Peptide precursors that acquire denatured collagen-hybridizing ability by O-to-N acyl migration at physiological pH?

Organic & Biomolecular Chemistry Pub Date: 2020-03-25 DOI: 10.1039/C9OB02136A

Abstract

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.

Graphical abstract: Peptide precursors that acquire denatured collagen-hybridizing ability by O-to-N acyl migration at physiological pH
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