Structure-guided design and photochemical synthesis of new carbamo(dithioperoxo)thioates with improved potencies to SARS-CoV-2 3CLpro

Yin, De-Hang; Xin, Jie; Chen, Shizhao; Li, Shuai-Shuai; Li, Zi-Ying; Meng, Jin-Xi; Lin, Yue-Chi; Yin, Bing-Qian; Zhao, Cheng; Li, Jia; Gao, Hang; Tian, Jun; Gao, Wen-Chao

doi:10.1016/j.bmc.2024.117940

Bioorganic & Medicinal Chemistry

2024

DOI: 10.1016/j.bmc.2024.117940

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Structure-guided design and photochemical synthesis of new carbamo(dithioperoxo)thioates with improved potencies to SARS-CoV-2 3CLpro

De-Hang Yin,

Jie Xin,

Shizhao Chen

et al.

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Synthesis of Unsymmetrical Disulfides via Photocatalytic Hydrodisulfuration

Dong,

Wang,

Zhang

et al. 2024

ACS Catal.

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Photoredox catalysis is an appealing strategy for the C−S bond formation. Herein, we disclose the photocatalytic reductive hydrodisulfuration of electron-deficient alkenes for the synthesis of unsymmetrical disulfides. Mechanistic studies indicate that while the radical initiation occurs in this reaction, the perthiolate anion generated from the reduction of tetrasulfides via single-electron transfer is the key electron donor for the conjugate addition. This methodology exhibits broad functional group tolerance and allows the late-stage installation of disulfide motifs into marketed drugs and the preparation of peptides containing the disulfide bond under cysteine-free conditions. Moreover, the mechanism of ionic addition is further explained by control experiments and computations.

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Synthesis of Unsymmetrical Disulfides via Photocatalytic Hydrodisulfuration

Dong,

Wang,

Zhang

et al. 2024

ACS Catal.

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show abstract

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Structure-guided design and photochemical synthesis of new carbamo(dithioperoxo)thioates with improved potencies to SARS-CoV-2 3CLpro

Cited by 1 publication

References 26 publications

Synthesis of Unsymmetrical Disulfides via Photocatalytic Hydrodisulfuration

Synthesis of Unsymmetrical Disulfides via Photocatalytic Hydrodisulfuration

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