Polyamine metabolism I: synthesis of dansyl derivatives of N (monoaminoalkyl) and N (polyaminoalkyl)acetamides and elucidation in urine of a cancer patient

Article abstract of DOI:10.1002/jps.2600660810

The dansyl derivatives of N-(monoaminoalkyl)- and N-(polyaminoalkyl)acetamides were synthesized and unequivocally characterized. TLC of the dansyl derivatives obtained from human urine indicated the presence of N-[3-[(4-aminobutyl)amino]propyl]acetamide (N¹-acetylspermidine), N-[4-[(3-aminopropyl)amino]butyl]acetamide (N⁸-acetylspermidine), and N-(4-aminobutyl)acetamide (N-acetylputrescine) in appreciable amounts. The dansyl derivatives of N¹-acetylspermidine, N⁸-acetylspermidine, and N-acetylputrescine were isolated and purified using various chromatographic methods. The mass spectra of these compounds were similar to those of authentic samples, which confirmed the identity of these compounds and established the presence of N⁸-acetylspermidine as well as N¹-acetylspermidine and N-acetylputrescine in human urine.