A thiol-ene mediated approach for peptide bioconjugation using 'green' solvents under continuous flow

Flow chemistry has emerged as an integral process within the chemical sector permitting energy efficient synthetic scale-up while improving safety and minimising solvent usage. Herein, we report the first applications of the photoactivated, radical-mediated thiol-ene reaction for peptide bioconjugat...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2024-03, Vol.22 (11), p.223-221
Main Authors: Rabadán González, Inés, McLean, Joshua T, Ostrovitsa, Nikita, Fitzgerald, Sheila, Mezzetta, Andrea, Guazzelli, Lorenzo, O'Shea, Donal F, Scanlan, Eoin M
Format: Article
Language:English
Subjects:
Chemical reactions
Continuous flow
Energy efficiency
Eutectic reactions
Organic solvents
Peptides
Photoinitiators
Solvents
Substrates
Sulfhydryl Compounds
Water
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Summary:Flow chemistry has emerged as an integral process within the chemical sector permitting energy efficient synthetic scale-up while improving safety and minimising solvent usage. Herein, we report the first applications of the photoactivated, radical-mediated thiol-ene reaction for peptide bioconjugation under continuous flow. Bioconjugation reactions employing deep eutectic solvents, bio-based solvents and fully aqueous systems are reported here for a range of biologically relevant peptide substrates. The use of a water soluble photoinitiator, Irgacure 2959, permitted synthesis of glycosylated peptides in fully aqueous conditions, obviating the need for addition of organic solvents and enhancing the green credentials of these rapid, photoactivated, bioconjugation reactions. The photochemical thiol-ene reaction employing green solvents under continuous-flow conditions is reported as a versatile method for peptide bioconjugation.
ISSN:1477-0520
1477-0539
DOI:10.1039/d4ob00122b