Total Synthesis of LL-A0341β1

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2025-01-02 DOI:10.1021/acs.orglett.4c04487

Lindsey Shivers, Jeremy Goodyear, Scott D. Taylor

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.

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l - a0341 β的全合成

报道了环沉积肽抗生素LL- a0341 β1 （LL）的首次全合成。通过制备Fmoc-β-MeTrp的四个立体异构体，确定了β-甲基色氨酸（β-MeTrp）残基的构型，这些异构体用于Fmoc固相肽合成LL。四种肽中活性最高的是含有(2R,3R)-β-MeTrp的肽。心磷脂（cardiolipin， CL）对LL的活性有较强的抑制作用，而其他常见的细菌细胞膜磷脂对LL的活性没有抑制作用，提示LL与脂质膜中的CL相互作用。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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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.