Acetylcholinesterase Substrates: Acetoxymethylpyridines and Benzyl Acetate

Add time:07/17/2019    Source:sciencedirect.com

2-Acetoxymethylpyridine (I) and 2-, 3-, and 4-acetoxymethylpyridinium methiodides (II, III, and IV, respectively) are spectrophotometrically useful substrates for acetylcholinesterase. Compounds III and IV are highly water soluble yet equal to phenyl acetate in resistance toward aqueous hydrolysis. Compound I and benzyl acetate are appreciably more stable. Kinetic constants for both enzymatic and nonenzymatic hydrolysis are reported. Comparison of the relative rates of acylation of acetylcholinesterase by Compounds I, III, and IV and phenyl acetate indicates considerable kinetic selectivity. Contrary to general expectations, the uncharged compounds, I and phenyl acetate, have the highest turnover rates.

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