N-Methyl-L-aspartate

C5H9I 2-iodo-trans-2-pentene 66688-58-2 410.98 35.096 2 5251 C5H9N04 N-methyl-L-aspartic acid 4226-18-0 504.93 44.358 2... 

The mixture of amino acids released by complete hydrolysis of lipopeptin A was fractionated by ion-exchange chromatography. Each amino acid was isolated and the optical rotation determined. Two moles of L-aspartic acid and 1 mole each of L-glutamic acid, L-serine, l-threonine, N-methyl-L-phenylalanine, L-threo-p-hydroxyglutamic acid and N-methyl-L-aspartic acid were obtained. 

A solution of 88.5 parts of L-phenylalanine methyl ester hydrochloride in 100 parts of water is neutralized by the addition of dilute aqueous potassium bicarbonate, then is extracted with approximately 900 parts of ethyl acetate. The resulting organic solution is washed with water and dried over anhydrous magnesium sulfate. To that solution is then added 200 parts of N-benzyloxycarbonyl-L-aspartic acid-a-p-nitrophenyl, -benzyl diester, and that reaction mixture is kept at room temperature for about 24 hours, then at approximately 65°C for about 24 hours. The reaction mixture is cooled to room temperature, diluted with approximately 390 parts of cyclohexane, then cooled to approximately -18°C in order to complete crystallization. The resulting crystalline product is isolated by filtration and dried to afford -benzyl N-benzyloxycarbonvI-L-aspartyl-L-phenylalanine methyl ester, melting at about 118.5°-119.5°C. 

Cruz SE, Mirshahi T, Thomas B, et al Effects of the abused solvent toluene on recombinant N-methyl-D-aspartate and non-N-methyl-D-aspartate receptors expressed in Xenopus oocytes. J Pharmacol Exp Ther 286 334-340, 1998 De Rosa E, Bartolucci GB, Sigon M, et al Hippuric acid and ortho-cresol as biological indicators ofoccupational exposure to toluene. Am J Ind Med 11 529—537,1987 Delteil P, Stoesser F, Stoesser R L theromanie. Ann Med Psychol (Paris) 1 329-340, 1974... 

Abbreviations N-methyl-D-aspartate (NMDA), alpha-amino-3-hydroxy-5-methyl-4-isoxazole-propionic acid (AMPA), L(+)-2 amino-3-phosphonopropionic acid (L-AP3), 6-cyano-7-nitroqninoxaline (CNQ5Q, 2,3-dihydroxy-6-nitro-7-sulfamyl-benzo-f-quinoxaline (NBQX), 3-(2-carboxypiperazin-4-yl)-propyl-l-phosphonic acid (CPP), 7 Chlorokynnreic... 

N-[N-(benzyloxycarbonyl)-L-aspart-l-oyl-(L-alanyl-L-threonine methyl ester)-4-oyl]-... 

N-[N-(benzyloxycarbonyl)-L-aspart-l-oyl-(L-alanyl-L-threonyl-L-leucyl-L-alanine p-nitrobenzyl ester)-4-oyl]-N-[N-(benzyloxycarbonyl)-L-aspart-l-oyl-(L-alanyl-L-threonyl-L-leucyl-L-alanyl-L-serine p-nitrobenzyl ester)-4-oyl]-N-[N-(benzyloxycarbonyl)-L-aspart-1 -oyl-(glycine ethyl ester)-4-oyl -N-[N-(benzyloxycarbonyl)-L-aspart-l-oyl-(glycyl-L-serine methyl ester)-4-oyl]-... 

Lau, L. F. and Huganir, R. L. Differential tyrosine phosphorylation of N-methyl-D-aspartate receptor subunits. /. Biol. Chem. 270 20036-20041,1995. 

Moon, I. S., Apperson, M. L. and Kennedy, M. B. The major tyrosine-phosphorylated protein in the postsynaptic density fraction is N-methyl-D-aspartate receptor subunit 2B. Proc. Natl Acad. Sci. U.S.A. 91 3954-3958,1994. 

Krystal, J. H., Petrakis, I. L., Mason, G., Trevisan, L. and D Souza, D. C. N-methyl-D-aspartate receptors and alcoholism reward, dependence, treatment, and vulnerability. Pharmacol. Therap. 99 79-94,2003. 

The main building block of PEDC (1 -phenyl-2-[(S)-l-aminoethyl] -N,N -di-ethylcyclopropanecarboxamide), a potent NDMA (N -methyl-D-aspartic acid) receptor antagonist of a cyclopropane structure, N -benzyl-C-cyclopropyl nitrone... 

