Syntheses of crowned polyamines using isolable succinimidyl esters of N-tritylated linear amino acids and peptides

Partial and total syntheses of polyamines incorporating crown ether moieties have been effected using N-tritylated linear amino acids, like beta-alanine (betaAla) and gamma-aminobutyric acid (gammaAba), to introduce the N-3-C and N-4-C polyamine structural units, respectively. The partial syntheses involve the acylation of commercially available crown bearing amino function(s) or aza-oxa crown ethers with the isolable succinimidyl esters of Trt-betaAla-OH or Trt-betaAla-gammaAba-OH, followed by LiAlH4-mediated reduction of the resulting amides, whereas in the total syntheses the crown and the aza-oxa crown ether moieties are built-up from commercially available starting materials like polyethylene glycols, epichlorohydrin and dibenzylamine.