炭水化物系化合物の自動酸化分解(第4報) : Glucoseの自動酸化分解によるシュウ酸の生成

概要

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N-p-Tolyl-D-glucosylamine (GPT). and N-p-anisyl-D-glucosylamine. (GPA) were cleaved autoxidatively in ethanol solution containing p-toluidine and p-anisidine, respectively, and N, N'-diarylformamidine salt of D-arabonic acid (III), N-aryl-D-arabonamide (IV), N, N'-diaryloxalamide (V), and 1-aryl-2-aryliminomethylbenzimidazoloe (VI) were isolated. These N-aryl-D-glucosylamines reacted with benzylamine and cyclohexylamine, and IV and V were formed, but not III and VI. The results obtained here indicate that oxalic acid is easily formed by C-chain cleavage of sugars. GPT[1-^<14>C], GPT[2-^<14>C], N-cyclohexyl-D-glucosylamine[1-^<14>C] and N-cyclohexyl-D-glucosylamine[2-^<14>C] were cleaved in contact with p-toluidine or cyclohexylamine, and oxalamides (V) were isolated. The results of ^<14>C incorporation into these decomposed products indicate that C-1 and C-2 of glucose were containted in oxalic acid and N-aryl-D-glucosylamine in which RNH_2 bonded was decomposed by free amine R_1NH_2,and three types of oxalamide [chemical formula] were isolated. These results indicate that there are two routes for the formation of oxalic acid ; one is the cleavage of C_2-C_3 bond in glucose, and the other, the cleavage of C_1-C_2 bond and polymerization of C_1 fragment.
公益社団法人日本薬学会の論文
1969-11-25