Building units for N-backbone cyclic peptides. 2. Synthesis of protected N-(ω-thioalkylene) amino acids and their incorporation into dipeptide units

Article abstract of DOI:10.1016/0040-4020(95)00663-S

A new family of amino acids which contain an ω-thioalkylene group on the N(α)-amino nitrogen was synthesized by alkylation of ω-thioalkylamines with triflates of α-hydroxy acids. The reaction proceeded with inversion of configuration yielding optically pure products. The N(α)-(ω-thioalkylene)amino acids were orthogonally protected to allow their incorporation into peptides by solid-phase peptide synthesis (SPPS) methodology. In addition some of these new protected N(α)-(ω-thioalkylene)amino acids were incorporated into dipeptides by 'solution' techniques.