Systematic Investigation on Acid-Catalyzed Truncation of <i>N</i>-Acylated Peptoids.

ABSTRACT: Peptoids have emerged as a useful alternative to peptides. However, N-acylated peptoids have occasionally undergone truncation at the terminal peptoid unit under acidic conditions. We previously reported on the mechanistic and electronic aspects of the acid-catalyzed truncation of N-acylated peptoids. To gain further insight, we systematically investigated the conformational and electronic effects of the terminal side chains of peptoids. The n→π* interaction, based on cis/trans-amide bond conformation, is considered to be one of the determining factors. In this study, it was demonstrated that both conformational and electronic factors contribute to this unusual truncation.

SUBMITTER: Piao R 

PROVIDER: S-EPMC11547061 | biostudies-literature | 2024 Oct

REPOSITORIES: biostudies-literature