The synthesis of deuterium-labeled spermine, N-acetylspermine and N-acetylspermidine.

The synthesis of deuterium labeled spermine, N(1)-acetylspermine and N(1)-acetylspermidine is reported. 1,1,3,3-(2)H(4)-N(1)-Acetylspermine hydrochloride, 1,1,3,3-(2)H(4)-N(1)-acetylspermidine hydrochloride and 1,1,3,3,10,10,12,12-(2)H(8)-spermine dihydrochloride were obtained in seven, four and three steps respectively. All the syntheses were carried out by simple protection and deprotection steps from commonly used selective protecting reagents. These deuterium labeled compounds can be used as mechanistic probes of polyamine oxidizing enzymes.