Issue 22, 2022

Carbon dioxide enhances sulphur-selective conjugate addition reactions

Abstract

Sulphur-selective conjugate addition reactions play a central role in synthetic chemistry and chemical biology. A general tool for conjugate addition reactions should provide high selectivity in the presence of competing nucleophilic functional groups, namely nitrogen nucleophiles. We report CO2-mediated chemoselective S-Michael addition reactions where CO2 can reversibly control the reaction pHs, thus providing practical reaction conditions. The increased chemoselectivity for sulphur-alkylation products was ascribed to CO2 as a temporary and traceless protecting group for nitrogen nucleophiles, while CO2 efficiently provide higher conversion and selectivity sulphur nucleophiles on peptides and human serum albumin (HSA) with various electrophiles. This method offers simple reaction conditions for cysteine modification reactions when high chemoselectivity is required.

Graphical abstract: Carbon dioxide enhances sulphur-selective conjugate addition reactions

Supplementary files

Article information

Article type
Communication
Submitted
02 May 2022
Accepted
18 May 2022
First published
18 May 2022

Org. Biomol. Chem., 2022,20, 4526-4533

Carbon dioxide enhances sulphur-selective conjugate addition reactions

Y. Yang, N. H. Fischer, M. T. Oliveira, G. B. Hadaf, J. Liu, T. Brock-Nannestad, F. Diness and J. Lee, Org. Biomol. Chem., 2022, 20, 4526 DOI: 10.1039/D2OB00831A

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