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

Author

Listed:
  • Shupeng Yin

    (Ocean University of China)

  • Zhi Liu

    (Ocean University of China
    Pilot National Laboratory for Marine Science and Technology (Qingdao))

  • Jingjing Shen

    (Ocean University of China
    Pilot National Laboratory for Marine Science and Technology (Qingdao))

  • Yuwei Xia

    (Ocean University of China
    Pilot National Laboratory for Marine Science and Technology (Qingdao))

  • Weihong Wang

    (Ocean University of China)

  • Pengyan Gui

    (Ocean University of China)

  • Qian Jia

    (Ocean University of China)

  • Konthorn Kachanuban

    (Ocean University of China
    Kasetsart University)

  • Weiming Zhu

    (Ocean University of China
    Pilot National Laboratory for Marine Science and Technology (Qingdao))

  • Peng Fu

    (Ocean University of China
    Pilot National Laboratory for Marine Science and Technology (Qingdao))

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.

Suggested Citation

  • Shupeng Yin & Zhi Liu & Jingjing Shen & Yuwei Xia & Weihong Wang & Pengyan Gui & Qian Jia & Konthorn Kachanuban & Weiming Zhu & Peng Fu, 2022. "Chimeric natural products derived from medermycin and the nature-inspired construction of their polycyclic skeletons," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-32901-0
    DOI: 10.1038/s41467-022-32901-0
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    References listed on IDEAS

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    1. Yu Zong & Fang Fang & Kirsten J. Meyer & Liguo Wang & Zhihao Ni & Hongying Gao & Kim Lewis & Jingren Zhang & Yu Rao, 2019. "Gram-scale total synthesis of teixobactin promoting binding mode study and discovery of more potent antibiotics," Nature Communications, Nature, vol. 10(1), pages 1-11, December.
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