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Chemical Compound Review

CPD-302     (2R)-2-azaniumylbutanedioate

Synonyms: CHEBI:29990, AC1NUT1X, ZINC00895218, A833401, D-aspartate(1-), ...
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Disease relevance of L-aspartic acid


Psychiatry related information on L-aspartic acid


High impact information on L-aspartic acid

  • The NMDA (N-methyl D-aspartate) receptors in the brain play a critical role in synaptic plasticity, synaptogenesis and excitotoxicity [11].
  • The rate constant for D-aspartate formation in the brain is equal to the predicted value calculated for 37 degrees C. Accumulation of the uncommon D-aspartate isomer in myelinated white matter implies that there is little or no turnover of this tissue, and this may have a bearing on dysfunction of the aging brain or on other diseases of myelin [12].
  • Autoradiography demonstrated prominent retrograde labeling of olivocerebellar climbing fiber neurons after injection of tritiated D-aspartate into the rat cerebellar cortex or deep nuclei [13].
  • Elastin purified by a new technique from normal lung parenchyma was hydrolyzed; then the prevalences of D-aspartate and 14C were measured by gas chromatography and accelerator-mass spectrometry, respectively [14].
  • Marked longevity of human lung parenchymal elastic fibers deduced from prevalence of D-aspartate and nuclear weapons-related radiocarbon [14].

Chemical compound and disease context of L-aspartic acid


Biological context of L-aspartic acid

  • Experiments with a range of acidic amino acid analogues indicated that the ligand selectivities of these two binding sites conformed to those of the N-methyl D-aspartate and quisqualate receptor classes defined electrophysiologically [20].
  • Differences in the macroscopic kinetics of channels activated by concentration jumps of L-glutamate or D-aspartate were correlated with differences in uptake kinetics, indicating a close correspondence of channel gating to state transitions in the transporter cycle [21].
  • Exocytosis of D-aspartate further supports the role(s) of D-aspartate as a chemical transmitter in neuroendocrine cells [2].
  • The murine N-methyl D-aspartate receptor subunit NR2C (epsilon-3) is encoded by a unique gene composed of 12 translated and three 5'-untranslated exons that spread over approximately 20 kilobases of genomic sequence [22].
  • Neither L-A beta HA nor DL-AP3 blocked PI hydrolysis stimulated by D-aspartate in hippocampus.(ABSTRACT TRUNCATED AT 250 WORDS)[23]

Anatomical context of L-aspartic acid


Associations of L-aspartic acid with other chemical compounds


Gene context of L-aspartic acid

  • Autophosphorylation-dependent targeting of calcium/ calmodulin-dependent protein kinase II by the NR2B subunit of the N-methyl- D-aspartate receptor [28].
  • The glutamate receptor, ionotropic, N-methyl D-aspartate 2A (GRIN2A) gene that encodes the 2A subunit of the NMDA receptor, resides in this region and a recent study has reported an association between this gene and ADHD [7].
  • Recent studies have demonstrated that mice lacking protein L-isoaspartate (D-aspartate) O-methyltransferase (Pcmt1-/- mice) have alterations in the insulin-like growth factor-I (IGF-I) and insulin receptor pathways within the hippocampal formation as well as other brain regions [29].
  • The protein L-isoaspartate (D-aspartate) O-methyltransferase (PCMT1) can initiate the repair of age-damaged aspartyl and asparaginyl residues of intracellular proteins [30].
  • The functionality of the C-terminus (Ser-Asn-Leu; SNL) of human d-aspartate oxidase, an enzyme proposed to have a role in the inactivation of synaptically released d-aspartate, as a peroxisome-targeting signal (PTS1) was investigated in vivo and in vitro [31].

