N-Acetyl-D-Glucosamine 6-Phosphate (ECMDB01062) (M2MDB000238)
| Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Creation Date | 2012-05-31 13:44:21 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Update Date | 2015-06-03 15:53:41 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Secondary Accession Numbers |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Name: | N-Acetyl-D-Glucosamine 6-Phosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | N-Acetyl-D-Glucosamine 6-Phosphate is an intermediate in the metabolism of Aminosugars. It is a substrate for Glucosamine 6-phosphate N-acetyltransferase. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Structure |  | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synonyms: |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Chemical Formula: | C8H16NO9P | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Weight: | Average: 301.1877 Monoisotopic: 301.056267627 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI Key: | BRGMHAYQAZFZDJ-RTRLPJTCSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI: | InChI=1S/C8H16NO9P/c1-3(10)9-5-7(12)6(11)4(18-8(5)13)2-17-19(14,15)16/h4-8,11-13H,2H2,1H3,(H,9,10)(H2,14,15,16)/t4-,5-,6-,7-,8?/m1/s1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| CAS number: | 102029-88-9 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| IUPAC Name: | {[(2R,3S,4R,5R)-5-acetamido-3,4,6-trihydroxyoxan-2-yl]methoxy}phosphonic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Traditional IUPAC Name: | [(2R,3S,4R,5R)-5-acetamido-3,4,6-trihydroxyoxan-2-yl]methoxyphosphonic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMILES: | CC(=O)N[C@H]1C(O)O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Super Class | Organic oxygen compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Class | Organooxygen compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Sub Class | Carbohydrates and carbohydrate conjugates | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Direct Parent | Acylaminosugars | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| 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: | Phosphoenolpyruvic acid + N-Acetyl-D-glucosamine > N-Acetyl-D-Glucosamine 6-Phosphate + Pyruvic acid N-Acetyl-D-Glucosamine 6-Phosphate + Water <> Acetic acid + Glucosamine 6-phosphate N-Acetyl-D-glucosamine + Adenosine triphosphate <> N-Acetyl-D-Glucosamine 6-Phosphate + ADP + Hydrogen ion Diacetylchitobiose-6-phosphate + Water > N-Acetyl-D-glucosamine + N-Acetyl-D-Glucosamine 6-Phosphate N-Acetylmuramic acid 6-phosphate + Water <> N-Acetyl-D-Glucosamine 6-Phosphate + D-Lactic acid N-Acetyl-D-mannosamine 6-phosphate <> N-Acetyl-D-Glucosamine 6-Phosphate Adenosine triphosphate + N-Acetyl-D-glucosamine <> ADP + N-Acetyl-D-Glucosamine 6-Phosphate N-Acetyl-D-Glucosamine 6-Phosphate <> N-Acetyl-D-mannosamine 6-phosphate Protein N(pi)-phospho-L-histidine + N-Acetyl-D-glucosamine <> Protein histidine + N-Acetyl-D-Glucosamine 6-Phosphate N-Acetyl-D-glucosamine + Adenosine triphosphate > Hydrogen ion + N-Acetyl-D-Glucosamine 6-Phosphate + ADP Water + N-Acetyl-D-Glucosamine 6-Phosphate > Glucosamine 6-phosphate + Acetic acid Phosphoenolpyruvic acid + N-Acetyl-D-glucosamine > N-Acetyl-D-Glucosamine 6-Phosphate + Pyruvic acid N-Acetylmuramic acid 6-phosphate + Water > N-Acetyl-D-Glucosamine 6-Phosphate + D-Lactic acid N-Acetyl-D-Glucosamine 6-Phosphate + Water > D-glucosamine 6-phosphate + Acetic acid Adenosine triphosphate + N-Acetylglucosamine > ADP + N-Acetyl-D-Glucosamine 6-Phosphate N-Acetyl-D-Glucosamine 6-Phosphate + Water + N-Acetyl-D-Glucosamine 6-Phosphate > Acetic acid + Glucosamine 6-phosphate N-Acetyl-D-glucosamine + Adenosine triphosphate + N-Acetylglucosamine > N-Acetyl-D-Glucosamine 6-Phosphate + Adenosine diphosphate + Hydrogen ion + N-Acetyl-D-Glucosamine 6-Phosphate + ADP N-Acetyl-D-glucosamine + HPr - phosphorylated + N-Acetylglucosamine > N-Acetyl-D-Glucosamine 6-Phosphate + HPr + N-Acetyl-D-Glucosamine 6-Phosphate N'-monoacetylchitobiose-6'-phosphate + Water > N-Acetyl-D-Glucosamine 6-Phosphate + Glucosamine N-Acetylmuramate 6-phosphate + Water <> N-Acetyl-D-Glucosamine 6-Phosphate + D-Lactic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| 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 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 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 N-acetylglucosamine transport
- Gene Name:
- nagE
- Uniprot ID:
- P09323
- Molecular weight:
- 68346
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:
- Converts N-acetylmannosamine-6-phosphate (ManNAc-6-P) to N-acetylglucosamine-6-phosphate (GlcNAc-6-P) (Potential)
- Gene Name:
- nanE
- Uniprot ID:
- P0A761
- Molecular weight:
- 24073
Reactions
| N-acyl-D-glucosamine 6-phosphate = N-acyl-D-mannosamine 6-phosphate. |
- General function:
- Involved in hydrolase activity
- Specific function:
- N-acetyl-D-glucosamine 6-phosphate + H(2)O = D-glucosamine 6-phosphate + acetate
- Gene Name:
- nagA
- Uniprot ID:
- P0AF18
- Molecular weight:
- 40949
Reactions
| N-acetyl-D-glucosamine 6-phosphate + H(2)O = D-glucosamine 6-phosphate + acetate. |
- 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 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 N-acetylglucosamine kinase activity
- Specific function:
- Catalyzes the phosphorylation of N-acetyl-D-glucosamine (GlcNAc) derived from cell-wall degradation, yielding GlcNAc-6-P. Has also low level glucokinase activity in vitro
- Gene Name:
- nagK
- Uniprot ID:
- P75959
- Molecular weight:
- 33042
Reactions
| ATP + N-acetyl-D-glucosamine = ADP + N-acetyl-D-glucosamine 6-phosphate. |
- General function:
- Involved in carbon-oxygen lyase activity
- Specific function:
- Specifically catalyzes the cleavage of the D-lactyl ether substituent of MurNAc 6-phosphate, producing GlcNAc 6- phosphate and D-lactate. Is required for growth on MurNAc as the sole source of carbon and energy. Together with AnmK, is also required for the utilization of anhydro-N-acetylmuramic acid (anhMurNAc) either imported from the medium or derived from its own cell wall murein, and thus plays a role in cell wall recycling
- Gene Name:
- murQ
- Uniprot ID:
- P76535
- Molecular weight:
- 31220
Reactions
| N-acetylmuramate 6-phosphate + H(2)O = N-acetyl-D-glucosamine 6-phosphate + D-lactate. |
- 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 N-acetylglucosamine transport
- Gene Name:
- nagE
- Uniprot ID:
- P09323
- Molecular weight:
- 68346
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 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. |