Esters of choline and β-trimethylammoniopropionic acid: geometrical isomerism and anti-acetylcholinesterase activity
- 1 March 1969
- journal article
- Published by Oxford University Press (OUP) in Journal of Pharmacy and Pharmacology
- Vol. 21 (3) , 145-154
- https://doi.org/10.1111/j.2042-7158.1969.tb08219.x
Abstract
The preparation of the choline esters of cis- and trans-4-t-butylcyclohexanecarboxylic acid is reported. The similar inhibitory potency displayed by these isomers towards the acetylcholinesterase catalysed hydrolysis of acetylcholine is explained on the basis of the binding of a thermodynamically unstable conformation of the cis-isomer to the active site. Similar studies employing the β-trimethylammoniopropionate esters of cis- and trans-4-t-butylcyclohexanol suggest that the “reverse esters” do not bind to the active site in an identical manner to the acylcholines.Keywords
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