IDEAS home Printed from https://ideas.repec.org/a/nat/natcom/v13y2022i1d10.1038_s41467-022-32641-1.html
   My bibliography  Save this article

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
    as

    Download full text from publisher

    File URL: https://www.nature.com/articles/s41467-022-32641-1
    File Function: Abstract
    Download Restriction: no

    File URL: https://libkey.io/10.1038/s41467-022-32641-1?utm_source=ideas
    LibKey link: if access is restricted and if your library uses this service, LibKey will redirect you to where you can use your library subscription to access this item
    ---><---

    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.
    Full references (including those not matched with items on IDEAS)

    Citations

    Citations are extracted by the CitEc Project, subscribe to its RSS feed for this item.
    as


    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.

    Most related items

    These are the items that most often cite the same works as this one and are cited by the same works as this one.
    1. Yuchun Zhao & Xiangyang Liu & Zhihong Xiao & Jie Zhou & Xingyu Song & Xiaozheng Wang & Lijun Hu & Ying Wang & Peng Sun & Wenning Wang & Xinyi He & Shuangjun Lin & Zixin Deng & Lifeng Pan & Ming Jiang, 2023. "O-methyltransferase-like enzyme catalyzed diazo installation in polyketide biosynthesis," Nature Communications, Nature, vol. 14(1), pages 1-14, December.
    2. Ghader Bashiri & Esther M. M. Bulloch & William R. Bramley & Madison Davidson & Stephanie M. Stuteley & Paul G. Young & Paul W. R. Harris & Muhammad S. H. Naqvi & Martin J. Middleditch & Michael Schmi, 2024. "Poly-γ-glutamylation of biomolecules," Nature Communications, Nature, vol. 15(1), pages 1-11, December.
    3. 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.

    More about this item

    Statistics

    Access and download statistics

    Corrections

    All material on this site has been provided by the respective publishers and authors. You can help correct errors and omissions. When requesting a correction, please mention this item's handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-32641-1. See general information about how to correct material in RePEc.

    If you have authored this item and are not yet registered with RePEc, we encourage you to do it here. This allows to link your profile to this item. It also allows you to accept potential citations to this item that we are uncertain about.

    If CitEc recognized a bibliographic reference but did not link an item in RePEc to it, you can help with this form .

    If you know of missing items citing this one, you can help us creating those links by adding the relevant references in the same way as above, for each refering item. If you are a registered author of this item, you may also want to check the "citations" tab in your RePEc Author Service profile, as there may be some citations waiting for confirmation.

    For technical questions regarding this item, or to correct its authors, title, abstract, bibliographic or download information, contact: Sonal Shukla or Springer Nature Abstracting and Indexing (email available below). General contact details of provider: http://www.nature.com .

    Please note that corrections may take a couple of weeks to filter through the various RePEc services.

    IDEAS is a RePEc service. RePEc uses bibliographic data supplied by the respective publishers.