{"title":"Total Synthesis of LL-A0341β1","authors":"Lindsey Shivers, Jeremy Goodyear, Scott D. Taylor","doi":"10.1021/acs.orglett.4c04487","DOIUrl":null,"url":null,"abstract":"The first total synthesis of cyclic depsipeptide antibiotic LL-A0341β<sub>1</sub> (LL) is described. The configuration of the β-methyltryptophan (β-MeTrp) residue was established by preparing all four stereoisomers of Fmoc-β-MeTrp which were used for the synthesis of LL via Fmoc solid phase peptide synthesis. The most active of the four peptides was the one containing (2<i>R</i>,3<i>R</i>)-β-MeTrp. The activity of LL was strongly inhibited by cardiolipin (CL), but not other common phospholipids found in bacterial cell membranes, suggesting that LL interacts with CL in the lipid membrane.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"153 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2025-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.4c04487","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
The first total synthesis of cyclic depsipeptide antibiotic LL-A0341β1 (LL) is described. The configuration of the β-methyltryptophan (β-MeTrp) residue was established by preparing all four stereoisomers of Fmoc-β-MeTrp which were used for the synthesis of LL via Fmoc solid phase peptide synthesis. The most active of the four peptides was the one containing (2R,3R)-β-MeTrp. The activity of LL was strongly inhibited by cardiolipin (CL), but not other common phospholipids found in bacterial cell membranes, suggesting that LL interacts with CL in the lipid membrane.
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.
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