Mannose 6-phosphate (ECMDB01078) (M2MDB000244)
| Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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| Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Creation Date | 2012-05-31 13:44:41 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Update Date | 2015-10-15 16:13:50 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Secondary Accession Numbers |
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| Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Name: | Mannose 6-phosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | Mannose-6-phosphate (M6P) is a molecule bound by lectin. M6P is converted to fructose 6-phosphate by mannose phosphate isomerase. (Wikipedia) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Structure |  | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synonyms: |
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| Chemical Formula: | C6H13O9P | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Weight: | Average: 260.1358 Monoisotopic: 260.029718526 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI Key: | NBSCHQHZLSJFNQ-RWOPYEJCSA-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: | 3672-15-9 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| IUPAC Name: | (3,4,5,6-tetrahydroxyoxan-2-yl)methyl phosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Traditional IUPAC Name: | (3,4,5,6-tetrahydroxyoxan-2-yl)methyl 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 |
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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 + D-Mannose > Mannose 6-phosphate + Pyruvic acid Water + 2(alpha-D-Mannosyl-6-phosphate)-D-glycerate > Glyceric acid + Mannose 6-phosphate Water + Mannose 6-phosphate > D-Mannose + Phosphate Mannose 6-phosphate <> Fructose 6-phosphate D-Mannose 1-phosphate <> Mannose 6-phosphate Mannose 6-phosphate <> D-Mannose 1-phosphate Mannose 6-phosphate <> beta-D-Fructose 6-phosphate Protein N(pi)-phospho-L-histidine + D-Mannose <> Protein histidine + Mannose 6-phosphate D-Mannose + Adenosine triphosphate > Hydrogen ion + Mannose 6-phosphate + ADP D-Mannose + Phosphoenolpyruvic acid > Mannose 6-phosphate + Pyruvic acid Mannose 6-phosphate > Fructose 6-phosphate Alpha-D-mannose 1-phosphate > Mannose 6-phosphate 2-O-(6-Phospho-alpha-D-mannosyl)-D-glycerate + Water > Mannose 6-phosphate + Glyceric acid 2(alpha-D-Mannosyl-6-phosphate)-D-glycerate + Water <> Mannose 6-phosphate + Glyceric acid α-D-glucose 6-phosphate + Mannose 6-phosphate > α-D-glucose 1-phosphate α-D-glucose 6-phosphate + Mannose 6-phosphate > Alpha-D-glucose 1-phosphate alpha-D-Glucose + HPr - phosphorylated > α-D-glucose 6-phosphate + HPr + Mannose 6-phosphate UDP-Glucose + Mannose 6-phosphate > alpha,alpha-Trehalose 6-phosphate + Uridine 5'-diphosphate + Hydrogen ion | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| 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: | Pascual, C.; Herrera, L. Use of permeabilized yeast cells as a system of enzyme immobilization. Its use for the preparation of mannose 6-phosphate. Folia Microbiologica (Prague, Czech Republic) (1981), 26(2), 103-6. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Material Safety Data Sheet (MSDS) | Download (PDF) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Links: |
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Enzymes
- General function:
- Involved in mannose-6-phosphate isomerase activity
- Specific function:
- Involved in the conversion of glucose to GDP-L-fucose, which can be converted to L-fucose, a capsular polysaccharide
- Gene Name:
- manA
- Uniprot ID:
- P00946
- Molecular weight:
- 42850
Reactions
| D-mannose 6-phosphate = D-fructose 6-phosphate. |
- 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 intramolecular transferase activity, phosphotransferases
- Specific function:
- Involved in the biosynthesis of the capsular polysaccharide colanic acid
- Gene Name:
- manB
- Uniprot ID:
- P24175
- Molecular weight:
- 50462
Reactions
| Alpha-D-mannose 1-phosphate = D-mannose 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 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 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. This system is involved in mannose transport
- Gene Name:
- manX
- Uniprot ID:
- P69797
- Molecular weight:
- 35047
Reactions
| Protein EIIA N(pi)-phospho-L-histidine + protein EIIB = protein EIIA + protein EIIB N(pi)-phospho-L-histidine/cysteine. |
| Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate. |
- General function:
- Involved in catalytic activity
- Specific function:
- Catalyzes the hydrolysis of sugar phosphate to sugar and inorganic phosphate. Has a wide substrate specificity catalyzing the hydrolysis of fructose-1-P most efficiently, but it remains uncertain if this is the real substrate in vivo
- Gene Name:
- supH
- Uniprot ID:
- P75792
- Molecular weight:
- 30413
Reactions
| Sugar phosphate + H(2)O = 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 mannose transport
- Gene Name:
- manY
- Uniprot ID:
- P69801
- Molecular weight:
- 27636
- 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 mannose transport
- Gene Name:
- manZ
- Uniprot ID:
- P69805
- Molecular weight:
- 31303
- General function:
- Involved in catalytic activity
- Specific function:
- May hydrolyze mannosyl-D-glycerate to mannose-6- phosphate and glycerate
- Gene Name:
- mngB
- Uniprot ID:
- P54746
- Molecular weight:
- 100014
Reactions
| 2-O-(6-phospho-alpha-D-mannosyl)-D-glycerate + H(2)O = D-mannose 6-phosphate + D-glycerate. |
- 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 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 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 mannose transport
- Gene Name:
- manY
- Uniprot ID:
- P69801
- Molecular weight:
- 27636
- 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 mannose transport
- Gene Name:
- manZ
- Uniprot ID:
- P69805
- Molecular weight:
- 31303
- 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 transmembrane transport
- Specific function:
- Transport protein for sugar phosphate uptake
- Gene Name:
- uhpT
- Uniprot ID:
- P0AGC0
- Molecular weight:
- 50606
- 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