Stereoisomeric lactoyl β methylcholine iodides. Interaction with cholinesterase and acetylcholinesterase

Article abstract of DOI:10.1021/jm00256a006

The preparation and absolute configuration of the stereoisomeric forms of lactoyl β methylcholine iodide with the 2 racemic forms of the molecule are reported. None of the stereoisomers were substrates for the enzyme acetylcholinesterase, whereas two stereoisomers (L lactoyl β methylcholine and D lactoyl L β methylcholine iodide) were poor substrates for cholinesterase. Results are analyzed in the light of previous studies of the chiral requirements of these 2 enzymes and an attempt is made to define the rate limiting or prohibited step in the enzyme catalyzed reaction with these compounds.