Analytical, diagnostic and therapeutic context of L-aspartic acid


  1. A femtomolar-acting neuroprotective peptide. Brenneman, D.E., Gozes, I. J. Clin. Invest. (1996) [Pubmed]
  2. D-Aspartate is stored in secretory granules and released through a Ca(2+)-dependent pathway in a subset of rat pheochromocytoma PC12 cells. Nakatsuka, S., Hayashi, M., Muroyama, A., Otsuka, M., Kozaki, S., Yamada, H., Moriyama, Y. J. Biol. Chem. (2001) [Pubmed]
  3. Aslfm, the D-Aspartate Ligase Responsible for the Addition of D-Aspartic Acid onto the Peptidoglycan Precursor of Enterococcus faecium. Bellais, S., Arthur, M., Dubost, L., Hugonnet, J.E., Gutmann, L., van Heijenoort, J., Legrand, R., Brouard, J.P., Rice, L., Mainardi, J.L. J. Biol. Chem. (2006) [Pubmed]
  4. Biologically active MK-801 and SKF-10,047 binding sites distinct from those in rat brain are expressed on human lung cancer cells. Maneckjee, R., Minna, J.D. Mol. Biol. Cell (1992) [Pubmed]
  5. D-aspartate content of erythrocyte membrane proteins is decreased in uremia: implications for the repair of damaged proteins. Perna, A.F., D'Aniello, A., Lowenson, J.D., Clarke, S., De Santo, N.G., Ingrosso, D. J. Am. Soc. Nephrol. (1997) [Pubmed]
  6. Free D-aspartate and D-serine in the mammalian brain and periphery. Hashimoto, A., Oka, T. Prog. Neurobiol. (1997) [Pubmed]
  7. Glutamate receptor, ionotropic, N-methyl D-aspartate 2A (GRIN2A) gene as a positional candidate for attention-deficit/hyperactivity disorder in the 16p13 region. Adams, J., Crosbie, J., Wigg, K., Ickowicz, A., Pathare, T., Roberts, W., Malone, M., Schachar, R., Tannock, R., Kennedy, J.L., Barr, C.L. Mol. Psychiatry (2004) [Pubmed]
  8. Therapeutic efficacy of N-methyl D-aspartate antagonist amantadine in febrile catatonia. Northoff, G., Lins, H., Böker, H., Danos, P., Bogerts, B. Journal of clinical psychopharmacology. (1999) [Pubmed]
  9. beta-Amyloid precursor protein isoforms show correlations with neurones but not with glia of demented subjects. Procter, A.W., Francis, P.T., Holmes, C., Webster, M.T., Qume, M., Stratmann, G.C., Doshi, R., Mann, D.M., Harrison, P.J., Pearson, R.C. Acta Neuropathol. (1994) [Pubmed]
  10. Regional decreases of free D-aspartate levels in Alzheimer's disease. D'Aniello, A., Lee, J.M., Petrucelli, L., Di Fiore, M.M. Neurosci. Lett. (1998) [Pubmed]
  11. Regulation of NMDA receptor phosphorylation by alternative splicing of the C-terminal domain. Tingley, W.G., Roche, K.W., Thompson, A.K., Huganir, R.L. Nature (1993) [Pubmed]
  12. Accumulation of D-aspartic acid with age in the human brain. Man, E.H., Sandhouse, M.E., Burg, J., Fisher, G.H. Science (1983) [Pubmed]
  13. Aspartate: possible neurotransmitter in cerebellar climbing fibers. Wiklund, L., Toggenburger, G., Cuénod, M. Science (1982) [Pubmed]
  14. Marked longevity of human lung parenchymal elastic fibers deduced from prevalence of D-aspartate and nuclear weapons-related radiocarbon. Shapiro, S.D., Endicott, S.K., Province, M.A., Pierce, J.A., Campbell, E.J. J. Clin. Invest. (1991) [Pubmed]
  15. First evidence on induced topological changes in supercoiled DNA by an aluminium D-aspartate complex. Bharathi, n.u.l.l., Jagannatha Rao, K.S., Stein, R. J. Biol. Inorg. Chem. (2003) [Pubmed]
  16. L-Glutamate in the extracellular space regulates endogenous D-aspartate homeostasis in rat pheochromocytoma MPT1 cells. Adachi, M., Koyama, H., Long, Z., Sekine, M., Furuchi, T., Imai, K., Nimura, N., Shimamoto, K., Nakajima, T., Homma, H. Arch. Biochem. Biophys. (2004) [Pubmed]
  17. The stability of a ketamine-morphine solution. Schmid, R., Koren, G., Klein, J., Katz, J. Anesth. Analg. (2002) [Pubmed]
