Sung Youjung, Miller Bailey W, Schmidt Eric W
Department of Medicinal Chemistry, University of Utah, Salt Lake City, Utah 84112, United States.
Org Lett. 2025 Feb 28;27(8):1774-1778. doi: 10.1021/acs.orglett.4c04336. Epub 2025 Feb 17.
Teredinibactins are β-resorcyclic thiazoline dipeptides synthesized by 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.
船蛆菌素是由海洋船蛆的细菌共生体T7901合成的β-间苯二酚噻唑啉二肽。通过喂养研究,我们表明噻唑啉部分是由谷胱甘肽及其代谢物通过一条非经典途径形成的,我们建议将其命名为“谷氨唑啉”。模仿生物合成反应,我们合成了天然和非天然的船蛆菌素。这些结果扩展了制备芳香唑啉共轭物的生物学和化学方法的范围。