Abstract
The thiol-ene ‘click’ reaction has emerged as a versatile process for carbon–sulfur bond formation with widespread applications in chemical biology, medicinal chemistry and materials science. Thioesters are key intermediates in a wide range of synthetic and biological processes and efficient methods for their synthesis are of considerable interest. Herein, we report the first examples of acyl-thiol-ene (ATE) for the synthesis of biomolecular thioesters, including peptide, lipid and carbohydrate derivatives. A key finding is the profound effect of the amino acid side chain on the outcome of the ATE reaction. Furthermore, radical generated thioesters underwent efficient S-to-N acyl transfer and desulfurisation to furnish ‘sulfur-free’ ligation products in an overall amidation process with diverse applications for chemical ligation and bioconjugation.
Original language | English |
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Pages (from-to) | 4148-4160 |
Number of pages | 13 |
Journal | European Journal of Organic Chemistry |
Volume | 2021 |
Issue number | 29 |
Early online date | 26 Jul 2021 |
DOIs | |
Publication status | Published - 6 Aug 2021 |
Keywords
- Amides
- Click Chemistry
- Hydrothiolation
- Radical Reactions
- Thiol-ene
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry