Chimeric natural products derived from medermycin and the nature-inspired construction of their polycyclic skeletons

Shupeng Yin, Zhi Liu, Jingjing Shen, Yuwei Xia, Weihong Wang, Pengyan Gui, Qian Jia, Konthorn Kachanuban, Weiming Zhu () and Peng Fu ()
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Shupeng Yin: Ocean University of China
Zhi Liu: Ocean University of China
Jingjing Shen: Ocean University of China
Yuwei Xia: Ocean University of China
Weihong Wang: Ocean University of China
Pengyan Gui: Ocean University of China
Qian Jia: Ocean University of China
Konthorn Kachanuban: Ocean University of China
Weiming Zhu: Ocean University of China
Peng Fu: Ocean University of China

Nature Communications, 2022, vol. 13, issue 1, 1-9

Abstract: Abstract Medermycin, produced by Streptomyces species, represents a family of antibiotics with significant activity against Gram-positive pathogens. The biosynthesis of this family of natural products has been studied, and new skeletons related to medermycin have rarely been reported until recently. Herein, we report eight chimeric medermycin-type natural products with unusual polycyclic skeletons. The formation of these compounds features some key nonenzymatic steps, which inspired us to construct complex polycyclic skeletons via three efficient one-step reactions under mild conditions. This strategy was further developed to efficiently synthesize analogues for biological activity studies. The synthetic compounds, chimedermycins L and M, and sekgranaticin B, show potent antibacterial activity against Staphylococcus aureus, methicillin-resistant Staphylococcus aureus, and methicillin-resistant Staphylococcus epidermidis. This work paves the way for understanding the nonenzymatic formation of complex natural products and using it to synthesize natural product derivatives.

Date: 2022
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DOI: 10.1038/s41467-022-32901-0

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