Design, synthesis and characterization of structurally dynamic cyclic N,S-acetals.

ABSTRACT: We report the synthesis, characterization and comparison of a series of electronically perturbed, cyclic N,S-acetals. Inspired by electrophilic auxiliaries utilized for amine capture and concomitant peptide ligation, we studied these N,S-acetal systems and evaluated their propensity to generate zwitterionic intermediates in situ. Certain N,S-acetals in this study exhibit structurally dynamic properties through a solvent and pH-dependent ability to ring-open and ring-close via C1-S bond ionization at room temperature.

SUBMITTER: Kirkeby EK 

PROVIDER: S-EPMC8892990 | biostudies-literature | 2020 Aug

REPOSITORIES: biostudies-literature