Stereo-specific inhibition of acetyl- and butyryl-cholinesterases by enantiomers of cis,cis-decahydro-2-naphthyl-N-n-butylcarbamate
✍ Scribed by Ming-Cheng Lin; Shyh-Jei Yeh; I-Ru Chen; Gialih Lin
- Book ID
- 102298614
- Publisher
- John Wiley and Sons
- Year
- 2011
- Tongue
- English
- Weight
- 149 KB
- Volume
- 25
- Category
- Article
- ISSN
- 1095-6670
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✦ Synopsis
Abstract
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