Horse liver alcohol dehydrogenase-catalyzed enantioselective reduction of cyclic ketones: The effect of the hydrophobic side chain of the substrate on the stereoselectivity of the reaction

Horse liver alcohol dehydrogenase (HLADH)-catalyzed enantioselective reductions of alkyl 3-oxocyclopentanecarboxylates, endo-5-acyloxybicyclo2.2.1]heptan-2-ones and exo-5-acyloxybicyclo2.2.1]heptan-2-ones gave the corresponding homochiral alcohols and ketones and the interaction between the hydrophobic side chain of the substrate and the hydrophobic zone in the active site played an important role in the specificity of the reduction. The stereoselectivities of the reactions were interpreted on the basis of the cubic space section model and a new rule, which contributes to development of a specificity analysis on the basis of the model, is introduced.