炭水化物系化合物の自動酸化分解(第3報) : GlucoseのC_1-C_2,およびC_2-C_3間の自動酸化分解

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3,4,5,6-Tetrabenzoyl-aldehydo-D-glucose (V) was isolated as white crystals on heating the dioxan solution of 1-deoxy-1,1-di(p-toluidino)-3,4,5,6-tetrabenzoyl-aldehydo-D-glucose (VI) and oxalic acid in nitrogen stream, and 1-deoxy-1-(p-toluidino)-3,4,5,6-tetrabenzoyl-keto-D-fructose (VII) reported by Micheel was not obtained. The results obtained here are in favor of the report of Weygand and of Isbell that Amadori rearrangement took route A as shown in Chart 1 and enaminol was an intermediate. N-(p-Tolyl)-D-glucosylamine-[1-^<14>C] and N-(p-tolyl)-D-glucosylamine-[2-^<14> C] were cleaved oxidatively in contact with p-toluidine and N, N'-di(p-tolyl)formamidine salt of D-arabonic acid (III), N, N'-di(p-tolyl)formamidine (IIIf), 1-(p-tolyl)-2,6-dimethylbenzimidazole (VIII), and p-tolylarabonamide (IX) were isolated. The results of ^<14> C incorporation into these decomposed products indicated that (1) the cleavage of C_1-C_2 bond of glucose gave formamidine and arabonic acid which were formed from C_1 or C_2-C_6 fragment, respectively. (2) Benzimidazole was not formed from formamidine, but from C_1-C_2 fragment formed as a result of C_2-C_3 bond cleavage.
公益社団法人日本薬学会の論文
1969-11-25