Carbon dioxide enhances sulphur-selective conjugate addition reactions

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Standard

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.

I: Organic & Biomolecular Chemistry, Bind 20, Nr. 22, 2022, s. 4526–4533.

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt

Harvard

Yang, Y, Fischer, NH, Oliveira, MT, Hadaf, GB, Liu, J, Brock-nannestad, T, Diness, F & Lee, J 2022, 'Carbon dioxide enhances sulphur-selective conjugate addition reactions', Organic & Biomolecular Chemistry, bind 20, nr. 22, s. 4526–4533. https://doi.org/10.1039/D2OB00831A

APA

Yang, Y., Fischer, N. H., Oliveira, M. T., Hadaf, G. B., Liu, J., Brock-nannestad, T., Diness, F., & Lee, J. (2022). Carbon dioxide enhances sulphur-selective conjugate addition reactions. Organic & Biomolecular Chemistry, 20(22), 4526–4533. https://doi.org/10.1039/D2OB00831A

Vancouver

Yang Y, Fischer NH, Oliveira MT, Hadaf GB, Liu J, Brock-nannestad T o.a. Carbon dioxide enhances sulphur-selective conjugate addition reactions. Organic & Biomolecular Chemistry. 2022;20(22):4526–4533. https://doi.org/10.1039/D2OB00831A

Author

Yang, Yang ; Fischer, Niklas Henrik ; Oliveira, Maria Teresa ; Hadaf, Gul Barg ; Liu, Jian ; Brock-nannestad, Theis ; Diness, Frederik ; Lee, Ji-woong. / Carbon dioxide enhances sulphur-selective conjugate addition reactions. I: Organic & Biomolecular Chemistry. 2022 ; Bind 20, Nr. 22. s. 4526–4533.

Bibtex

@article{4b68e3f6405f4933b02720f6d27bb7a0,
title = "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.",
author = "Yang Yang and Fischer, {Niklas Henrik} and Oliveira, {Maria Teresa} and Hadaf, {Gul Barg} and Jian Liu and Theis Brock-nannestad and Frederik Diness and Ji-woong Lee",
year = "2022",
doi = "10.1039/D2OB00831A",
language = "English",
volume = "20",
pages = "4526–4533",
journal = "Organic & Biomolecular Chemistry",
issn = "1470-4358",
publisher = "Royal Society of Chemistry",
number = "22",

}

RIS

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