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

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 SO<sub>2</sub>F<sub>2</sub>, 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.

Authors

Institutions

Publication Details

Journal
Nature Communications
Published
2024-09-27
DOI
https://doi.org/10.1038/s41467-024-52606-w
Citations
10
Primary Topic
Click Chemistry and Applications
Type
article
Field-Weighted Citation Impact
2.50

Funders

Controls
|||
ALL TIME
JAN
FEB
MAR
APR
MAY
JUN
JUL
AUG
SEP
OCT
article

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

Hengzhao Li, Jie An, Hainam Do, Mengqi Peng et al.
10 citations
Nature Communications
Click Chemistry and Applications
2.50
article

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

Hengzhao Li, Jie An, Hainam Do, Mengqi Peng, Zhankui Yuan, Minlong Wang, Zhaonong Hu, Xiaoxu Zhang, Junyu Li, Xiaohe Zhang, Ke Ni, Lijun Wang, Tianxiao Zhao, Fazheng Ren
article en
10 citations

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 SO<sub>2</sub>F<sub>2</sub>, 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.

Nature CommunicationsVol. 15(1)
University of Nottingham Ningbo China (CN), Ministry of Education (SA), Luohe Medical College (CN), China Agricultural University (CN), Northwest A&F University (CN)
National Natural Science Foundation of China, Higher Education Discipline Innovation Project, National Key Research and Development Program of China
Openalex Percentile: Top 11%
Click Chemistry and Applications
2.50
DOIOpen Access PDFOpenAlex
AI Navigator

Ask Laika to Summarize, Analyze, and Connect papers live on the map.

Summarize Papers & Methodologies

Extract key findings, datasets, and comparative methods across publications.

Benchmark Rankings & Visual Analytics

Rank top research institutions, authors, funders, topics, and journals by Field-Weighted Citation Impact (FWCI) and paper volume with instant charts.

Connect Distant Disciplines

Bridge topological clusters on the map to find hidden collaborative intersections.