Abstract
The enantioselectivity for the subtilisin-catalyzed hydrolysis of ethyl (RS)-2-(4-substituted phenoxy)propionates in aqueous buffer was found to be improved by the addition of dimethyl sulfoxide (DMSO). On the basis of the conformational change of subtilisin Carlsberg observed by FT-IR, CD, and fluorescence spectra, the DMSO-induced high enantioselectivity could be related to a partial decrease of subtilisin's tertiary structure. This model for the subtilisin's enantiorecognition is also supported by analysis of the specific catalytic constants (Vmax/Km) obtained for each enantiomer of the substrate. In addition, substituent effects on the enantioselectivity for the subtilisin-catalyzed hydrolysis were studied by use of a range of ethyl (RS)-2-(4-substituted phenoxy)propionates as substrates.
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