Harrison, N. L. and Simmonds, M. A. (1985) Quantitative studies on some antagonists of N-methyl-D-aspartate in slices of rat cerebral cortex. Br. J. Pharmacol. 84, 381-391. 

Chen, N., Moshaver, A., and Raymond, L. A. (1997) Differential sensitivity of recombinant N-methyl-D-aspartate receptor subtypes to zinc inhibition. Mol. Pharmacol. 51, 1015-1023. 

Stump, G.L., Lynch, J.J., Macaulay, A., Wafford, K.A., Koblan, K.S. and Liverton, N.J. (2004) NR2B-selective N-methyl-D-aspartate antagonists synthesis and evaluation of 5-substituted benzimidazoles. Journal of Medicinal Chemistry, 47, 2089-2096. 

Patel MN, Yim GK, Isom GE. 1993. N-methyl-D-aspartate receptors mediate cyanide-induced cytotoxicity in hippocampal cultures. Neurotoxicology 14(l) 35-40. 

Cambonie G, Laplanche L, Kamenka JM, Barbanel G. 2000. N-Methyl-D-aspartate but not glutamate induces the release of hydroxyl radicals in the neonatal rat modulation by group I metabotropic glutamate receptors. J Neurosci Res... 

Arendtnielsen L, Petersenfelix S, Fischer M, et al (1995) The effect of N-methyl-o-aspartate antagonist (ketamine) on single and repeated nociceptive stimuli a placebo-controlled experimental human study. Anesth Analg 81 63-68 Areosa SA, Sherriff F (2003) Memantine for dementia (Cochrane Review). Cochrane Database Syst Rev 1 CD003154... 

Fan GH, Zhao J, Wu YL, Lou LG, ZhangZ, Jing Q, Ma L, Pei G (1998) N-Methyl-D-aspartate attenuates opioid receptor-mediated G protein activation and this process involves protein kinase C. Mol Pharmacol 53 684-690... 

Alternatively, oxazolones have been used as reagents to activate and to couple N-protected dicarboxylic amino acids wherein the carboxylate moiety acts as the nucleophile. For example, 2,4-dimethyl-5(4//)-oxazolone 255 reacts with N-benzyloxycarbonyl-L-aspartic acid to give a mixture of the anhydrides 256 and 257. Subsequent reaction of 256 and 257 with phenylalanine methyl ester hydrochloride and A-methylmorpholine produces a mixture of the a-isomer 258 and p-isomer 259 of Al-benzyloxycarbonyl-aspartylphenylalanine methyl ester (Scheme 7.83). °... 

Yun. H.Y., Gonzalez-Zulueta, M., Dawson, V.L. and Dawson, T.M. Nitric oxide mediates N-methyl-D-aspartate receptor-induced activation of p21ras (1998) Proc Natl Acad Sd U S A 95,... 

Fischer BD, Carrigan KA, Dykstra LA Effects of N-methyl-D-aspartate receptor antagonists on acute morphine-induced and L-methadone-induced antinociception in mice. 3 Pain 2005 6 425. [PMID 15993820]... 

N 017 "Conformational Analysis of Macromolecules. IV. Helical Structures of PolyfL-alanine), Poly(L-valine), Poly(p-methyl-L-aspartate), Polyly-methyl-l.-glutamate),... 

The amino acid L-glutamate is the main excitatory neurotransmitter of the central nervous system (Fonnum, 1984). Glutamate exerts its excitatory effects either by activation of several G-protein-coupled metabotropic glutamate receptors or by induction of ion fluxes by different classes of ionotropic receptors. The NMDA receptor is one of those glutamate-gated ion channels which got its name from its selective artificial agonist NMDA (N-methyl-D-aspartate) and which controls slow but persistent ion fluxes of Na+, K+, and Ca2+ across the cell membrane. 

Allen, R. M. and Dykstra, L. A. N-Methyl-D-aspartate receptor antagonists potentiate the antinociceptive effects of morphine in squirrel monkeys, J. Pharmacol. Exp. Ther. 2001, 298, 288-297. 

Coughenour L. L. and Barr, B. M. Use of trifluoroperazine isolates pHJifenprodil binding site in rat brain membranes with the pharmacology of the voltage-independent ifenprodil site on N-methyl-D-aspartate receptors containing NR2B subunits, J. Pharmacol. Exp. Ther. 2001, 296, 150-159. 

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