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A thiol-ene mediated approach for peptide bioconjugation using 'green' solvents under continuous flow
Inés Rabadán González1, Joshua T McLean1, Nikita Ostrovitsa1
1Trinity Biomedical Sciences Institute, Trinity College Dublin, 152-160 Pearse Street, Dublin 2, Ireland. eoin.scanlan@tcd.ie.
Organic & Biomolecular Chemistry
|February 28, 2024
Summary
This study introduces photoactivated, radical-mediated thiol-ene reactions in flow chemistry for efficient peptide bioconjugation. These green chemistry methods work in aqueous systems, reducing solvent use and improving safety for peptide synthesis.
Area of Science:
- Green Chemistry
- Organic Synthesis
- Bioconjugation Chemistry
Background:
- Flow chemistry offers energy efficiency, improved safety, and reduced solvent use for synthetic scale-up.
- Peptide bioconjugation is crucial for developing therapeutics and diagnostics.
- Traditional bioconjugation methods can be inefficient and require harsh conditions or organic solvents.
Purpose of the Study:
- To report the first application of photoactivated, radical-mediated thiol-ene reactions for peptide bioconjugation under continuous flow conditions.
- To explore the use of various green solvents, including deep eutectic solvents, bio-based solvents, and aqueous systems, for peptide bioconjugation.
- To demonstrate the synthesis of glycosylated peptides in fully aqueous conditions using a water-soluble photoinitiator.
Main Methods:
- Utilized continuous flow reactors for rapid and controlled reaction conditions.
- Employed photoactivated, radical-mediated thiol-ene click chemistry.
- Investigated bioconjugation in diverse solvent systems: deep eutectic solvents, bio-based solvents, and aqueous media.
- Used a water-soluble photoinitiator (Irgacure 2959) for aqueous phase reactions.
Main Results:
- Successfully performed peptide bioconjugation using photoactivated thiol-ene reactions in flow.
- Demonstrated efficient bioconjugation across various solvent systems, including fully aqueous conditions.
- Achieved synthesis of glycosylated peptides in water without organic co-solvents.
- Highlighted the rapid nature and green credentials of the developed method.
Conclusions:
- Photoactivated, radical-mediated thiol-ene reactions in flow chemistry represent a novel and efficient approach for peptide bioconjugation.
- The developed method offers a greener alternative to traditional bioconjugation techniques by minimizing solvent usage and enabling aqueous-based synthesis.
- This methodology holds significant promise for the scalable and sustainable production of peptides and glycoproteins.
