L-Ascorbate 6-phosphate (ECMDB20164) (M2MDB001011)
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Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 14:30:53 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-09-17 15:41:58 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | L-Ascorbate 6-phosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | L-ascorbate 6-phosphate is a member of the chemical class known as Organophosphate Esters. These are organic compounds containing phosphoric acid ester functional group. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C6H6O9P | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 253.08 Monoisotopic: 252.976589511 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | KIENGQUGHPTFGC-JLAZNSOCSA-K | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C6H9O9P/c7-2(1-14-16(11,12)13)5-3(8)4(9)6(10)15-5/h2,5,7-9H,1H2,(H2,11,12,13)/p-3/t2-,5+/m0/s1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | [(2S)-2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethoxy]phosphonic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | L-ascorbyl phosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | [H][C@@]1(OC(=O)C(O)=C1[O-])[C@@H](O)COP([O-])([O-])=O | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Super Class | Organic acids and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Class | Organic phosphoric acids and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Phosphate esters | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | Monoalkyl phosphates | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Alternative Parents | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Substituents |
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Molecular Framework | Aliphatic heteromonocyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors |
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Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | -3 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | Phosphoenolpyruvic acid + Ascorbic acid > L-Ascorbate 6-phosphate + Pyruvic acid L-Ascorbate 6-phosphate + Water > 3-Dehydro-L-gulonate 6-phosphate + Hydrogen ion Protein N(pi)-phospho-L-histidine + Ascorbic acid <> Protein histidine + L-Ascorbate 6-phosphate L-Ascorbate 6-phosphate + Water <> 3-Dehydro-L-gulonate 6-phosphate Phosphoenolpyruvic acid + Ascorbic acid > L-Ascorbate 6-phosphate + Pyruvic acid L-Ascorbate 6-phosphate + Water > 3-Dehydro-L-gulonate 6-phosphate L-ascorbate 6-phosphate + Water + L-Ascorbate 6-phosphate > 3-keto-L-gulonate 6-phosphate + 3-Keto-L-gulonate 6-phosphate Ascorbic acid + HPr - phosphorylated + Ascorbic acid > L-ascorbate 6-phosphate + HPr + L-Ascorbate 6-phosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMPDB Pathways: |
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KEGG Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
EcoCyc Pathways: |
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Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: |
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References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
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Synthesis Reference: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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 phosphoenolpyruvate-dependent sugar phosphotransferase system
- 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
- Gene Name:
- yadI
- Uniprot ID:
- P36881
- Molecular weight:
- 16540
Reactions
Protein EIIA N(pi)-phospho-L-histidine + protein EIIB = protein EIIA + protein EIIB N(pi)-phospho-L-histidine/cysteine. |
- General function:
- Involved in transporter 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 ascorbate transport
- Gene Name:
- ulaC
- Uniprot ID:
- P69820
- Molecular weight:
- 17237
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:
- 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 ascorbate transport
- Gene Name:
- ulaB
- Uniprot ID:
- P69822
- Molecular weight:
- 10896
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate. |
- General function:
- Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
- Specific function:
- The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active- transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in ascorbate transport
- Gene Name:
- ulaA
- Uniprot ID:
- P39301
- Molecular weight:
- 50737
- General function:
- Involved in hydrolase activity
- Specific function:
- Probably catalyzes the hydrolysis of L-ascorbate-6-P into 3-keto-L-gulonate-6-P. Is essential for L-ascorbate utilization under anaerobic conditions. Also shows phosphodiesterase activity, hydrolyzing phosphodiester bond in the artificial chromogenic substrate bis-p-nitrophenyl phosphate (bis- pNPP)
- Gene Name:
- ulaG
- Uniprot ID:
- P39300
- Molecular weight:
- 40060
Reactions
L-ascorbate 6-phosphate + H(2)O = 3-dehydro-L-gulonate 6-phosphate. |
- 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 phosphoenolpyruvate-dependent sugar phosphotransferase system
- Specific function:
- The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active- transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in ascorbate transport
- Gene Name:
- ulaA
- Uniprot ID:
- P39301
- Molecular weight:
- 50737