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Flavin-enabled reductive and oxidative epoxide ring opening reactions

Author

Listed:
  • Bidhan Chandra De

    (Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

  • Wenjun Zhang

    (Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences
    University of Chinese Academy of Sciences
    Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou)
    Sanya Institute of Ocean Eco-Environmental Engineering, Yazhou Scientific Bay)

  • Chunfang Yang

    (Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences
    University of Chinese Academy of Sciences
    Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou)
    Sanya Institute of Ocean Eco-Environmental Engineering, Yazhou Scientific Bay)

  • Attila Mándi

    (University of Debrecen)

  • Chunshuai Huang

    (Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences)

  • Liping Zhang

    (Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences
    University of Chinese Academy of Sciences
    Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou))

  • Wei Liu

    (Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences)

  • Mark W. Ruszczycky

    (University of Texas at Austin)

  • Yiguang Zhu

    (Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences
    University of Chinese Academy of Sciences
    Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou)
    Sanya Institute of Ocean Eco-Environmental Engineering, Yazhou Scientific Bay)

  • Ming Ma

    (Peking University)

  • Ghader Bashiri

    (The University of Auckland)

  • Tibor Kurtán

    (University of Debrecen)

  • Hung-wen Liu

    (University of Texas at Austin)

  • Changsheng Zhang

    (Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences
    University of Chinese Academy of Sciences
    Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou)
    Sanya Institute of Ocean Eco-Environmental Engineering, Yazhou Scientific Bay)

Abstract

Epoxide ring opening reactions are common and important in both biological processes and synthetic applications and can be catalyzed in a non-redox manner by epoxide hydrolases or reductively by oxidoreductases. Here we report that fluostatins (FSTs), a family of atypical angucyclines with a benzofluorene core, can undergo nonenzyme-catalyzed epoxide ring opening reactions in the presence of flavin adenine dinucleotide (FAD) and nicotinamide adenine dinucleotide (NADH). The 2,3-epoxide ring in FST C is shown to open reductively via a putative enol intermediate, or oxidatively via a peroxylated intermediate with molecular oxygen as the oxidant. These reactions lead to multiple products with different redox states that possess a single hydroxyl group at C-2, a 2,3-vicinal diol, a contracted five-membered A-ring, or an expanded seven-membered A-ring. Similar reactions also take place in both natural products and other organic compounds harboring an epoxide adjacent to a carbonyl group that is conjugated to an aromatic moiety. Our findings extend the repertoire of known flavin chemistry that may provide new and useful tools for organic synthesis.

Suggested Citation

  • Bidhan Chandra De & Wenjun Zhang & Chunfang Yang & Attila Mándi & Chunshuai Huang & Liping Zhang & Wei Liu & Mark W. Ruszczycky & Yiguang Zhu & Ming Ma & Ghader Bashiri & Tibor Kurtán & Hung-wen Liu &, 2022. "Flavin-enabled reductive and oxidative epoxide ring opening reactions," Nature Communications, Nature, vol. 13(1), pages 1-13, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-32641-1
    DOI: 10.1038/s41467-022-32641-1
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    References listed on IDEAS

    as
    1. Ghader Bashiri & James Antoney & Ehab N. M. Jirgis & Mihir V. Shah & Blair Ney & Janine Copp & Stephanie M. Stuteley & Sreevalsan Sreebhavan & Brian Palmer & Martin Middleditch & Nobuhiko Tokuriki & C, 2019. "A revised biosynthetic pathway for the cofactor F420 in prokaryotes," Nature Communications, Nature, vol. 10(1), pages 1-12, December.
    2. Bin Wang & Fang Guo & Jinwei Ren & Guomin Ai & Bertrand Aigle & Keqiang Fan & Keqian Yang, 2015. "Identification of Alp1U and Lom6 as epoxy hydrolases and implications for kinamycin and lomaiviticin biosynthesis," Nature Communications, Nature, vol. 6(1), pages 1-5, November.
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    Cited by:

    1. Chunfang Yang & Liping Zhang & Wenjun Zhang & Chunshuai Huang & Yiguang Zhu & Xiaodong Jiang & Wei Liu & Mengran Zhao & Bidhan Chandra De & Changsheng Zhang, 2022. "Biochemical and structural insights of multifunctional flavin-dependent monooxygenase FlsO1-catalyzed unexpected xanthone formation," Nature Communications, Nature, vol. 13(1), pages 1-13, December.

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