Home Other Building Blocks L-Glutamic acid, N-acetyl-L-α-aspartyl-

L-Glutamic acid, N-acetyl-L-α-aspartyl-

CAS No.:
3106-85-2
Catalog Number:
AG00321K
Molecular Formula:
C11H16N2O8
Molecular Weight:
304.2533
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Purity
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Product Description
Catalog Number:
AG00321K
Chemical Name:
L-Glutamic acid, N-acetyl-L-α-aspartyl-
CAS Number:
3106-85-2
Molecular Formula:
C11H16N2O8
Molecular Weight:
304.2533
MDL Number:
MFCD00076652
IUPAC Name:
(2S)-2-[[(2S)-2-acetamido-3-carboxypropanoyl]amino]pentanedioic acid
InChI:
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
InChI Key:
OPVPGKGADVGKTG-BQBZGAKWSA-N
SMILES:
OC(=O)CC[C@@H](C(=O)O)NC(=O)[C@@H](NC(=O)C)CC(=O)O
UNII:
1W8M12WXYL
NSC Number:
758468
Properties
Complexity:
448  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Defined Bond Stereocenter Count:
0
Exact Mass:
304.091g/mol
Formal Charge:
0
Heavy Atom Count:
21  
Hydrogen Bond Acceptor Count:
8  
Hydrogen Bond Donor Count:
5  
Isotope Atom Count:
0
Molecular Weight:
304.255g/mol
Monoisotopic Mass:
304.091g/mol
Rotatable Bond Count:
9  
Topological Polar Surface Area:
170A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-2.1  
Literature
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Synthesis of N-acetylaspartyl-glutamate (NAAG) and N-acetylaspartate (NAA) in axons and glia of the crayfish medial giant nerve fiber. Advances in experimental medicine and biology 20060101
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Neuroprotective effect of N-acetyl-aspartyl-glutamate in combination with mild hypothermia in the endothelin-1 rat model of focal cerebral ischaemia. Journal of neurochemistry 20051201
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Central N-acetyl aspartylglutamate deficit: a possible pathogenesis of schizophrenia. Medical science monitor : international medical journal of experimental and clinical research 20050901
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Effect of N-acetylaspartylglutamate (NAAG) on non-quantal and spontaneous quantal release of acetylcholine at the neuromuscular synapse of rat. Journal of neurochemistry 20050701
Regulation of glutamate carboxypeptidase II hydrolysis of N-acetylaspartylglutamate (NAAG) in crayfish nervous tissue is mediated by glial glutamate and acetylcholine receptors. Journal of neurochemistry 20050501
Metabolic characterization of distinct neuroanatomical regions in rats by magic angle spinning 1H nuclear magnetic resonance spectroscopy. Magnetic resonance in medicine 20050501
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Chronic phencyclidine administration induces schizophrenia-like changes in N-acetylaspartate and N-acetylaspartylglutamate in rat brain. Schizophrenia research 20050301
In vitro 1H NMR spectroscopy shows an increase in N-acetylaspartylglutamate and glutamine content in the hippocampus of amygdaloid-kindled rats. Journal of neurochemistry 20050301
NAAG reduces NMDA receptor current in CA1 hippocampal pyramidal neurons of acute slices and dissociated neurons. Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20050101
Group II mGluR-induced long term depression in the dentate gyrus in vivo is NMDA receptor-independent and does not require protein synthesis. Neuropharmacology 20050101
High-field localized 1H NMR spectroscopy in the anesthetized and in the awake monkey. Magnetic resonance imaging 20041201
In vivo quantitative 1H MRS of cerebellum and evaluation of quantitation reproducibility by simulation of different levels of noise and spectral resolution. Magnetic resonance imaging 20041201
Serotonin1B receptors: from protein to physiological function and behavior. Neuroscience and biobehavioral reviews 20041001
Quantitative 1H-MRS of healthy human cortex, hippocampus, and thalamus: metabolite concentrations, quantification precision, and reproducibility. Journal of magnetic resonance imaging : JMRI 20040901
