チオールエステルに関する研究 (第5報)

抗黴性チオールエステルのアニリンおよびアミノ酸のアミノ基へのアシル基転移反応について

抄録

Antifungal thiol esters and aniline or amino acid were reacted under physiological conditions to presume the mechanism of their antifungal action. Reaction with aniline afforded acyl anilides, same as under organic chemical conditions. Examinations were also made in this reaction on the effect of pH (Table I), effect of additives (Table II), and changes in reactivity of various thiol esters (Table III). Amino acids used were β-alanine, 4-aminobutyric acid, L-histidine, and L-lysine, and their acylated derivatives were isolated for confirmation. Reaction with β-alanine was followed by the Folin and Van Slyke methods (Figs. 1 and 2) and those of L-histidine and L-lysine were followed by paper chromatography. The reaction products of L-lysine with phenyl acetothiolate (or caprothiolate) were submitted to polarography and their polarograms (Figs. 3 and 4) showed that their reduction waves underwent a marked change when reacted for a certain length of time. This was considered to be a valuable datum for presuming the state of acylation with thiol esters in a dilute solution.