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The aldehyde inhibitor Z-Ala-Ala-Phe-CHO has been synthesized and shown by 13 C-NMR to react with the active site serine hydroxyl group of alpha-chymotrypsin to form two diastereomeric hemiacetals. For both hemiacetals oxyanion formation occurs with a pK a value of ~7 showing that chymotrypsin reduces the oxyanion pK a values by ~5.6 pK a units and stabilizes the oxyanions...
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