Stereo‐specific inhibition of acetyl‐ and butyryl‐cholinesterases by enantiomers of cis,cis ‐decahydro‐2‐naphthyl‐N‐ n ‐butylcarbamate

Enantiomers of cis , cis ‐decahydro‐2‐naphthyl‐N‐ n ‐butylcarbamate show stereo‐specific inhibition for acetylcholinesterase and butyrylcholinesterase. For both inhibition reaction, (2 S ,4a R ,8a S )‐ cis , cis ‐decahydro‐2‐naphthyl‐N‐ n ‐ butylcarbamate is more potent than (2 R ,4a S ,8a R )‐ cis , cis ‐decahydro‐2‐naphthyl‐N‐ n ‐butylcarbamate. Optically pure (2 S ,4a R ,8a S )‐(−)‐ and (2 R ,4a S ,8a R )‐(+)‐ 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 (2 S ,4a R ,8a S )‐(−)‐ and (2 R ,4a S ,8a R )‐(+)‐ cis , cis ‐decahydro‐2‐naphthols are determined from the 19 F NMR spectra of their Mosher's ester derivatives. We fail to resolve (2 S ,4a R ,8a R )‐ and (2 R ,4a S ,8a S )‐ trans , cis ‐decahydro‐2‐naphthols from the porcine pancreatic lipase‐catalyzed acetylation of decahydro‐2‐naphthols with vinyl acetate. © 2011 Wiley Periodicals, Inc. J Biochem Mol Toxicol 25:330–339, 2011; View this article online at wileyonlinelibrary.com . DOI 10.1002/jbt.20394