A NEW SYNTHESIS, RESOLUTION AND IN VITRO ACTIVITIES OF (R)- AND (S)-β-PHENYL-GABA

Article abstract of DOI:10.1016/S0040-4020(01)82032-9

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.