glucose + D-glucose 6-phosphate = UDP + alpha,alpha-trehalose 6-phosphate. |
- General function:
- Involved in catalytic activity
- Specific function:
- Removes the phosphate from trehalose 6-phosphate to produce free trehalose
- Gene Name:
- otsB
- Uniprot ID:
- P31678
- Molecular weight:
- 29175
Reactions
Trehalose 6-phosphate + H(2)O = trehalose + 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 trehalose transport
- Gene Name:
- treB
- Uniprot ID:
- P36672
- Molecular weight:
- 51080
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar 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 sugar:hydrogen symporter activity
- Specific function:
- General (non sugar-specific) component of the phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS). This major carbohydrate active-transport system catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. The phosphoryl group from phosphoenolpyruvate (PEP) is transferred to the phosphoryl carrier protein HPr by enzyme I. Phospho-HPr then transfers it to the permease (enzymes II/III)
- Gene Name:
- ptsH
- Uniprot ID:
- P0AA04
- Molecular weight:
- 9119
Reactions
Protein HPr N(pi)-phospho-L-histidine + protein EIIA = protein HPr + protein EIIA N(tau)-phospho-L-histidine. |
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 trehalose transport
- Gene Name:
- treB
- Uniprot ID:
- P36672
- Molecular weight:
- 51080
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate. |