Syntheses of (5,8-l3C2)- and (1,12-l3C2)Spermine Using Potassium (l3C)Cyanide as the 13C Source.

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Abstract
[5, 8-13C2]Spermine and [1, 12-13C2]spermine were prepared using [13C]KCN as the source of the label. By reaction of the latter with 1, 2-dibromoethane and ethylene chlorohydrin, the corresponding [1, 4-13C2]succinodinitrile and [CN-13C]ethylene cyanohydrin were respectively obtained. The reaction conditions were carefully adjusted so as to optimize the yields of the 13C-enriched intermediates. The nitrile residues were then reduced using sodium trifluoroacetoxyborohydride in tetrahydrofuran. [1, 4-13C2]Putrescine and [3-13C]3-aminopropanol were thus obtained. The latter was transformed into its [3-13C]3-carbobenzyloxyamidopropyl bromide derivative. The syntheses of [5, 8-13C2]spermine from the [1, 4-13C2]putrescine precursor and N-(3-bromopropyl)phthalimide, and of [1, 12-13C2]spermine from N, N'-bisbenzylputrescine and the [3-13C]3-carbobenzyloxyamidopropyl bromide precursor were then carried out using our previously reported methods, which were modified so as to maximize the yields of the 13C-enriched products.

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