Clinical correlation of brain MRI and MRS abnormalities in patients with Wilson disease. Neurology 20040824
Aspartoacylase deficiency does not affect N-acetylaspartylglutamate level or glutamate carboxypeptidase II activity in the knockout mouse brain. Brain research 20040806
Biosynthesis of NAAG by an enzyme-mediated process in rat central nervous system neurons and glia. Journal of neurochemistry 20040801
Antinociceptive effects of N-acetylaspartylglutamate (NAAG) peptidase inhibitors ZJ-11, ZJ-17 and ZJ-43 in the rat formalin test and in the rat neuropathic pain model. The European journal of neuroscience 20040701
Identification of the N-glycosylation sites on glutamate carboxypeptidase II necessary for proteolytic activity. Protein science : a publication of the Protein Society 20040601
SH-SY5Y neuroblastoma cells: a model system for studying biosynthesis of NAAG. Neuroreport 20040519
Severe hypomyelination associated with increased levels of N-acetylaspartylglutamate in CSF. Neurology 20040511
The cloning and characterization of a second brain enzyme with NAAG peptidase activity. Journal of neurochemistry 20040501
A comparative study of myo-inositol quantification using LCmodel at 1.5 T and 3.0 T with 3 D 1H proton spectroscopic imaging of the human brain. Magnetic resonance imaging 20040501
NAAG peptidase inhibition reduces locomotor activity and some stereotypes in the PCP model of schizophrenia via group II mGluR. Journal of neurochemistry 20040501
Protection against glucose-induced neuronal death by NAAG and GCP II inhibition is regulated by mGluR3. Journal of neurochemistry 20040401
Synthesis of urea-based inhibitors as active site probes of glutamate carboxypeptidase II: efficacy as analgesic agents. Journal of medicinal chemistry 20040325
NAAG fails to antagonize synaptic and extrasynaptic NMDA receptors in cerebellar granule neurons. Neuropharmacology 20040301
Measurement of brain glutamate using TE-averaged PRESS at 3T. Magnetic resonance in medicine 20040301
Tumor target prostate specific membrane antigen (PSMA) and its regulation in prostate cancer. Journal of cellular biochemistry 20040215
Reduced isolation-induced aggressiveness in mice following NAALADase inhibition. Psychopharmacology 20040201
GCP II (NAALADase) inhibition suppresses mossy fiber-CA3 synaptic neurotransmission by a presynaptic mechanism. Journal of neurophysiology 20040101
Glutamate carboxypeptidase II gene expression in the human frontal and temporal lobe in schizophrenia. Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20040101
Early embryonic death of glutamate carboxypeptidase II (NAALADase) homozygous mutants. Synapse (New York, N.Y.) 20031215
N-acetylaspartylglutamate and beta-NAAG protect against injury induced by NMDA and hypoxia in primary spinal cord cultures. Brain research 20031121
Magnetization transfer imaging and magnetic resonance spectroscopy of normal-appearing white matter in late-life major depression. Journal of magnetic resonance imaging : JMRI 20031101
Metabotropic glutamate receptor regulation of neuronal cell death. Experimental neurology 20031101
High-field proton MRS of human brain. European journal of radiology 20031101
Proton MRS reveals frontal lobe metabolite abnormalities in idiopathic generalized epilepsy. Neurology 20031014
Effect of carbohydrate moieties on the folate hydrolysis activity of the prostate specific membrane antigen. The Prostate 20031001
Effects of GCP-II inhibition on responses of dorsal horn neurones after inflammation and neuropathy: an electrophysiological study in the rat. Neuropeptides 20031001
Expression of glutamate transporter, GABRA6, serine proteinase inhibitor 2 and low levels of glutamate and GABA in the brain of knock-out mouse for Canavan disease. Brain research bulletin 20030830
Brain metabolism in Alzheimer disease and vascular dementia assessed by in vivo proton magnetic resonance spectroscopy. Psychiatry research 20030730
