A new synthesis resolution and in vitro activities of (R)- and (S)-β-Phenyl-Gaba

Abstract β-Phenyl- GABA ( 2 ) was resolved by separation by crystallization and/or h.p.l.c. of the diastereoisomeric (R)-(-)-pantolactone esters of the N-phthalimido protected β-phenyl- GABA . The absolute stereochemical assignments obtained from chiroptical studies of the enantiomers (8a) and (8b) and an X-ray crystallographic study of the diastereoisomer (7a) were supported by the activities of the enantiomers (8a) and (8b) in binding and electrophysiological studies. Details of synthesis, binding, electrophysiological, chiroptical and X-ray crystallographic studies are reported.