Peptide precursors that acquire denatured collagen-hybridizing ability by O-to-N acyl migration at physiological pH.
Sayaka KanaiKoshi MachidaRyo MasudaTakaki KoidePublished in: Organic & biomolecular chemistry (2020)
Here, we report peptide probes with either single or cyclic double stranded collagen-like sequences that spontaneously acquire collagen-hybridizing ability at physiological pH. These peptides have ester bonds derived from O-acyl isopeptide units that are converted to amide bonds via intramolecular O-to-N acyl migration by a pH shift. The peptides that do not require pre-treatment for disassembly will be useful as prodrugs in theranostic treatments targeting unfolded collagen.