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

Shuaishuai Yue, Guoping Ding, Ye Zheng, Chunlan Song (), Peng Xu (), Biao Yu and Jiakun Li ()
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Shuaishuai Yue: College of Chemistry and Chemical Engineering, Hunan University
Guoping Ding: Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road
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

Nature Communications, 2024, vol. 15, issue 1, 1-7

Abstract: 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.

Date: 2024
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DOI: 10.1038/s41467-024-46214-x

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