Dimethyl sulfate and diisopropyl sulfate as practical and versatile O-sulfation reagents
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 forma...
| Main Authors: | , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Nature Portfolio
2024-02-01
|
| Series: | Nature Communications |
| Online Access: | https://doi.org/10.1038/s41467-024-46214-x |
| _version_ | 1827326989568049152 |
|---|---|
| author | Shuaishuai Yue Guoping Ding Ye Zheng Chunlan Song Peng Xu Biao Yu Jiakun Li |
| author_facet | Shuaishuai Yue Guoping Ding Ye Zheng Chunlan Song Peng Xu Biao Yu Jiakun Li |
| author_sort | Shuaishuai Yue |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-03-07T14:53:27Z |
| format | Article |
| id | doaj.art-607e3dba9af04516b10570bda86039a6 |
| institution | Directory Open Access Journal |
| issn | 2041-1723 |
| language | English |
| last_indexed | 2024-03-07T14:53:27Z |
| publishDate | 2024-02-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Nature Communications |
| spelling | doaj.art-607e3dba9af04516b10570bda86039a62024-03-05T19:32:19ZengNature PortfolioNature Communications2041-17232024-02-011511710.1038/s41467-024-46214-xDimethyl sulfate and diisopropyl sulfate as practical and versatile O-sulfation reagentsShuaishuai Yue0Guoping Ding1Ye Zheng2Chunlan Song3Peng Xu4Biao Yu5Jiakun Li6State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan UniversityState Key Laboratory of Chemical Biology, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling RoadState Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan UniversityState Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan UniversityState Key Laboratory of Chemical Biology, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling RoadState Key Laboratory of Chemical Biology, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling RoadState Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan UniversityAbstract 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.https://doi.org/10.1038/s41467-024-46214-x |
| spellingShingle | Shuaishuai Yue Guoping Ding Ye Zheng Chunlan Song Peng Xu Biao Yu Jiakun Li Dimethyl sulfate and diisopropyl sulfate as practical and versatile O-sulfation reagents Nature Communications |
| title | Dimethyl sulfate and diisopropyl sulfate as practical and versatile O-sulfation reagents |
| title_full | Dimethyl sulfate and diisopropyl sulfate as practical and versatile O-sulfation reagents |
| title_fullStr | Dimethyl sulfate and diisopropyl sulfate as practical and versatile O-sulfation reagents |
| title_full_unstemmed | Dimethyl sulfate and diisopropyl sulfate as practical and versatile O-sulfation reagents |
| title_short | Dimethyl sulfate and diisopropyl sulfate as practical and versatile O-sulfation reagents |
| title_sort | dimethyl sulfate and diisopropyl sulfate as practical and versatile o sulfation reagents |
| url | https://doi.org/10.1038/s41467-024-46214-x |
| work_keys_str_mv | AT shuaishuaiyue dimethylsulfateanddiisopropylsulfateaspracticalandversatileosulfationreagents AT guopingding dimethylsulfateanddiisopropylsulfateaspracticalandversatileosulfationreagents AT yezheng dimethylsulfateanddiisopropylsulfateaspracticalandversatileosulfationreagents AT chunlansong dimethylsulfateanddiisopropylsulfateaspracticalandversatileosulfationreagents AT pengxu dimethylsulfateanddiisopropylsulfateaspracticalandversatileosulfationreagents AT biaoyu dimethylsulfateanddiisopropylsulfateaspracticalandversatileosulfationreagents AT jiakunli dimethylsulfateanddiisopropylsulfateaspracticalandversatileosulfationreagents |