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標題: Synthesis of Enantiomers of exo-2-Norbornyl-N-n-butylcarbamate and endo-2-Norbornyl-N-n-butylcarbamate for Stereoselective Inhibition of Acetylcholinesterase
作者: Chiou, S.Y.
Huang, C.F.
Yeh, S.J.
Chen, I.R.
Lin, G.L.
關鍵字: acetylcholinesterase;carbamate inhibitor;enantiomer;stereoselectivity;resolution by lipase;structure-reactivity relationships;pre-steady-state;cholesterol;esterase;alzheimers-disease;molecular recognition;butyrylcholinesterase;mechanism;lipase;site;cholinesterases
Project: Chirality
期刊/報告no:: Chirality, Volume 22, Issue 2, Page(s) 267-274.
The acetylcholinesterase inhibition by enantiomers of exo- and endo-2norbornyl-N-n-butylcarbamates shows high stereoselelectivity. For the acetylcholinesterase inhibitions by (R)-(+)- and (S)-(-)-exo-2-norbornyl-N-n-butylcarbamates, the R-enantiomer is more potent than the S-enantiomer. But, for the acetylcholinesterase inhibitions by (R)-(+)- and (S)-(-)-endo-2-norbornyl-N-n-butylcarbamates, the S-enantiomer is more potent than the R-enantiomer. Optically Pure (R)-(+)-exo-, (S)-(-)-exo-, (R)-H-endo-, and (S)-(-)-endo-2-norbornyl-N-n-butylcarbamates are synthesized from condensations of optically pure (R)-(+)-exo-, (S)-(-)-exo-, (R)-(+)-endo-, and (S)-(-)-endo-2-norborneols with n-butyl isocyanate, respectively. Optically pure norborneols are obtained from kinetic resolutions of their racemic esters by lipase catalysis in organic solvent. Chirality 22:267-274, 2010. (C) 2009 Wiley-liss, Inc.
ISSN: 0899-0042
DOI: 10.1002/chir.20739
Appears in Collections:化學系所

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