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Acetylaspartic acid

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Acetylaspartic acid

N-Acetylaspartic acid
Stereo, skeletal formula of N-acetylaspartic acid (S)
Names
IUPAC name
2-Acetamidobutanedioic acid[1]
Identifiers
 N
S YesY
3DMet
1726198 S
ChEBI  YesY
ChEMBL  N
ChemSpider  N
R YesY
EC number 219-827-5
Jmol-3D images Image
Image
KEGG  N
MeSH
PubChem
 R
 S
RTECS number CI9098600
Properties
C6H9NO5
Molar mass 175.14 g·mol−1
Appearance Colourless, transparent crystals
Melting point 137 to 140 °C (279 to 284 °F; 410 to 413 K)
Boiling point 141 to 144 °C (286 to 291 °F; 414 to 417 K)
log P −2.209
Acidity (pKa) 3.142
Basicity (pKb) 10.855
Hazards
S-phrases S22, S24/25
Related compounds
Related alkanoic acids
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 N  (: YesY/N?)

N-Acetylaspartic acid, or N-acetylaspartate (NAA), is a derivative of aspartic acid with a formula of C6H9NO5 and a molecular weight of 175.139.

NAA is the second-most-concentrated molecule in the brain after the amino acid glutamate. It is detected in the adult brain in neurons,[2] oligodendrocytes, and myelin[3] and is synthesized in the mitochondria from the amino acid aspartic acid and acetyl-coenzyme A.[4] The various functions served by NAA are still under investigation, but the primary proposed functions include its being:

  1. A neuronal osmolyte that is involved in fluid balance in the brain
  2. A source of acetate for lipid and myelin synthesis in oligodendrocytes, the glial cells that myelinate neuronal axons
  3. A precursor for the synthesis of the important neuronal dipeptide N-Acetylaspartylglutamate
  4. A contributor to energy production from the amino acid glutamate in neuronal mitochondria.

In the brain, NAA is thought to be present predominantly in neuronal cell bodies, where it acts as a neuronal marker.[5] However, the recent discovery of a higher concentration of NAA in myelin and oligodendrocytes than in neurons raises questions about the validity of the use of NAA as a neuronal marker.[3] 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.

NAA may also be a marker of creativity.[6] It has also been demonstrated that high NAA level in hippocampus is related to better working memory performance in humans.[7]

NAA may function as a neurotransmitter in the brain by acting on metabotropic glutamate receptors.[8]

See also

References

  1. ^
  2. ^
  3. ^ a b
  4. ^ Patel, T. B. and J. B. Clark (1979). "Synthesis of N-acetyl-L-aspartate by rat brain mitochondria and its involvement in mitochondrial/cytosolic carbon transport." Biochem J 184(3): 539-46. http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&dopt=Citation&list_uids=1754068
  5. ^
  6. ^ http://www.newscientist.com/article/mg20227084.300-creativity-chemical-favours-the-smart.html
  7. ^ Kozlovskiy, S, Vartanov, A, Pyasik, M, Polikanova, I. (2012). "Working memory and N-acetylaspartate level in hippocampus, parietal cortex and subventricular zone". International Journal of Psychology, vol. 47. P. 584. doi:10.1080/00207594.2012.709117
  8. ^
  • N-Acetylaspartate: A Unique Neuronal Molecule in the Central Nervous System, eds., J.R.Moffett, S.B.Tieman, D.R.Weinberger, J.T.Coyle, and M.A.Namboodiri, pp. 7–26. New York, NY: Springer Science + Business Media, 2006.
  • Biochemical Support for the "Threshold" Theory of Creativity: A Magnetic Resonance Spectroscopy Study, Rex E. Jung et al., April 22, 2009, 29(16):5319-5325; doi:10.1523/JNEUROSCI.0588-09.2009

External links

  • GeneReviews/NCBI/UW/NIH entry on Canavan disease
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