title: Stereoselective inhibition of butyrylcholinesterase by enantiomers of exo- and endo-2-norbornyl-N-n-butylcarbamates.
abstract: Enantiomers of exo- and endo-2-norbornyl-N-n-butylcarbamates were characterized as pseudo substrate inhibitors of butyrylcholinesterase. These inhibitions discriminate enantiomers of the inhibitors and therefore show stereoselectivity for the enzyme. For inhibitions by (R)-(+)- and (S)-(-)-exo-2-norbornyl-N-n-butylcarbamates, R-enantiomer is a more potent inhibitor than S-enantiomer. But, for inhibitions by (R)-(+)- and (S)-(-)-endo-2-norbornyl-N-n-butylcarbamates, S-enantiomer is a more potent inhibitor than R-enantiomer. Optically pure (R)-(+)-exo-, (S)-(-)-exo-, (R)-(+)-endo-, and (S)-(-)-endo-2-norbornyl-N-n-butylcarbamates were synthesized from condensations of optically pure (R)-(+)-exo-, (S)-(-)-exo-, (R)-(+)-endo-, and (S)-(-)-endo-2-norborneols with n-butyl isocyanate, respectively. Optically pure norborneols were obtained from kinetic resolution of their racemic esters by lipase catalysis in organic solvent.
authors.affiliation: Division of Neurosurgery, Chung Shan Medical University Hospital, Taichung, Taiwan.
authors.forename: Shyh-Ying
authors.initials: SY
authors.lastname: Chiou
authors.forename: Chun-Fu
authors.initials: CF
authors.lastname: Huang
authors.forename: Shih-Jei
authors.initials: SJ
authors.lastname: Yeh
authors.forename: I-Ru
authors.initials: IR
authors.lastname: Chen
authors.forename: Gialih
authors.initials: G
authors.lastname: Lin
mesh_terms: D002091:Butyrylcholinesterase / Q000187:drug effects*; D002219:Carbamates / Q000494:pharmacology*; D002800:Cholinesterase Inhibitors / Q000494:pharmacology*; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism
chemical_list: D002219:Carbamates; D002800:Cholinesterase Inhibitors; D002091:Butyrylcholinesterase