Synthesis and pharmacological characterization at glutamate receptors of the four enantiopure isomers of tricholomic acid
Research output: Contribution to journal › Journal article › Research › peer-review
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.
|Journal||Journal of Medicinal Chemistry|
|Publication status||Published - 2008|
- Amino Acids, Animals, CHO Cells, Cell Line, Cloning, Molecular, Cricetinae, Cricetulus, Cyclization, Glycine, Humans, Isoxazoles, Molecular Structure, Rats, Receptors, Glutamate, Stereoisomerism, Structure-Activity Relationship