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N-Acetylmannosamine (ECMDB01129) (M2MDB000266)
Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 13:45:54 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-10-15 16:13:51 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | N-Acetylmannosamine | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | N-Acetylmannosamine is a monosaccharide that is used as a precursor in the chemical or enzymatic synthesis of the neuraminic acids found in glycolipids and glycoproteins. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C8H15NO6 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 221.2078 Monoisotopic: 221.089937217 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | OVRNDRQMDRJTHS-OZRXBMAMSA-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-/m1/s1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | 3615-17-6 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | N-[(3S,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]ethanimidic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | N-acetylmannosamine | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | [H][C@@]1(O)O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1NC(C)=O | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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 |
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Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | Phosphoenolpyruvic acid + N-Acetylmannosamine > N-Acetyl-D-mannosamine 6-phosphate + Pyruvic acid N-Acetylmannosamine + Adenosine triphosphate > N-Acetyl-D-mannosamine 6-phosphate + ADP + Hydrogen ion N-Acetylneuraminic acid + N-acetylneuraminate <> N-Acetylmannosamine + Pyruvic acid Uridine diphosphate-N-acetylglucosamine + Water <> N-Acetylmannosamine + Uridine 5'-diphosphate N-Acetylneuraminic acid <> N-Acetylmannosamine + Pyruvic acid Adenosine triphosphate + N-Acetylmannosamine <> ADP + N-Acetyl-D-mannosamine 6-phosphate N-Acetylmannosamine + Phosphate <> N-Acetyl-D-mannosamine 6-phosphate + Water N-Acetylmannosamine + Phosphoenolpyruvic acid > N-Acetyl-D-mannosamine 6-phosphate + Pyruvic acid N-acetylneuraminate > N-Acetylmannosamine + Pyruvic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMPDB Pathways: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
KEGG Pathways: |
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EcoCyc Pathways: |
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Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
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Synthesis Reference: | Satoh, Chiyoko; Akio, Kiyomoto. Nitrogen-containing sugars. I. Synthesis of 2-acetamido-2-deoxy-D-mannose from 1-deoxy-1-nitro-D-mannitol pentaacetate. Chemical & Pharmaceutical Bulletin (1964), 12(5), 615-19. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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 catalytic activity
- Specific function:
- Catalyzes the cleavage of N-acetylneuraminic acid (sialic acid) to form pyruvate and N-acetylmannosamine via a Schiff base intermediate
- Gene Name:
- nanA
- Uniprot ID:
- P0A6L4
- Molecular weight:
- 32593
Reactions
N-acetylneuraminate = N-acetyl-D-mannosamine + pyruvate. |
- General function:
- Involved in UDP-N-acetylglucosamine 2-epimerase activity
- Specific function:
- Catalyzes the reversible epimerization at C-2 of UDP-N- acetylglucosamine (UDP-GlcNAc) and thereby provides bacteria with UDP-N-acetylmannosamine (UDP-ManNAc), the activated donor of ManNAc residues. Also involved in bacteriophage N4 adsorption
- Gene Name:
- wecB
- Uniprot ID:
- P27828
- Molecular weight:
- 42244
Reactions
UDP-N-acetyl-D-glucosamine = UDP-N-acetyl-D-mannosamine. |
- General function:
- Involved in ATP binding
- Specific function:
- Catalyzes the phosphorylation of N-acetylmannosamine (ManNAc) to ManNAc-6-P. Has also low level glucokinase activity in vitro
- Gene Name:
- nanK
- Uniprot ID:
- P45425
- Molecular weight:
- 29644
Reactions
ATP + N-acyl-D-mannosamine = ADP + N-acyl-D-mannosamine 6-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 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 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. |
- General function:
- Not Available
- Specific function:
- Not Available
- Gene Name:
- yniC
- Uniprot ID:
- P77247
- Molecular weight:
- Not Available
- General function:
- Not Available
- Specific function:
- Not Available
- Gene Name:
- yfbT
- Uniprot ID:
- P77625
- Molecular weight:
- Not Available
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 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 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