Glutathione in the Biosynthesis of Glutazoline Teredinibactins

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-02-17 DOI:10.1021/acs.orglett.4c04336

Youjung Sung, Bailey W. Miller, Eric W. Schmidt

引用次数: 0

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.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.