Preferential Acid-catalyzed Hydrolysis of the Formamide Linkage of N'-Formylkynurenine in Frozen Solution

Abstract

Acid-catalyzed hydrolysis of the formamide linkage of N-acetyl-N'-formyl-L-kynurenineamide in frozen dilute hydrochloric acid solution followed first-order kinetics, yielding N-acetyl-L-kynurenineamide as the sole reaction product. The maximum rate of reaction in the frozen solution was found at around -7.5° and approximated that of the reaction in liquid solution at 40°. By freezing the dilute acid solution at -8° the reaction was accelerated by 60 times compared with that in super-cooled liquid solution at the same temperature.