N-Acetylaspartate
From Wikipedia, the free encyclopedia
| N-Acetylaspartate | |
|---|---|
 |
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| IUPAC name | (2S)-2-Acetamidobutanedioic acid |
| Other names | Acetylaspartic acid N-Acetylaspartic acid N-Acetyl-L-aspartate Acetyl-L-aspartic acid N-Acetyl-L-aspartic acid |
| Identifiers | |
| Abbreviations | NAA |
| CAS number | [997-55-7] |
| PubChem | |
| EINECS number | |
| MeSH | |
| RTECS number | CI9098600 |
| SMILES | CC(=O)N[C@@H](CC(=O)O)C(=O)O |
| InChI | 1/C6H9NO5/c1-3(8)7-4(6(11)12)2-5(9)10 /h4H,2H2,1H3,(H,7,8)(H,9,10) (H,11,12)/t4-/m0/s1/f/h7,9,11H |
| Properties | |
| Molecular formula | C6H9NO5 |
| Molar mass | 175.139 g/mol |
| Melting point |
137-140 °C |
| Hazards | |
| S-phrases | S22 S24/25 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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N-Acetylaspartate (NAA), or N-acetylaspartic acid, is a derivative of aspartic acid with a formula of C6H9NO5 and a molecular weight of 175.139.
NAA is the most concentrated molecule in the brain after the amino acid glutamate. NAA is synthesized in neurons from the amino acid aspartate and acetyl-coenzyme A. The various functions served by NAA are still under investigation, but the primary proposed functions include its being:
- A neuronal osmolyte that is involved in fluid balance in the brain
- A source of acetate for lipid and myelin synthesis in oligodendrocytes, the glial cells that myelinate neuronal axons
- A precursor for the synthesis of the important neuronal dipeptide N-Acetylaspartylglutamate
- A contributor to energy production from the amino acid glutamate in neuronal mitochondria.
NAA gives off the largest signal in magnetic resonance spectroscopy of the human brain, and the levels measured there are decreased in numerous neuropathological conditions ranging from brain injury to stroke to Alzheimer's disease. This fact makes NAA a reliable diagnostic molecule for doctors treating patients with brain damage or disease.
