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J Med Chem. 2008 Apr 10;51(7):2311-5. doi: 10.1021/jm701394a. Epub 2008 Mar 14.

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

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Istituto di Chimica Farmaceutica e Tossicologica P. Pratesi, Università degli Studi di Milano, Via Mangiagalli 25, Milan, Italy.


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.

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