IDEAS home Printed from https://ideas.repec.org/a/nat/natcom/v15y2024i1d10.1038_s41467-024-52648-0.html
   My bibliography  Save this article

Unspecific peroxygenase enabled formation of azoxy compounds

Author

Listed:
  • Huanhuan Li

    (32 West 7th Avenue
    Xi’an Jiaotong University)

  • Yawen Huang

    (32 West 7th Avenue)

  • Fuqiang Chen

    (32 West 7th Avenue)

  • Zhigang Zeng

    (Hubei University of Science and Technology)

  • Frank Hollmann

    (Delft University of Technology)

  • Xin Wu

    (32 West 7th Avenue)

  • Xiyang Zhang

    (32 West 7th Avenue)

  • Peigao Duan

    (Xi’an Jiaotong University)

  • Hao Su

    (32 West 7th Avenue)

  • Jianjun Shi

    (College of Chemistry and Chemical Engineering Hainan Normal University Haikou)

  • Xiang Sheng

    (32 West 7th Avenue)

  • Wuyuan Zhang

    (32 West 7th Avenue)

Abstract

Enzymes are making a significant impact on chemical synthesis. However, the range of chemical products achievable through biocatalysis is still limited compared to the vast array of products possible with organic synthesis. For instance, azoxy products have rarely been synthesized using enzyme catalysts. In this study, we discovered that fungal unspecific peroxygenases are promising catalysts for synthesizing azoxy products from simple aniline starting materials. The catalytic features (up to 48,450 turnovers and a turnover frequency of 6.7 s–1) and substrate transformations (up to 99% conversion with 98% chemoselectivity) highlight the synthetic potential. We propose a mechanism where peroxygenase-derived hydroxylamine and nitroso compounds spontaneously (non-enzymatically) form the desired azoxy products. This work expands the reactivity repertoire of biocatalytic transformations in the underexplored field of azoxy compound formation reactions.

Suggested Citation

  • Huanhuan Li & Yawen Huang & Fuqiang Chen & Zhigang Zeng & Frank Hollmann & Xin Wu & Xiyang Zhang & Peigao Duan & Hao Su & Jianjun Shi & Xiang Sheng & Wuyuan Zhang, 2024. "Unspecific peroxygenase enabled formation of azoxy compounds," Nature Communications, Nature, vol. 15(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-52648-0
    DOI: 10.1038/s41467-024-52648-0
    as

    Download full text from publisher

    File URL: https://www.nature.com/articles/s41467-024-52648-0
    File Function: Abstract
    Download Restriction: no
    File URL: https://libkey.io/10.1038/s41467-024-52648-0?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. Yuan-Yang Guo & Zhen-Hua Li & Tian-Yu Xia & Yi-Ling Du & Xu-Ming Mao & Yong-Quan Li, 2019. "Molecular mechanism of azoxy bond formation for azoxymycins biosynthesis," Nature Communications, Nature, vol. 10(1), pages 1-9, December.
    2. Zhijun Li & Xiaowen Lu & Cong Guo & Siqi Ji & Hongxue Liu & Chunmin Guo & Xue Lu & Chao Wang & Wensheng Yan & Bingyu Liu & Wei Wu & J. Hugh Horton & Shixuan Xin & Yu Wang, 2024. "Solvent-free selective hydrogenation of nitroaromatics to azoxy compounds over Co single atoms decorated on Nb2O5 nanomeshes," Nature Communications, Nature, vol. 15(1), pages 1-11, December.
    3. Xiaoqiang Huang & Binju Wang & Yajie Wang & Guangde Jiang & Jianqiang Feng & Huimin Zhao, 2020. "Photoenzymatic enantioselective intermolecular radical hydroalkylation," Nature, Nature, vol. 584(7819), pages 69-74, August.
    4. Yitao Dai & Chao Li & Yanbin Shen & Tingbin Lim & Jian Xu & Yongwang Li & Hans Niemantsverdriet & Flemming Besenbacher & Nina Lock & Ren Su, 2018. "Light-tuned selective photosynthesis of azo- and azoxy-aromatics using graphitic C3N4," Nature Communications, Nature, vol. 9(1), pages 1-7, December.
    Full references (including those not matched with items on IDEAS)

    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. Yueshuang Mao & Bingnan Yu & Pengfei Wang & Shuai Yue & Sihui Zhan, 2024. "Efficient reduction-oxidation coupling degradation of nitroaromatic compounds in continuous flow processes," Nature Communications, Nature, vol. 15(1), pages 1-11, December.
    2. Alejandro Prats Luján & Mohammad Faizan Bhat & Sona Tsaturyan & Ronald Merkerk & Haigen Fu & Gerrit J. Poelarends, 2023. "Tailored photoenzymatic systems for selective reduction of aliphatic and aromatic nitro compounds fueled by light," Nature Communications, Nature, vol. 14(1), pages 1-10, December.
    3. Yajun Zou & Sara Abednatanzi & Parviz Gohari Derakhshandeh & Stefano Mazzanti & Christoph M. Schüßlbauer & Daniel Cruz & Pascal Voort & Jian-Wen Shi & Markus Antonietti & Dirk M. Guldi & Aleksandr Sav, 2022. "Red edge effect and chromoselective photocatalysis with amorphous covalent triazine-based frameworks," Nature Communications, Nature, vol. 13(1), pages 1-13, December.
    4. Guiyun Zhao & Wei Peng & Kaihui Song & Jingkun Shi & Xingyu Lu & Binju Wang & Yi-Ling Du, 2021. "Molecular basis of enzymatic nitrogen-nitrogen formation by a family of zinc-binding cupin enzymes," Nature Communications, Nature, vol. 12(1), pages 1-10, December.
    5. Zhijun Li & Xiaowen Lu & Cong Guo & Siqi Ji & Hongxue Liu & Chunmin Guo & Xue Lu & Chao Wang & Wensheng Yan & Bingyu Liu & Wei Wu & J. Hugh Horton & Shixuan Xin & Yu Wang, 2024. "Solvent-free selective hydrogenation of nitroaromatics to azoxy compounds over Co single atoms decorated on Nb2O5 nanomeshes," Nature Communications, Nature, vol. 15(1), pages 1-11, 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:15:y:2024:i:1:d:10.1038_s41467-024-52648-0. 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.