Glutathione in the noncanonical biosynthesis of teredinibactins

19 November 2024, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Teredinibactins are ß-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 me-tabolites in a noncanonical peptide azoline pathway. 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.

Keywords

biosynthesis
total synthesis
thiazoline
secondary metabolites

Supplementary materials

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Supporting Information for "Glutathione in the noncanonical biosynthesis of teredinibactins"
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Methods, chemical characterization, synthetic schemes, and analytical data supporting the main publication.
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