Polysulfurating reagents designed for unsymmetrical polysulfide construction

2018-06-29


ON June 6, Prof. Jiang Xuefeng and his team members published their article Polysulfurating reagent design for unsymmetrical polysulfide construction in the peer-reviewed international academic journal Nature Communications.


Jiang Xuefeng

From life science to material science, to pharmaceutical industry, and to food chemistry, polysulfides are vital structural scaffolds. However, there are limited synthetic methods for unsymmetrical polysulfides. Conventional strategies entail two pre-sulfurated cross-coupling substrates, R–S, with higher chances of side reactions due to the characteristic of sulfur.

Herein, Prof. Jiang’s research team designed a library of broad-spectrum polysulfurating reagents, R–S–S–OMe, to which the R–S–S source can be directly introduced for late-stage modifications of biomolecules, natural products, and pharmaceuticals. Based on the hard and soft acids and bases principle, selective activation of sulfur-oxygen bond has been accomplished via utilizing proton and boride for efficient unsymmetrical polysulfuration. These polysulfurating reagents are highlighted with their outstanding multifunctional gram-scale transformations with various nucleophiles under mild conditions. 

Prof. Jiang and his team members

In Jiang and his team members’ experiments, a class of stable and broad-spectrum polysulfurating reagents with masked strategy has been designed and a general polysulfurating methodology has been established under mild conditions, which can directly introduce two sulfur atoms into functional molecules. The designed reagents were compatible with a considerable range of significant biomolecules, such as saccharides, amino acids, peptides and variety of heterocycles.

This protocol showcases the wide utility of both carbon and nitrogen nucleophiles resulting in the functional disulfides. Furthermore, the trisulfuration provides a convenient and efficient method for sulfur-containing drug discovery. Further studies on modification of biomolecules and pharmaceuticals with these disulfurating reagents are still ongoing.






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华东师范大学
East China Normal University