Carbon dioxide enhances sulphur-selective conjugate addition reactions
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Carbon dioxide enhances sulphur-selective conjugate addition reactions. / Yang, Yang; Fischer, Niklas Henrik; Oliveira, Maria Teresa; Hadaf, Gul Barg; Liu, Jian; Brock-nannestad, Theis; Diness, Frederik; Lee, Ji-woong.
In: Organic & Biomolecular Chemistry, Vol. 20, No. 22, 2022, p. 4526–4533.Research output: Contribution to journal › Journal article › Research › peer-review
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TY - JOUR
T1 - Carbon dioxide enhances sulphur-selective conjugate addition reactions
AU - Yang, Yang
AU - Fischer, Niklas Henrik
AU - Oliveira, Maria Teresa
AU - Hadaf, Gul Barg
AU - Liu, Jian
AU - Brock-nannestad, Theis
AU - Diness, Frederik
AU - Lee, Ji-woong
PY - 2022
Y1 - 2022
N2 - 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.
AB - 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.
U2 - 10.1039/D2OB00831A
DO - 10.1039/D2OB00831A
M3 - Journal article
VL - 20
SP - 4526
EP - 4533
JO - Organic & Biomolecular Chemistry
JF - Organic & Biomolecular Chemistry
SN - 1470-4358
IS - 22
ER -
ID: 308489402