Prostate targeting ligands based on N-acetylated alpha-linked acidic dipeptidase. Biochemical and biophysical research communications 20030718
Regulation of glutamate carboxypeptidase II function in corticolimbic regions of rat brain by phencyclidine, haloperidol, and clozapine. Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20030701
N-acetylaspartate and N-Acetylaspartylglutamate deficits in superior temporal cortex in schizophrenia and bipolar disorder: a postmortem study. Biological psychiatry 20030615
Reductions in N-acetylaspartylglutamate and the 67 kDa form of glutamic acid decarboxylase immunoreactivities in the visual system of albino and pigmented rats after optic nerve transections. The Journal of comparative neurology 20030407
[In vitro effects of antiallergic eyedrops on complement activation induced by particulate matter]. Journal francais d'ophtalmologie 20030401
Proton MRS profile of cerebral metabolic abnormalities in Krabbe disease. Neurology 20030311
Characterisation of the 1H and 13C NMR spectra of N-acetylaspartylglutamate and its detection in urine from patients with Canavan disease. Journal of pharmaceutical and biomedical analysis 20030310
Modulation of epileptiform burst frequency by the metabotropic glutamate receptor subtype mGluR3. Epilepsy research 20030301
Characterization of oligodendrogliomas using short echo time 1H MR spectroscopic imaging. NMR in biomedicine 20030201
Cerebral proton magnetic resonance spectroscopy of a patient with giant axonal neuropathy. Brain & development 20030101
Morphology and ultrastructure of rat hippocampal formation after i.c.v. administration of N-acetyl-L-aspartyl-L-glutamate. Neuroscience 20030101
Group II and III metabotropic glutamate receptors and the control of the nucleus reticularis thalami input to rat thalamocortical neurones in vitro. Neuroscience 20030101
Brain metabolite composition during early human brain development as measured by quantitative in vivo 1H magnetic resonance spectroscopy. Magnetic resonance in medicine 20021201
[N acetyl-aspartyl glutamic acid (NAAGA) inhibits the adhesion of leukocytes to activated endothelial cells and down-modulates the cytokine-induced expression of adhesion molecules]. Journal francais d'ophtalmologie 20021201
Kinetics and inhibition of glutamate carboxypeptidase II using a microplate assay. Analytical biochemistry 20021101
High-performance liquid chromatography method for detecting prostate-specific membrane antigen activity. Analytical biochemistry 20021101
Brain metabolite changes in cortical grey and normal-appearing white matter in clinically early relapsing-remitting multiple sclerosis. Brain : a journal of neurology 20021001
Maturation of the human fetal brain as observed by 1H MR spectroscopy. Magnetic resonance in medicine 20021001
Deletion of the glutamate carboxypeptidase II gene in mice reveals a second enzyme activity that hydrolyzes N-acetylaspartylglutamate. Journal of neurochemistry 20021001
Glutamine uptake and metabolism to N-acetylaspartylglutamate (NAAG) by crayfish axons and glia. Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology 20021001
Molecular modeling of the interactions of glutamate carboxypeptidase II with its potent NAAG-based inhibitors. Journal of medicinal chemistry 20020912
A short-echo-time proton magnetic resonance spectroscopic imaging study of temporal lobe epilepsy. Epilepsia 20020901
NAALADase (GCP II) inhibition prevents cocaine-kindled seizures. Neuropharmacology 20020901
Mechanism of NMDA receptor contribution to axon-to-glia signaling in the crayfish medial giant nerve fiber. Glia 20020401
Neuroprotective effects of N-acetylaspartylglutamate in a neonatal rat model of hypoxia-ischemia. European journal of pharmacology 20020222
Effect of 2-(phosphono-methyl)-pentanedioic acid on allodynia and afferent ectopic discharges in a rat model of neuropathic pain. The Journal of pharmacology and experimental therapeutics 20020201
