title: Stereo-specific inhibition of acetyl- and butyryl-cholinesterases by enantiomers of cis,cis-decahydro-2-naphthyl-N-n-butylcarbamate.
abstract: Enantiomers of cis,cis-decahydro-2-naphthyl-N-n-butylcarbamate show stereo-specific inhibition for acetylcholinesterase and butyrylcholinesterase. For both inhibition reaction, (2S,4aR,8aS)-cis,cis-decahydro-2-naphthyl-N-n- butylcarbamate is more potent than (2R,4aS,8aR)-cis,cis-decahydro-2-naphthyl-N-n-butylcarbamate. Optically pure (2S,4aR,8aS)-(-)- and (2R,4aS,8aR)-(+)-cis,cis-decahydro-2-naphthols are resolved by the porcine pancreatic lipase-catalyzed acetylation of decahydro-2-naphthols with vinyl acetate. Absolute configurations and the enantiomeric excess values of (2S,4aR,8aS)-(-)- and (2R,4aS,8aR)-(+)-cis,cis-decahydro-2-naphthols are determined from the (19)F NMR spectra of their Mosher's ester derivatives. We fail to resolve (2S,4aR,8aR)- and (2R,4aS,8aS)-trans,cis-decahydro-2-naphthols from the porcine pancreatic lipase-catalyzed acetylation of decahydro-2-naphthols with vinyl acetate.
authors.affiliation: Department of Internal Medicine, Chung Shan Medical University Hospital and School of Medicine, Chung Shan Medical University, Taichung 402, Taiwan.
authors.forename: Ming-Cheng
authors.initials: MC
authors.lastname: Lin
authors.forename: Shyh-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: D000107:Acetylation; D000110:Acetylcholinesterase / Q000737:chemistry / Q000378:metabolism*; D000818:Animals; D055162:Biocatalysis / Q000187:drug effects; D002091:Butyrylcholinesterase / Q000737:chemistry / Q000378:metabolism*; D002219:Carbamates / Q000737:chemistry / Q000494:pharmacology*; D002236:Carbohydrate Conformation / Q000187:drug effects; D002800:Cholinesterase Inhibitors / Q000737:chemistry / Q000494:pharmacology*; D004952:Esters / Q000737:chemistry; D007700:Kinetics; D008049:Lipase / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D009284:Naphthols / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity; D013552:Swine; D014753:Vinyl Compounds / Q000737:chemistry
chemical_list: D002219:Carbamates; D002800:Cholinesterase Inhibitors; D004952:Esters; D009284:Naphthols; D014753:Vinyl Compounds; D008049:Lipase; D000110:Acetylcholinesterase; D002091:Butyrylcholinesterase; C011566:vinyl acetate