炭水化物系化合物の自動酸化分解 : 第2報 Glucoseよりアラボン酸生成の新ルート その2
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When an ethanol solution, in which were dissolved N-aryl-glucosylamine (I) (1 mole) and arylamine (1-1.5 mole) was allowed to stand at room temperature, N, N'-diarylform-amidine salt of D-arabonic acid (III) was initially precipitated (after 1-2 weeks). Secondly 1-aryl-benzimidazol (VI) (VIa, 4' : CH_3,6 : CH_3 VIb, 4' : OCH_3,6 : OCH_3) and N, N'-diaryloxalamide (VII) were precipitated after a lapse of 30 to 60 days. Finally N, N'-diarylurea (VIII) and azobenzene derivative (IX) were deposited after 40 to 80 days' keep standing. Deposits were all seperated from the residual solution, ethanol being evaporated. The remaining non-volatile residue was extracted with boiling water, and N-aryl-D-arabonamide (IV) was obtained as a water soluble fraction. Similarly, by allowing to stand at room temperature, III, IV, VI and VII were also obtained from the ethanol solution of arylamine and 1-deoxy-1-arylamino-D-fructose (II), Amadori rearranged compound, derived from I. Carbon chain of glucose is decomposed fragmentally at the bond C_1-C_2 to give arabonic acid formed from the bond C_2-C_6. By the reaction of arylamine with the fragment C_1 separated from the bond C_1-C_6 of glucose, V, VI, VII and VIII are formed by autoxidation free radically. In the basic ethanol solution of arylamine, the reaction of II with arylamine may possibly proceed in the reverse course to Amadori rearrangement, and the hydrogen at C_3 of enaminol (Chart 3), which appears in both courses, is pulled out to form free radical X_1. By the intramolecular rearrangement, X is formed from X_1. Thus the peroxide begins to initiate the decomposition between C_1-C_2 of X.
- 公益社団法人日本薬学会の論文
- 1968-09-25
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