Latent inhibitors. Part 2. Allylic inhibitors of alcohol dehydrogenase

Abstract

The syntheses of a number of 3-substituted prop-2-en-1-ols and -1-als, required for studying the latent inhibition of horse liver alcohol dehydrogenase (E.C. 1.1.1.1), are described. Substituents were chosen to cover a range of alkoxide, phenolate, thiolate, and halide leaving groups. Of the compounds studied, only 3-ethylthioprop-2-en-1-ol proved to be a latent inhibitor through oxidation to the corresponding aldehyde, catalysed by the enzyme. The persistence of inhibition caused by this inhibitor is shown, by product studies and kinetic measurements, to be due to ethanethiol, formed by an enzyme-catalysed hydrolysis of the aldehyde.