Chemoselective Modification of Reducing 2‑Acetamido Sugars Enables Facile Functionalization of Diverse Peptidoglycan Fragments Derived from the Gut Microbiota.

ABSTRACT: Gut microbiota-derived peptidoglycan fragments (PGNs) are key signaling molecules in microbiota-host crosstalk. Efficient strategies to functionalize natural, unprotected PGN molecules are highly desirable for advancing the biological studies of PGNs. In this work, we developed a facile chemoselective strategy to derivatize the anomeric C1 position of reducing 2-acetamido sugars, a characteristic shared by most PGNs that contain reducing N-acetylmuramic acid. Upon treatment with imidazole-dithiocarbamate-azide (IDA), we showed that natural reducing 2-acetamido PGNs are readily converted to oxazoline intermediates under aqueous conditions. Serendipitously, we discovered that simply freeze-drying the reaction mixture promotes glycosidation of the oxazoline glycosyl donor, leadi

SUBMITTER: Adamson C 

PROVIDER: S-EPMC12457995 | biostudies-literature | 2025 Sep

REPOSITORIES: biostudies-literature