Synthesis and pharmacological characterization at glutamate receptors of the four enantiopure isomers of tricholomic acid

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The two enantiomeric pairs of erythro- and threo-amino-(3'-hydroxy-4',5'-dihydro-isoxazol-5'-yl)-acetic acids were synthesized via the 1,3-dipolar cycloaddition of bromonitrile oxide to ( R)- or ( S)-3-( tert-butoxycarbonyl)-2,2-dimethyl-4-vinyloxazolidine. The pharmacological profiles of the studied amino acids reflect the relationship between the activity/selectivity and the stereochemistry of the two stereogenic centers: while the (2 S,5' S) stereoisomer is an agonist at the AMPA and KA receptors, its (2 R,5' R) enantiomer interacts selectively with the NMDA receptors; the (2 S,5' R) stereoisomer is the only one capable to activate the mGluRs.
Original languageEnglish
JournalJournal of Medicinal Chemistry
Issue number7
Pages (from-to)2311-2315
Publication statusPublished - 2008

    Research areas

  • Amino Acids, Animals, CHO Cells, Cell Line, Cloning, Molecular, Cricetinae, Cricetulus, Cyclization, Glycine, Humans, Isoxazoles, Molecular Structure, Rats, Receptors, Glutamate, Stereoisomerism, Structure-Activity Relationship

ID: 3800724