ChemInform Abstract: Probing the Specificity of the Serine Proteases Subtilisin Carlsberg and α-Chymotrypsin with Enantiomeric 1-Acetamido Boronic Acids. An Unexpected Reversal of the Normal “L”-Stereoselectivity Preference.
Abstract
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ChemInform Abstract
Both enantiomers (VI) are prepared as is demonstrated for the (R)- series starting with the homologation of the corresponding pinanediol esters. The α-chloroboronic compounds are obtained with diastereoselectivities >98%. All of the boronic acids are powerful competitive inhibitors of both title enzymes with the L-enantiomers being generally more potent than the D-enantiomers. However, a great reversal of the normal stereoselectivity preference is observed in the inhibition of α-chymotrypsin by (VId).
