N-Acetyl-D-glucosamine (ECMDB00215) (M2MDB000088)
| Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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| Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Creation Date | 2012-05-31 10:23:52 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Update Date | 2015-09-13 12:56:07 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Secondary Accession Numbers |
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| Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Name: | N-Acetyl-D-glucosamine | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | N-Acetyl-D-Glucosamine (N-acetlyglucosamine) is a monosaccharide derivative of glucose. Chemically it is an amide between glucosamine and acetic acid. A single N-acetlyglucosamine moiety linked to serine or threonine residues on nuclear and cytoplasmic proteins -O-GlcNAc, is an ubiquitous post-translational protein modification. O-GlcNAc modified proteins are involved in sensing the nutrient status of the surrounding cellular environment and adjusting the activity of cellular proteins accordingly. O-GlcNAc initiates a protective response to stress, modulates a cell's capacity to grow and divide, and regulates gene transcription. (PMID 16237703) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Structure |  | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synonyms: |
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| Chemical Formula: | C8H15NO6 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Weight: | Average: 221.2078 Monoisotopic: 221.089937217 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI Key: | OVRNDRQMDRJTHS-DMHSOCPYSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI: | InChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6-,7-,8+/m0/s1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| CAS number: | 7512-17-6 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| IUPAC Name: | N-[(2R,3S,4S,5R,6S)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Traditional IUPAC Name: | N-[(2R,3S,4S,5R,6S)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMILES: | [H]OC([H])([H])[C@]1([H])O[C@@]([H])(O[H])[C@@]([H])(N([H])C(=O)C([H])([H])[H])[C@]([H])(O[H])[C@@]1([H])O[H] | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| 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 |
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| Molecular Framework | Aliphatic heteromonocyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Descriptors | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Charge: | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Melting point: | 210 °C | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Experimental Properties: |
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| Predicted Properties |
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| Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Reactions: | Phosphoenolpyruvic acid + N-Acetyl-D-glucosamine > N-Acetyl-D-Glucosamine 6-Phosphate + Pyruvic acid N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramic acid + Water > N-Acetyl-D-glucosamine + 1,6-Anhydro-N-acetylmuramate N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tetrapeptide + Water > N-Acetyl-D-glucosamine + 1,6-Anhydrous-N-Acetylmuramyl-tetrapeptide N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tripeptide + Water > N-Acetyl-D-glucosamine + 1,6-Anhydrous-N-Acetylmuramyl-tripeptide 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 Chitobiose + Water <>2 N-Acetyl-D-glucosamine Adenosine triphosphate + N-Acetyl-D-glucosamine <> ADP + N-Acetyl-D-Glucosamine 6-Phosphate Chitin + Water <> N-Acetyl-D-glucosamine + Chitin Protein N(pi)-phospho-L-histidine + N-Acetyl-D-glucosamine <> Protein histidine + N-Acetyl-D-Glucosamine 6-Phosphate a peptidoglycan + Water a peptidoglycan with cleaved N-acetyl-glucosamine + N-Acetyl-D-glucosamine N-Acetyl-D-glucosamine + Adenosine triphosphate > Hydrogen ion + N-Acetyl-D-Glucosamine 6-Phosphate + ADP <i>N</i>-acetyl-β-D-glucosamine(anhydrous)-<i>N</i>-acetylmuramate + Water N-Acetyl-D-glucosamine + 1,6-Anhydro-N-acetylmuramate Phosphoenolpyruvic acid + N-Acetyl-D-glucosamine > N-Acetyl-D-Glucosamine 6-Phosphate + Pyruvic acid Adenosine triphosphate + Water + N-Acetyl-D-glucosamine > N-Acetyl-D-glucosamine + ADP + Phosphate + Hydrogen ion Adenosine triphosphate + Water + N-Acetyl-D-glucosamine > N-Acetyl-D-glucosamine + ADP + Phosphate + Hydrogen ion Chitobiose + Water <>2 N-Acetyl-D-glucosamine Chitobiose + Water <>2 N-Acetyl-D-glucosamine | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMPDB Pathways: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| KEGG Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| EcoCyc Pathways: |
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| Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References: |
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| Synthesis Reference: | Zhang, He; Qi, Shanlong; Yang, Shenggui. Production of N-acetyl-D-glucosamine from chitin. Faming Zhuanli Shenqing Gongkai Shuomingshu (2006), 6pp. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Material Safety Data Sheet (MSDS) | Download (PDF) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| 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 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 hydrolase activity, hydrolyzing O-glycosyl compounds
- Specific function:
- Bifunctional enzyme with lysozyme/chitinase activity
- Gene Name:
- chiA
- Uniprot ID:
- P13656
- Molecular weight:
- 97057
Reactions
| Random hydrolysis of N-acetyl-beta-D-glucosaminide (1->4)-beta-linkages in chitin and chitodextrins. |
| Hydrolysis of (1->4)-beta-linkages between N-acetylmuramic acid and N-acetyl-D-glucosamine residues in a peptidoglycan and between N-acetyl-D-glucosamine residues in chitodextrins. |
- 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 beta-N-acetylhexosaminidase activity
- Specific function:
- Cleaves GlcNAc linked beta-1,4 to MurNAc tripeptides
- Gene Name:
- nagZ
- Uniprot ID:
- P75949
- Molecular weight:
- 37594
Reactions
| Hydrolysis of terminal non-reducing N-acetyl-D-hexosamine residues in N-acetyl-beta-D-hexosaminides. |
- 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 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 hydrolase activity, hydrolyzing O-glycosyl compounds
- Specific function:
- Bifunctional enzyme with lysozyme/chitinase activity
- Gene Name:
- chiA
- Uniprot ID:
- P13656
- Molecular weight:
- 97057
Reactions
| Random hydrolysis of N-acetyl-beta-D-glucosaminide (1->4)-beta-linkages in chitin and chitodextrins. |
| Hydrolysis of (1->4)-beta-linkages between N-acetylmuramic acid and N-acetyl-D-glucosamine residues in a peptidoglycan and between N-acetyl-D-glucosamine residues in chitodextrins. |
- 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 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