N-Acetylaspartic acid

N-Acetylaspartic acid
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 Y
PubChem	65065
ChemSpider	58576 Y
EC number	213-643-9
MeSH	N-acetylaspartate
RTECS number	CI9098600
Jmol-3D images	Image 1
SMILES CC(=O)N[C@@H](CC(=O)O)C(=O)O
InChI InChI=1S/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 Y Key: OTCCIMWXFLJLIA-BYPYZUCNSA-N Y 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 Key: OTCCIMWXFLJLIA-BYPYZUCNBM
Properties
Molecular formula	C6H9NO5
Molar mass	175.139 g/mol
Melting point	137-140 °C
Hazards
S-phrases	S22 S24/25
Y acid (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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 synthesized in neurons from the amino acid aspartic acid and acetyl-coenzyme A. 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 ^[1]. 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.^[2]

See also

• Aspartoacylase
• Canavan disease

References

• 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.

http://www.n-acetylaspartate.com

Finds correlations between measure of creativity and fMRIs of NAA levels in areas of brain: 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

1. ^ Chatham JC, Blackband SJ. (2001). "Nuclear magnetic resonance spectroscopy and imaging in animal research.". ILAR J 42 (3): 189–208. PMID 11406719. 
2. ^ http://www.newscientist.com/article/mg20227084.300-creativity-chemical-favours-the-smart.html

External links

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