A versatile entry to unnatural, disulfide-linked amino acids and peptides through the disulfuration of azlactones.

ABSTRACT: Despite the evident demand and promising potential of disulfide-functionalized amino acids and peptides in linker chemistry and peptide drug discovery, those disulfurated specifically at the α-position constitute a unique yet rather highly underexplored chemical space. In this study, we have developed a method for preparing SS-linked amino acid/peptide derivatives through a base-catalyzed disulfuration reaction of azlactones, followed by the ring-opening functionalization. The disulfuration reaction proceeds under mild conditions, yielding disulfurated azlactones in excellent yields across a variety of N-dithiophthalimides and diverse azlactones derived from various amino acids and peptides. Leveraging the ready availability of N-dithiophthalimides from several bilater

SUBMITTER: Iwata M 

PROVIDER: S-EPMC11726236 | biostudies-literature | 2025 Feb

REPOSITORIES: biostudies-literature