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

Abstract

Partial and total syntheses of polyamines incorporating crown ether moieties have been effected using N-tritylated linear amino acids, like β-alanine (βAla) and γ-aminobutyric acid (γAba), 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-βAla-OH or Trt-βAla-γAba-OH, followed by LiAlH 4-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.