  18. Effect of inhibitors of N-linked oligosaccharide processing on the high-affinity transport of D-aspartate by C6 glioma cells. Deas, J., Silver, I.A., Erecińska, M. Brain Res. (1992) [Pubmed]
  19. Separation of amino acid and peptide stereoisomers by nonionic micelle-mediated capillary electrophoresis after chiral derivatization. Liu, Y.M., Schneider, M., Sticha, C.M., Toyooka, T., Sweedler, J.V. Journal of chromatography. A. (1998) [Pubmed]
  20. Selective association of N-methyl aspartate and quisqualate types of L-glutamate receptor with brain postsynaptic densities. Fagg, G.E., Matus, A. Proc. Natl. Acad. Sci. U.S.A. (1984) [Pubmed]
  21. Macroscopic and microscopic properties of a cloned glutamate transporter/chloride channel. Wadiche, J.I., Kavanaugh, M.P. J. Neurosci. (1998) [Pubmed]
  22. Gene structure of the murine N-methyl D-aspartate receptor subunit NR2C. Suchanek, B., Seeburg, P.H., Sprengel, R. J. Biol. Chem. (1995) [Pubmed]
  23. Multiple subtypes of excitatory amino acid receptors coupled to the hydrolysis of phosphoinositides in rat brain. Littman, L., Glatt, B.S., Robinson, M.B. J. Neurochem. (1993) [Pubmed]
  24. D-aspartate localizations imply neuronal and neuroendocrine roles. Schell, M.J., Cooper, O.B., Snyder, S.H. Proc. Natl. Acad. Sci. U.S.A. (1997) [Pubmed]
  25. Mechanisms of H+ and Na+ changes induced by glutamate, kainate, and D-aspartate in rat hippocampal astrocytes. Rose, C.R., Ransom, B.R. J. Neurosci. (1996) [Pubmed]
  26. Quantification of excitatory amino acid uptake at intact glutamatergic synapses by immunocytochemistry of exogenous D-aspartate. Gundersen, V., Shupliakov, O., Brodin, L., Ottersen, O.P., Storm-Mathisen, J. J. Neurosci. (1995) [Pubmed]
  27. Engineering the substrate specificity of D-amino-acid oxidase. Sacchi, S., Lorenzi, S., Molla, G., Pilone, M.S., Rossetti, C., Pollegioni, L. J. Biol. Chem. (2002) [Pubmed]
  28. Autophosphorylation-dependent targeting of calcium/ calmodulin-dependent protein kinase II by the NR2B subunit of the N-methyl- D-aspartate receptor. Strack, S., Colbran, R.J. J. Biol. Chem. (1998) [Pubmed]
  29. Increased cell proliferation and granule cell number in the dentate gyrus of protein repair-deficient mice. Farrar, C.E., Huang, C.S., Clarke, S.G., Houser, C.R. J. Comp. Neurol. (2005) [Pubmed]
  30. Polymorphic forms of the protein L-isoaspartate (D-aspartate) O-methyltransferase involved in the repair of age-damaged proteins. DeVry, C.G., Clarke, S. J. Hum. Genet. (1999) [Pubmed]
  31. C-terminal tripeptide Ser-Asn-Leu (SNL) of human D-aspartate oxidase is a functional peroxisome-targeting signal. Amery, L., Brees, C., Baes, M., Setoyama, C., Miura, R., Mannaerts, G.P., Van Veldhoven, P.P. Biochem. J. (1998) [Pubmed]
  32. Occurrence of D-aspartic acid and N-methyl-D-aspartic acid in rat neuroendocrine tissues and their role in the modulation of luteinizing hormone and growth hormone release. D'Aniello, A., Di Fiore, M.M., Fisher, G.H., Milone, A., Seleni, A., D'Aniello, S., Perna, A.F., Ingrosso, D. FASEB J. (2000) [Pubmed]
  33. Up-regulation of glutamate receptors is associated with LTP defects in the early stages of diabetes mellitus. Valastro, B., Cossette, J., Lavoie, N., Gagnon, S., Trudeau, F., Massicotte, G. Diabetologia (2002) [Pubmed]
  34. Selfotel in acute ischemic stroke : possible neurotoxic effects of an NMDA antagonist. Davis, S.M., Lees, K.R., Albers, G.W., Diener, H.C., Markabi, S., Karlsson, G., Norris, J. Stroke (2000) [Pubmed]
  35. Decreased uptake and release of D-aspartate in the guinea pig spinal cord after dorsal root section. Potashner, S.J., Tran, P.L. J. Neurochem. (1984) [Pubmed]
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