Identification and Total Synthesis of an Unstable Anticancer Macrolide Presaccharothriolide Z Produced by Saccharothrix sp. A1506,Organic Letters

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Identification and Total Synthesis of an Unstable Anticancer Macrolide Presaccharothriolide Z Produced by Saccharothrix sp. A1506
Organic Letters ( IF 4.9 ) Pub Date : 2021-08-26 , DOI: 10.1021/acs.orglett.1c02506
Takefumi Kuranaga ₁ , Miho Tamura ₁ , Hiroaki Ikeda ₁ , Sakahiro Terada ₁ , Yusuke Nakagawa ₁ , Hideaki Kakeya ₁

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Saccharothriolides A–F are 10-membered microbial macrolides proposed to be generated from their precursors presaccharothriolides X–Z. Previously, we isolated presaccharothriolide X, and its unique natural prodrug-like properties have intrigued us. However, the other congeners were not detected. Herein, we detected presaccharothriolide Z using our highly sensitive labeling reagent. Moreover, chemical synthesis of presaccharothriolide Z, the first total synthesis of saccharothriolide-class macrolides, was achieved, and the structure and biological activity of presaccharothriolide Z were determined.

中文翻译：

Saccharothrix sp. 生产的不稳定抗癌大环内酯 Presaccharothriolide Z 的鉴定和全合成 A1506

Saccharothriolides A-F 是 10 元微生物大环内酯类，建议由其前体 presaccharothriolides X-Z 产生。此前，我们分离出前糖三内酯 X，其独特的天然前药样特性引起了我们的兴趣。然而，没有检测到其他同系物。在这里，我们使用我们的高灵敏度标记试剂检测到 presaccharothriolide Z。此外，还实现了糖三内酯类大环内酯类首个全合成的前糖三内酯Z的化学合成，并确定了前糖三内酯Z的结构和生物活性。

更新日期：2021-09-17

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