Work

Optimized Monomer-Based Synthesis of Poly-N-amino Peptides

Year: 2025

Type: article

Abstract: We report an optimized protocol for the solid-phase synthesis of backbone-N-aminated peptides. Electrophilic N-amination of amino acid zwitterions provides crude -hydrazino acids that can be used directly in SPPS. In situ formation of Fmoc-protected amino acid chlorides with Ghosez’s reagent enables base-free couplings to -hydrazino acids on an automated system. TFA-free cleavage and global deprotection affords poly-N-amino peptides in high crude purity and in a fraction of the time required by previously reported methods.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.5c00247

Authors: Avraz F. Anwar, Juan R. Del Valle

Institution: University of Notre Dame

Language: English

Topic: Chemical Synthesis and Analysis

Subfield: Molecular Biology

Field: Biochemistry, Genetics and Molecular Biology

Domain: Life Sciences

Open Access status: green

Funders: National Institutes of Health, National Institute on Aging, Division of Chemistry

Awards: G2272136557, Chemistry-Biochemistry-Biology Interface (CBBI) Program at Notre Dame, Chemical approaches to selectively target beta-rich amyloids