Teredinibactins are β-resorcyclic thiazoline dipeptides synthesized by Teredinibacter turnerae T7901, a bacterial symbiont of shipworms in the sea. Through feeding studies, we show that the thiazoline moiety is made from… Click to show full abstract
Teredinibactins are β-resorcyclic thiazoline dipeptides synthesized by Teredinibacter turnerae T7901, a bacterial symbiont of shipworms in the sea. Through feeding studies, we show that the thiazoline moiety is made from glutathione and its metabolites in a noncanonical pathway, for which we suggest the name "glutazoline". Mimicking the biosynthetic reaction, we synthesized both natural and unnatural teredinibactins. The results expand the scope of biological and chemical approaches to aromatic azoline conjugates.
Journal Title: Organic letters
Year Published: 2025
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