Reproducibility of in vivo metabolite quantification with proton magnetic resonance spectroscopic imaging. Journal of magnetic resonance imaging : JMRI 20020201
Measurement of glutamate carboxypeptidase II (NAALADase) enzyme activity by the hydrolysis of [³H]-N-acetylaspartylglutamate (NAAG). Current protocols in pharmacology 20020201
N-Acetyl-L-aspartyl-L-glutamate changes functional and structural properties of rat blood-brain barrier. Neuroscience letters 20020111
Group II metabotropic glutamate receptors modulate extracellular glutamate in the nucleus accumbens. The Journal of pharmacology and experimental therapeutics 20020101
N-acetylaspartate is an axon-specific marker of mature white matter in vivo: a biochemical and immunohistochemical study on the rat optic nerve. Annals of neurology 20020101
Differential expression of carnosine, homocarnosine and N-acetyl-L-histidine hydrolytic activities in cultured rat macroglial cells. Journal of molecular neuroscience : MN 20011201
Neuroprotection mediated by glutamate carboxypeptidase II (NAALADase) inhibition requires TGF-beta. European journal of pharmacology 20011026
Neuroprotection afforded by NAAG and NAALADase inhibition requires glial cells and metabotropic glutamate receptor activation. European journal of pharmacology 20010824
Spinal N-acetyl-alpha-linked acidic dipeptidase (NAALADase) inhibition attenuates mechanical allodynia induced by paw carrageenan injection in the rat. Brain research 20010803
In vivo short echo time 1H-magnetic resonance spectroscopic imaging (MRSI) of the temporal lobes. NeuroImage 20010801
Design of NAALADase inhibitors: a novel neuroprotective strategy. Current medicinal chemistry 20010701
Group II mGlu receptor agonists fail to protect against various neurotoxic insults induced in murine cortical, striatal and cerebellar granular pure neuronal cultures. Neuropharmacology 20010701
Postmortem degradation of N-acetyl aspartate and N-acetyl aspartylglutamate: an HPLC analysis of different rat CNS regions. Neurochemical research 20010601
Absence of N-acetylaspartate in the human brain: impact on neurospectroscopy? Annals of neurology 20010401
[Synthesis and release of N-acetylaspartyl glutamate (NAAG) in medial giant axons in crayfish]. Rossiiskii fiziologicheskii zhurnal imeni I.M. Sechenova 20010401
beta-NAAG rescues LTP from blockade by NAAG in rat dentate gyrus via the type 3 metabotropic glutamate receptor. Journal of neurophysiology 20010301
Quantitative short echo time proton magnetic resonance spectroscopic imaging study of malformations of cortical development causing epilepsy. Brain : a journal of neurology 20010201
[Antioxidant effects of mast cell inhibitors in a human conjunctival cell line]. Journal francais d'ophtalmologie 20010201
Amino acids are still as exciting as ever. Current opinion in pharmacology 20010201
Regional distribution and pharmacological characteristics of [3H]N-acetyl-aspartyl-glutamate (NAAG) binding sites in rat brain. Neurochemistry international 20010101
Inhibition of spinal N-acetylated-alpha-linked acidic dipeptidase produces an antinociceptive effect in the rat formalin test. Neuroscience 20010101
NAAG inhibits KCl-induced [(3)H]-GABA release via mGluR3, cAMP, PKA and L-type calcium conductance. The European journal of neuroscience 20010101
N-acetylaspartylglutamate (NAAG) is the probable mediator of axon-to-glia signaling in the crayfish medial giant nerve fiber. Neuroscience 20010101
Synthesis and release of N-acetylaspartylglutamate (NAAG) by crayfish nerve fibers: implications for axon-glia signaling. Neuroscience 20010101
Mechanisms for clearance of released N-acetylaspartylglutamate in crayfish nerve fibers: implications for axon-glia signaling. Neuroscience 20010101
Characterization of [(3)H]-LY354740 binding to rat mGlu2 and mGlu3 receptors expressed in CHO cells using semliki forest virus vectors. Neuropharmacology 20000724
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