反応経過の検討と反応中間体の推定構造 (アルミニウムアマルガムによるストレプトマイシンの還元に関する研究-1,2-)

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The progress of reduction of streptomycin (SM) with aluminum amalgam, which finally produces dihydrodeoxystreptomycin (DDS) was pursued by combination of analytical methods developed for this study. It was made clear that DDS is the reduction product of an unknown reaction intermediate. Based on the previous results and the consideration of the rate process, it was concluded that this intermediate is produced by the reduction of streptomycin at the tertiary hydroxyl group on C-3 of streptose: i.e., its structure presumed to be 1-(1, 3-diguanido-2, 4, 5, 6-tetrahydroxycyclohexanido)-2-(N-methyl-α-L-glucopyranosido)-3-C-formyl-3, 5-dideoxy-α-L-pentofuranose. This intermediate product may be termed deoxystreptomycin (DOS).
社団法人日本農芸化学会の論文