Abstract
Structure–activity relationship studies are a highly time-consuming aspect of peptide-based drug development, particularly in the assembly of disulfide-rich peptides, which often requires multiple synthetic steps and purifications. Therefore, it is vital to develop rapid and efficient chemical methods to readily access the desired peptides. We have developed a photolysis-mediated “one-pot” strategy for regioselective disulfide bond formation. The new pairing system utilises two ortho-nitroveratryl protected cysteines to generate two disulfide bridges in less than one hour in good yield. This strategy was applied to the synthesis of complex disulfide-rich peptides such as Rho-conotoxin ρ-TIA and native human insulin.
Original language | English |
---|---|
Pages (from-to) | 8599-8603 |
Number of pages | 5 |
Journal | Chemistry - A European Journal |
Volume | 25 |
Issue number | 36 |
DOIs | |
Publication status | Published - 26 Jun 2019 |
Keywords
- disulfides
- peptides
- photolysis
- protein engineering
- protein folding
- structure–activity relationships