Synthesis of 9-Dechlorochrysophaentin A Enables Studies Revealing Bacterial Cell Wall Biosynthesis Inhibition Phenotype in B. subtilis,Journal of the American Chemical Society

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Synthesis of 9-Dechlorochrysophaentin A Enables Studies Revealing Bacterial Cell Wall Biosynthesis Inhibition Phenotype in B. subtilis
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2020-08-31 , DOI: 10.1021/jacs.0c04917
Christopher R Fullenkamp ₁ , Yen-Pang Hsu _{2,

3} , Ellen M Quardokus ₂ , Gengxiang Zhao ₄ , Carole A Bewley ₄ , Michael VanNieuwenhze _{2,

3} , Gary A Sulikowski _{1,

5,

6}

Affiliation

Chrysophaentin A is an antimicrobial natural product isolated from the marine alga C. taylori in milligram quantity. Structurally, chrysophaentin A features a macrocyclic biaryl ether core incorporating two trisubstituted chloroalkenes at its periphery. A concise synthesis of iso- and 9-dechlorochrysophaentin A enabled by a Z-selective RCM cyclization followed by an oxygen to carbon ring contraction is described. Fluorescent microscopy studies revealed 9-dechlorochrysophaentins leads to inhibition of bacterial cell wall biosynthesis by disassembly of key divisome proteins, the cornerstone to bacterial cell wall biosynthesis and division.

中文翻译：

9-Dechlorochrysophaentin A 的合成使研究能够揭示枯草芽孢杆菌中的细菌细胞壁生物合成抑制表型

Chrysophaentin A 是一种从海藻 C. taylori 中以毫克量分离的抗菌天然产物。在结构上，chrysophaentin A 具有一个大环联芳醚核，在其外围结合了两个三取代的氯代烯烃。描述了通过 Z 选择性 RCM 环化和氧到碳环收缩实现的异和 9-脱氯金黄素 A 的简明合成。荧光显微镜研究表明，9-dechlorochrysophaentins 通过分解关键的二分体蛋白（细菌细胞壁生物合成和分裂的基石）来抑制细菌细胞壁的生物合成。

更新日期：2020-08-31

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