Synthesis and biology of the rigidified glutamate analogue, trans-2-carboxyazetidine-3-acetic acid (t-CAA)

Abstract

Chemical approaches to the (−)- and (+)-trans-2-carboxyazetidine-3-acetic acids (−)-1 and (+)-1, and their homologues (−)-2 and (+)-2, compounds that represent rigidified analogues of glutamate (glu), are reported together with the complete biological characterization of (+)-1 (t-CAA) at the known glu recognition sites. t-CAA was found to be an inhibitor of Na+-dependent glu uptake and to act as a kainate receptor ligand.