Carbon dioxide enhances sulphur-selective conjugate addition reactions.

Autor:	Yang Y; Department of Chemistry, University of Copenhagen Universitetsparken 5, Copenhagen Ø, 2100, Denmark. jiwoong.lee@chem.ku.dk., Fischer NH; Department of Chemistry, University of Copenhagen Universitetsparken 5, Copenhagen Ø, 2100, Denmark. jiwoong.lee@chem.ku.dk.; Nanoscience Center, University of Copenhagen Universitetsparken 5, Copenhagen Ø, 2100, Denmark., Oliveira MT; Department of Chemistry, University of Copenhagen Universitetsparken 5, Copenhagen Ø, 2100, Denmark. jiwoong.lee@chem.ku.dk.; Nanoscience Center, University of Copenhagen Universitetsparken 5, Copenhagen Ø, 2100, Denmark., Hadaf GB; Department of Chemistry, University of Copenhagen Universitetsparken 5, Copenhagen Ø, 2100, Denmark. jiwoong.lee@chem.ku.dk., Liu J; Department of Chemistry, University of Copenhagen Universitetsparken 5, Copenhagen Ø, 2100, Denmark. jiwoong.lee@chem.ku.dk., Brock-Nannestad T; Department of Chemistry, University of Copenhagen Universitetsparken 5, Copenhagen Ø, 2100, Denmark. jiwoong.lee@chem.ku.dk., Diness F; Department of Chemistry, University of Copenhagen Universitetsparken 5, Copenhagen Ø, 2100, Denmark. jiwoong.lee@chem.ku.dk.; Nanoscience Center, University of Copenhagen Universitetsparken 5, Copenhagen Ø, 2100, Denmark., Lee JW; Department of Chemistry, University of Copenhagen Universitetsparken 5, Copenhagen Ø, 2100, Denmark. jiwoong.lee@chem.ku.dk.; Nanoscience Center, University of Copenhagen Universitetsparken 5, Copenhagen Ø, 2100, Denmark.
Jazyk:	angličtina
Zdroj:	Organic & biomolecular chemistry [Org Biomol Chem] 2022 Jun 08; Vol. 20 (22), pp. 4526-4533. Date of Electronic Publication: 2022 Jun 08.
DOI:	10.1039/d2ob00831a
Abstrakt:	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 CO 2 -mediated chemoselective S -Michael addition reactions where CO 2 can reversibly control the reaction pHs, thus providing practical reaction conditions. The increased chemoselectivity for sulphur-alkylation products was ascribed to CO 2 as a temporary and traceless protecting group for nitrogen nucleophiles, while CO 2 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.
Databáze:	MEDLINE
Externí odkaz:	Zobrazit plný text záznamu