Radical-mediated thiol-ene 'click' reactions in deep eutectic solvents for bioconjugation

Herein, we report the first application of deep eutectic solvents (DESs) in radical-mediated hydrothiolation reactions. Under UV and atmospheric-oxygen mediated conditions, the thiol-ene reaction was applied to amino acid and peptide ligation in DESs. The conditions facilitate highly-efficient synth...

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Bibliographic Details
Published inGreen chemistry : an international journal and green chemistry resource : GC Vol. 24; no. 4; pp. 1456 - 1462
Main Authors Nolan, Mark D, Mezzetta, Andrea, Guazzelli, Lorenzo, Scanlan, Eoin M
Format Journal Article
LanguageEnglish
Published Cambridge Royal Society of Chemistry 21.02.2022
Subjects
ACE2
Amino acids
Angiotensin
Angiotensin-converting enzyme 2
COVID-19
Eutectic reactions
Fluorescence
Glycosylation
Green chemistry
Infectivity
Labeling
Peptidyl-dipeptidase A
Severe acute respiratory syndrome coronavirus 2
Solvents
Spike protein
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Summary:Herein, we report the first application of deep eutectic solvents (DESs) in radical-mediated hydrothiolation reactions. Under UV and atmospheric-oxygen mediated conditions, the thiol-ene reaction was applied to amino acid and peptide ligation in DESs. The conditions facilitate highly-efficient synthesis of biomolecular targets using a 'green' methodology, with complete recycling of the reaction medium. Fluorescent labelling and glycosylation of a minimal sequence mimetic of angiotensin-converting enzyme 2 capable of binding the SARS-CoV-2 spike protein is demonstrated for applications in the study of inhibition of COVID-19 infectivity. Herein, we report the first application of deep eutectic solvents (DESs) in radical-mediated hydrothiolation reactions.
Bibliography:10.1039/d1gc03714e
Electronic supplementary information (ESI) available. See DOI
ISSN:1463-9262
1463-9270
DOI:10.1039/d1gc03714e