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

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. Here...

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Bibliographic Details
Published in:Organic letters 2021-09, Vol.23 (18), p.7106-7111
Main Authors: Kuranaga, Takefumi, Tamura, Miho, Ikeda, Hiroaki, Terada, Sakahiro, Nakagawa, Yusuke, Kakeya, Hideaki
Format: Article
Language:English
Subjects:
Actinomycetales - chemistry
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - chemistry
Anti-Bacterial Agents - pharmacology
Macrolides - chemical synthesis
Macrolides - chemistry
Macrolides - pharmacology
Molecular Structure
Protein Synthesis Inhibitors - chemistry
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c02506