Modular Synthesis of the Potent Antibiotic Amycolamicin and Diastereomeric Analogues Thereof

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2025-04-02 DOI:10.1021/acs.orglett.5c00742

Xuejian Yin, Zhengxuan Zhang, Ziqi Yuan, Qiuyu Zhu, Peng Xu, Cai-Guang Yang, Dapeng Zhu, Biao Yu

引用次数: 0

Abstract

A modular approach to the potent, broad-spectrum antibiotic amycolamicin and seven diastereomeric analogues is described. The synthesis features bioinspired construction of the high-carbon amycolose segment, gold(I)-catalyzed high-yielding O-glycosylation of the trans-decalin scaffold, N-glycosylation of the bromoacetylated l-valine derivative, and condition-tuned late-stage C-acylation of the tetramic acid motif. An assessment of the antibacterial properties of these synthetic molecules indicated that the correct stereochemistry is essential for the potent bioactivity of amycolamicin.

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强效抗生素氨基嘧啶及其非对映异构体的模块化合成

模块化的方法有效，广谱抗生素淀粉霉素和七个非对映异构体类似物被描述。该合成具有生物启发结构的高碳淀粉段，金(I)催化的反式十氢化萘支架的高产o糖基化，溴乙酰化的l-缬氨酸衍生物的n糖基化，以及条件调节的四羧酸基序的后期c酰化。对这些合成分子的抗菌性能的评估表明，正确的立体化学对amycolamicin的有效生物活性至关重要。

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.

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