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Dimethyl sulfate and diisopropyl sulfate as practical and versatile O-sulfation reagents

Author

Listed:
  • Shuaishuai Yue

    (College of Chemistry and Chemical Engineering, Hunan University)

  • Guoping Ding

    (Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road
    School of Pharmaceutical Engineering, Shenyang Pharmaceutical University)

  • Ye Zheng

    (College of Chemistry and Chemical Engineering, Hunan University)

  • Chunlan Song

    (College of Chemistry and Chemical Engineering, Hunan University)

  • Peng Xu

    (Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road)

  • Biao Yu

    (Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road)

  • Jiakun Li

    (College of Chemistry and Chemical Engineering, Hunan University)

Abstract

O-Sulfation is a vital post-translational modification in bioactive molecules, yet there are significant challenges with their synthesis. Dialkyl sulfates, such as dimethyl sulfate and diisopropyl sulfate are commonly used as alkylation agents in alkaline conditions, and result in the formation of sulfate byproducts. We report herein a general and robust approach to O-sulfation by harnessing the tunable reactivity of dimethyl sulfate or diisopropyl sulfate under tetrabutylammonium bisulfate activation. The versatility of this O-sulfation protocol is interrogated with a diverse range of alcohols, phenols and N-OH compounds, including carbohydrates, amino acids and natural products. The enhanced electrophilicity of the sulfur atom in dialkyl sulfates, facilitated by the interaction with bisulfate anion (HSO4-), accounts for this pioneering chemical reactivity. We envision that our method will be useful for application in the comprehension of biological functions and discovery of drugs.

Suggested Citation

  • Shuaishuai Yue & Guoping Ding & Ye Zheng & Chunlan Song & Peng Xu & Biao Yu & Jiakun Li, 2024. "Dimethyl sulfate and diisopropyl sulfate as practical and versatile O-sulfation reagents," Nature Communications, Nature, vol. 15(1), pages 1-7, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-46214-x
    DOI: 10.1038/s41467-024-46214-x
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