Enzymatic resolution and cholinergic properties of (±)3-quinuclidinol derivatives

Moshe Rehavi*, Saul Maayani, Mordechai Sokolovsky

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Resolution of (±)3-quinuclidinol into its enantiomers was obtained, at relatively high yield, based on the stereoselective enzymatic hydrolysis of R-(-)-3-quinuclidinyl butyrate by horse serum butyrylcholinesterase. The S-(+) isomer of 3-quinuclidinol was obtained from the racemate of 3-quinuclidinyl butyrate by a complete digestion of the (-) ester; the R-(-) isomer of 3-quinuclidinol was prepared by a partial hydrolysis of the racemate. The enantiomers obtained by this method were of high optical purity ([α]D25 = (+)46°). The cholinergic interactions of the benzilate esters of the 3-quinuclidinol enantiomers were characterized in mice in vivo and in isolated guinea pig ileum. The R to S potency ratio is around 10-15 for the muscarinic antagonist 3-quinuclidinyl benzilate (QNB) in the in vivo experiments compared to the reported ratio of 100 in competition experiments in vitro.

Original languageEnglish
Pages (from-to)1293-1302
Number of pages10
JournalLife Sciences
Volume21
Issue number9
DOIs
StatePublished - 1 Nov 1977

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