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Molecular mechanism of azoxy bond formation for azoxymycins biosynthesis

Author

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  • Yuan-Yang Guo

    (Zhejiang University School of Medicine
    Henan Normal University)

  • Zhen-Hua Li

    (Zhejiang University School of Medicine)

  • Tian-Yu Xia

    (Zhejiang University School of Medicine)

  • Yi-Ling Du

    (Zhejiang University School of Medicine)

  • Xu-Ming Mao

    (Zhejiang University School of Medicine)

  • Yong-Quan Li

    (Zhejiang University School of Medicine)

Abstract

Azoxy bond is an important chemical bond and plays a crucial role in high energy density materials. However, the biosynthetic mechanism of azoxy bond remains enigmatic. Here we report that the azoxy bond biosynthesis of azoxymycins is an enzymatic and non-enzymatic coupling cascade reaction. In the first step, nonheme diiron N-oxygenase AzoC catalyzes the oxidization of amine to its nitroso analogue. Redox coenzyme pairs then facilitate the mutual conversion between nitroso group and hydroxylamine via the radical transient intermediates, which efficiently dimerize to azoxy bond. The deficiency of nucleophilic reactivity in AzoC is proposed to account for the enzyme’s non-canonical oxidization of amine to nitroso product. Free nitrogen radicals induced by coenzyme pairs are proposed to be responsible for the efficient non-enzymatic azoxy bond formation. This mechanism study will provide molecular basis for the biosynthesis of azoxy high energy density materials and other valuable azoxy chemicals.

Suggested Citation

  • 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.
    • Handle: RePEc:nat:natcom:v:10:y:2019:i:1:d:10.1038_s41467-019-12250-1
    DOI: 10.1038/s41467-019-12250-1
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    Cited by:

    1. 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.
    2. 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.

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