Complementary Strategies for Installation of Thioimidates into Peptide Backbones.

ABSTRACT: Thioimidates are a precursor and synthetic branch point to access either thioamide or amidine isosteres of the native amide (peptide bond). Previous syntheses of thioimidate-containing peptides were prone to side reactivity and required slow, cumbersome steps that were difficult to monitor. We describe a more efficient approach to directly couple thioimidates onto the growing peptide chain. This work also outlines optimal conditions for thioimidate formation on solid support and identifies potential off-target sites for alkylation that impact the choice of protecting group.

SUBMITTER: Byerly-Duke J 

PROVIDER: S-EPMC11894813 | biostudies-literature | 2024 Oct

REPOSITORIES: biostudies-literature