放線菌抗生物質の化学的研究 (第5報)

Aquamycinの構造

抄録

A strain of Actinomyces isolated from a soil in Cambodia was found by one (Funaki) of the authors to be a new strain not reported in any literature and this was named Streptomyces reticuli var. aquamyceticus. The antibiotic produced by this strain was named Aquamycin, which was found to be effective against Erhlich carcinoma. The structure of this antibiotic was clarified in the present series of work and the structure was confirmed by its synthesis. The ultraviolet and infrared spectra of Aquamycin (I), C₄H₄O₂N₂, suggested the presence of amide-I and conjugated unsaturated carbonyl. Catalytic reduction of (I) afforded a tetrahydro compound (II), C₄H₈O₂N₂, and its saponification with potassium hydroxide gave succinic acid. Consequently, (II) was assumed to be succinamide and this was identified with an authentic sample. Direct saponification of (I) afforded C₄H₂O₄ (IV) which was identified with acetylenedicarboxylic acid obtained from dibromosuccinic acid. From these results, (I) was assumed to be acetylenedicarboxamide but constants of (I) differed slightly from those listed in the literature. Further reexamination of synthetic routes was made and comparison of (I) and synthesized product showed that they agreed in decomposition point, elemental analytical values, and ultraviolet and infrared spectra, thereby confirming the structure of Aquamycin to be acetylene-dicarboxamide.