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|標題:||Stereo-Specific Inhibition of Acetyl- and Butyryl-Cholinesterases by Enantiomers of Cis,Cis-Decahydro-2-naphthyl-N-n-butylcarbamate||作者:||Lin, M.C.
|關鍵字:||Acetylcholinesterase;Butyrylcholinesterase;Carbamate Inhibitor;Stereospecificity;structure-reactivity relationships;pancreatic cholesterol esterase;stereoselective inhibition;molecular recognition;acetylcholinesterase;butyrylcholinesterase;mechanism;site;hydrolysis;substrate||Project:||Journal of Biochemical and Molecular Toxicology||期刊/報告no：:||Journal of Biochemical and Molecular Toxicology, Volume 25, Issue 5, Page(s) 330-339.||摘要:||
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. (C) 2011 Wiley Periodicals, Inc. J Biochem Mol Toxicol 25:330-339, 2011; View this article online at wileyonlinelibrary. com. DOI 10:1002/jbt.20394
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