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SO2F2 mediated click chemistry enables modular disulfide formation in diverse reaction media

Author

Listed:
  • Hengzhao Li

    (China Agricultural University
    Northwest A&F University
    Food Laboratory of Zhongyuan)

  • Mengqi Peng

    (China Agricultural University)

  • Junyu Li

    (China Agricultural University)

  • Lijun Wang

    (China Agricultural University)

  • Hainam Do

    (University of Nottingham Ningbo China)

  • Ke Ni

    (China Agricultural University)

  • Minlong Wang

    (China Agricultural University)

  • Zhankui Yuan

    (China Agricultural University)

  • Tianxiao Zhao

    (China Agricultural University)

  • Xiaohe Zhang

    (China Agricultural University)

  • Xiaoxu Zhang

    (China Agricultural University)

  • Zhaonong Hu

    (Northwest A&F University)

  • Fazheng Ren

    (China Agricultural University)

  • Jie An

    (China Agricultural University)

Abstract

The dynamic disulfide linkage plays a vital role in various biological processes as well as drugs and biomaterials. The conversion of thiols to their corresponding disulfides is a hallmark of sulfur chemistry, but notoriously difficult to control. Achieving optimal reactivity and selectivity continues to pose significant challenges. Here, we describe a click chemistry for disulfide formation from thiols in both batch and flow-mode using SO2F2, which display exceptional selectivity toward disulfide formation through an effective nucleophilic substitution cascade. This reaction’s unique characteristics satisfy the stringent click-criteria with its high thermodynamic driving force, straightforward conditions, wide scope, quantitative yields, exceptional chemoselectivity, and non-chromatographic purification process. The modular synthesis of symmetrical, unsymmetrical, cyclic and polydisulfides is demonstrated, along with the formation of disulfide cross-linked hydrogels.

Suggested Citation

  • Hengzhao Li & Mengqi Peng & Junyu Li & Lijun Wang & Hainam Do & Ke Ni & Minlong Wang & Zhankui Yuan & Tianxiao Zhao & Xiaohe Zhang & Xiaoxu Zhang & Zhaonong Hu & Fazheng Ren & Jie An, 2024. "SO2F2 mediated click chemistry enables modular disulfide formation in diverse reaction media," Nature Communications, Nature, vol. 15(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-52606-w
    DOI: 10.1038/s41467-024-52606-w
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    References listed on IDEAS

    as
    1. Jiahui Xue & Xuefeng Jiang, 2020. "Unsymmetrical polysulfidation via designed bilateral disulfurating reagents," Nature Communications, Nature, vol. 11(1), pages 1-8, December.
    2. Xiao Xiao & Jiahui Xue & Xuefeng Jiang, 2018. "Polysulfurating reagent design for unsymmetrical polysulfide construction," Nature Communications, Nature, vol. 9(1), pages 1-9, December.
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