Journal
ORGANIC LETTERS
Volume 24, Issue 2, Pages 581-586Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c04017
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Funding
- National Key Research and Development Program Synthetic Biology Key Special Project of China [2018YFA0902504]
- Natural Science Foundation of China [21778009, 21977010]
- Natural Science Foundation of Guangdong Province [2020 A1515010766, 2020 A1515010522, 2019A1515111184]
- Shenzhen Science and Technology Innovation Committee [RCJC20200714114433053, JCYJ20180507181659781, JCYJ201805081522131455, JCYJ20200109140406047]
- Beijing National Laboratory of Molecular Science [BNLMS20160112]
- Shenzhen-Hong Kong Institute of Brain Science-Shenzhen Fundamental Research Institutions [2019SHIBS0004]
- Proteomic Platform of Pingshan Translational Medicine Center, Shenzhen Bay Laboratory
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A novel amidation strategy using electrophilic sulfonium has been developed, enabling efficient amidation reactions in aqueous environments and solid-phase peptide synthesis. It also finds applications in peptide/protein modifications and activity-based protein profiling of a proteome at pH 10. Additionally, this method was used for peptide ligand-directed labeling of the USP7-UBL2 domain.
A novel amidation strategy using electrophilic sulfonium, which is soluble and stable in aqueous conditions, was developed. The sulfoniums could activate thioacid and carboxyl acid to efficiently react with amines to afford amides. This method enables applications in amidation in both aqueous media and solid-phase peptide synthesis, peptide/protein modifications, and reactive lysines of a proteome at pH 10 with activity-based protein profiling. A peptide ligand-directed labeling of the USP7-UBL2 domain was also performed using this method.
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