N-Acetylaspartylglutamic acid

N-Acetylaspartylglutamic acid
Stereo, skeletal formula of N-acetylaspartylglutamic acid
Names
Systematic IUPAC name
(2S)-2-[(2S)-2-Acetamido-3-carboxypropanamido]pentanedioic acid
Other names
  • N-Acetyl-L-α-aspartyl-L-glutamic acid
  • N-Acetyl-1-aspartylglutamic acid[citation needed]
  • Isospaglumic acid
  • Spaglumic acid[1][2]
Identifiers
3D model (JSmol)
Abbreviations NAAG
ChemSpider
ECHA InfoCard 100.163.604 Edit this at Wikidata
MeSH N-acetyl-1-aspartylglutamic+acid
UNII
  • InChI=1S/C11H16N2O8/c1-5(14)12-7(4-9(17)18)10(19)13-6(11(20)21)2-3-8(15)16/h6-7H,2-4H2,1H3,(H,12,14)(H,13,19)(H,15,16)(H,17,18)(H,20,21)/t6-,7-/m0/s1 checkY
    Key: OPVPGKGADVGKTG-BQBZGAKWSA-N checkY
  • CC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(O)=O
Properties
C11H16N2O8
Molar mass 304.255 g·mol−1
Pharmacology
R01AC05 (WHO) S01GX03 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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N-Acetylaspartylglutamic acid (N-acetylaspartylglutamate or NAAG) is a peptide neurotransmitter and the third-most-prevalent neurotransmitter in the mammalian nervous system. NAAG consists of N-acetylaspartic acid (NAA) and glutamic acid coupled via a peptide bond.

NAAG was discovered as a nervous system-specific peptide in 1965 by Curatolo and colleagues[3] but initially disregarded as a neurotransmitter and not extensively studied. However it meets the criteria for a neurotransmitter, including being concentrated in neurons, packed in synaptic vesicles, released in a calcium-dependent manner, and hydrolyzed in the synaptic space by enzymatic activity.

NAAG activates a specific receptor, the metabotropic glutamate receptor type 3. It is synthesized enzymatically from its two precursors and catabolized by NAAG peptidases in the synapse. The inhibition of the latter enzymes has potentially important therapeutic effects in animal models of several neurologic conditions and disorders.

Under the INN spaglumic acid,[1][2] NAAG is used as an antiallergic medication in eye drops and nasal preparations.

  1. ^ a b Spaglumic Acid, drugs.com
  2. ^ a b This is a misnomer: "spaglumic acid" is the β-aspartyl isomer whereas "isospaglumic acid" is the α-aspartyl isomer. See PubChem entry for "spaglumic acid".
  3. ^ CURATOLO A, D ARCANGELO P, LINO A, BRANCATI A (1965). "Distribution Of N-Acetyl-Aspartic And N-Acetyl-Aspartyl-Glutamic Acids In Nervous Tissue". J. Neurochem. 12 (4): 339–42. doi:10.1111/j.1471-4159.1965.tb06771.x. PMID 14340686. S2CID 29248053.