N-Acetylaspartic acid

N-Acetylaspartic acid

Names
IUPAC name 2-Acetamidobutanedioic acid[1]
Identifiers
CAS Number	2545-40-6 997-55-7 S
3D model (Jmol)	Interactive image Interactive image
3DMet	B00227
Beilstein Reference	1726198 S
ChEBI	CHEBI:21547
ChEMBL	ChEMBL1162493
ChemSpider	88007 677387 R
ECHA InfoCard	100.012.403
EC Number	219-827-5
KEGG	C01042
MeSH	N-acetylaspartate
PubChem	97508 774916 R 65065 S
RTECS number	CI9098600
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) Key: OTCCIMWXFLJLIA-UHFFFAOYSA-N
SMILES Cc(:[o]):[nH]C(Cc(:[o]):[oH])c(:[o]):[oH] CC(=O)NC(CC(O)=O)C(O)=O
Properties
Chemical formula	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	3-Ureidopropionic acid beta-Ureidoisobutyric acid Carbamoyl aspartic acid Aceglutamide N-Acetylglutamic acid Citrulline
Related compounds	Bromisoval Carbromal
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 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]

Function

The various functions served by NAA are under investigation, but the primary proposed functions include:

• Neuronal osmolyte that is involved in fluid balance in the brain
• Source of acetate for lipid and myelin synthesis in oligodendrocytes, the glial cells that myelinate neuronal axons
• Precursor for the synthesis of the neuronal dipeptide N-Acetylaspartylglutamate
• 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]

Applications

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. 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 potential diagnostic molecule for doctors treating patients with brain damage or disease.

NAA may be a marker of creativity.^[6] High NAA levels in the hippocampus are 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

• Aspartoacylase
• Canavan disease

References

1. "N-acetylaspartate - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 8 January 2012.
2. Simmons, ML; Frondoza, CG; Coyle, JT (1991). "Immunocytochemical localization of N-acetyl-aspartate with monoclonal antibodies.". Neuroscience. 45 (1): 37–45. doi:10.1016/0306-4522(91)90101-s. PMID 1754068.
3. Nordengen, K; Heuser, C; Rinholm, JE; Matalon, R; Gundersen, V (2015). "Localisation of N-acetylaspartate in oligodendrocytes/myelin.". Brain Struct Funct. 220 (2): 899–917. doi:10.1007/s00429-013-0691-7. PMID 24379086.
4. Patel, T. B.; Clark, J. B. (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. PMC 1161835. PMID 540047.
5. Chatham JC, Blackband SJ (2001). "Nuclear magnetic resonance spectroscopy and imaging in animal research.". ILAR J. 42 (3): 189–208. doi:10.1093/ilar.42.3.189. PMID 11406719.
6. Geddes, Linda. "Creativity chemical favours the smart".
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. 47: 584. doi:10.1080/00207594.2012.709117.
8. Yan, Hai-Dun; Ishihara, Kumatoshi; Serikawa, Tadao; Sasa, Masashi (2003-09-01). "Activation by N-Acetyl-l-Aspartate of Acutely Dissociated Hippocampal Neurons in Rats via Metabotropic Glutamate Receptors". Epilepsia. 44 (9): 1153–1159. doi:10.1046/j.1528-1157.2003.49402.x. ISSN 1528-1167.

Further information

• Moffett, John; Tieman, Suzannah B.; Weinberger, Daniel R.; Coyle, Joseph T.; Namboodiri, Aryan M. A., eds. (21 October 2006). N-Acetylaspartate: A Unique Neuronal Molecule in the Central Nervous System. Springer Science & Business Media. ISBN 978-0-387-30172-3.
• 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