title: Stereoselective inhibition of cholesterol esterase by enantiomers of exo- and endo-2-norbornyl-N-n-butylcarbamates.
abstract: Four stereoisomers of 2-norbornyl-N-n-butylcarbamates are characterized as the pseudo substrate inhibitors of cholesterol esterase. Cholesterol esterase shows enantioselective inhibition for enantiomers of exo- and endo-2-norbornyl-N-n-butylcarbamates. For the inhibitions by (R)-(+)- and (S)-(-)-exo-2-norbornyl-N-n-butylcarbamates, the R-enantiomer is 6.8 times more potent than the S-enantiomer. For the inhibitions by (R)-(+)- and (S)-(-)-endo-2-norbornyl-N-n-butyl-carbamates, the S-enantiomer is 4.6 times more potent than the R-enantiomer. The enzyme-inhibitor complex models have been proposed to explain these different enantioselectivities.
authors: Department of Internal Medicine, Chung Shan Medical University Hospital, School of Medicine, Chung-Shan Medical University, Taichung 402, Taiwan.
authors: Ming-Cheng
authors: MC
authors: Lin
authors: Shyh-Jei
authors: SJ
authors: Yeh
authors: I-Ru
authors: IR
authors: Chen
authors: Gialih
authors: G
authors: Lin
mesh_terms: D000818:Animals; D002219:Carbamates / Q000737:chemistry* / Q000494:pharmacology*; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000494:pharmacology*; D007700:Kinetics; D009636:Norbornanes / Q000737:chemistry* / Q000494:pharmacology*; D013237:Stereoisomerism; D002787:Sterol Esterase / Q000037:antagonists & inhibitors / Q000737:chemistry*; D013552:Swine
chemical_list: C549224:2-norbornyl-N-n-butylcarbamate; D002219:Carbamates; D004791:Enzyme Inhibitors; D009636:Norbornanes; D002787:Sterol Esterase