Work

Systematic Investigation on Acid-Catalyzed Truncation of N-Acylated Peptoids

Year: 2024

Type: article

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.

Source: International Journal of Molecular Sciences

DOI: 10.3390/ijms252111390

Authors: Ruiqi Piao, Yong-Uk Kwon

Institution: Ewha Womans University

Language: English

Topic: Chemical Synthesis and Analysis

Subfield: Molecular Biology

Field: Biochemistry, Genetics and Molecular Biology

Domain: Life Sciences

Open Access status: gold

Estimated APC paid: $3,296

Funders: National Research Foundation, National Research Foundation of Korea, Ministry of Science and ICT, South Korea