Synthesis of 13C-dilabeled 4-coumaroylspermidines

Article abstract of DOI:10.1016/S0040-4020(98)01014-X

Five ¹³C-dilabeled constitution isomers of 4-coumaroylspermidines were prepared in nine to eleven steps: N¹,4-di[(E)-4-coumaroyl]-(5,8- ¹³C₂)spermidine (13b), N¹-[(E)-4-coumaroyl]-(5,8-¹³C₂)spermidine (17b), N¹,8-di[(E)-4-coumaroyl]-(1,4-¹³C₂)spermidine (20b), N⁴-[(E)-4- coumaroyl]-(1,4-¹³C₂)spermidine (24b) and N¹,4,8-tri[(E)-4-coumaroyl]- (5,8-¹³C2)spermidine (26). The two ¹³C-atoms were subsequently introduced using labeled potassium cyanide. The synthesis proceeds through stepwise construction of the polyamine backbone including protection and deprotection steps of the amino functions. Based on ¹H-¹H NOE interactions, the preliminary study of their binding reveals that 20b binds to tRNA in the same way as spermidine does, whereas 24b and 26 do not show any NOE effects with the tRNA protons.