title: Glutamic acid agonists. Stereochemical and conformational studies of DL-alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) and related compounds.
abstract: Microelectrophoretic techniques were used to study the effects of the optical isomers of the L-glutamic acid (GLUT) agonist AMPA on cat spinal neurones. Both enantiomers excited spinal interneurones, L-AMPA being more potent than D-AMPA, and, like GLUT, this excitation was blocked by L-glutamic acid diethyl ester but not by 2-amino-5-phosphonovaleric acid. ATPA and ABPA, in which the methyl group of AMPA was replaced by more bulky substituents, were also GLUT agonists, although weaker than AMPA. O-methyl-AMPA was inactive, suggesting that a necessary condition for GLUT agonist or antagonist actions of this class of compound is the presence of an acidic group in the position equivalent with the omega-position of GLUT.
mesh_terms: D015763:2-Amino-5-phosphonovalerate; D000818:Animals; D002415:Cats; D005071:Evoked Potentials / Q000187:drug effects; D005727:Ganglia, Spinal / Q000187:drug effects; D005971:Glutamates / Q000494:pharmacology*; D018698:Glutamic Acid; D007051:Ibotenic Acid / Q000031:analogs & derivatives / Q000494:pharmacology*; D007395:Interneurons / Q000187:drug effects; D010080:Oxazoles / Q000494:pharmacology*; D013116:Spinal Cord / Q000187:drug effects*; D013237:Stereoisomerism; D009435:Synaptic Transmission / Q000187:drug effects; D014633:Valine / Q000031:analogs & derivatives / Q000494:pharmacology; D018350:alpha-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid
chemical_list: D005971:Glutamates; D010080:Oxazoles; C011829:glutamic acid diethyl ester; D007051:Ibotenic Acid; D018698:Glutamic Acid; D015763:2-Amino-5-phosphonovalerate; D018350:alpha-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid; D014633:Valine