Syntheses of [5,8-^<13>C_2]- and [1,12-<13>C_2]Spermine Using Potassium [^<13>C]Cyanide as the ^<13>C Source

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[5,8-^<13>C_2]Spermine and [1,12-^<13>C_2]spermine were prepared using [^<13>C]KCN as the source of the label. By reaction of the latter with 1,2-dibromoethane and ethylene chlorohydrin, the corresponding [1,4-^<13>C_2]succinodinitrile and [CN-^<13>C]ethylene cyanohydrin were respectively obtained. The reaction conditions were carefully adjusted so as to optimize the yields of the ^<13>C-enriched intermediates. The nitrile residues were then reduced using sodium trifluoroacetoxyborohydride in tetrahydrofuran. [1,4-^<13>C_2]Putrescine and [3-^<13>C]3-aminopropanol were thus obtained. The latter was transformed into its [3-^<13>C]3-carbobenzyloxyamidopropyl bromide derivative. The syntheses of [5,8-^<13>C_2]spermine from the [1,4-^<13>C_2]putrescine precursor and N-(3-bromopropyl)phthalimide, and of [1,12-^<13>C_2]spermine from N, N'-bisbenzylputrescine and the [3-^<13>C]3-carbobenzyloxyamidopropyl bromide precursor were then carried out using our previously reported methods, which were modified so as to maximize the yields of the ^<13>C-enriched products.
社団法人日本薬学会の論文
1995-11-15