Bioinspired one-pot furan-thiol-amine multicomponent reaction for making heterocycles and its applications.

ABSTRACT: One-pot multicomponent coupling of different units in a chemoselective manner and their late-stage diversification has wide applicability in varying chemistry fields. Here, we report a simple multicomponent reaction inspired by enzymes that combines thiol and amine nucleophiles in one pot via a furan-based electrophile to generate stable pyrrole heterocycles independent of the diverse functionalities on furans, thiols and amines under physiological conditions. The resulting pyrrole provides a reactive handle to introduce diverse payloads. We demonstrate the application of Furan-Thiol-Amine (FuTine) reaction for the selective and irreversible labeling of peptides, synthesis of macrocyclic and stapled peptides, selective modification of twelve different proteins with varying payloads, homoge

SUBMITTER: Wang Y 

PROVIDER: S-EPMC10333318 | biostudies-literature | 2023 Jul

REPOSITORIES: biostudies-literature