Issue 15, 2020

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

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

Supplementary files

Article information

Article type
Communication
Submitted
03 Oct 2019
Accepted
24 Mar 2020
First published
25 Mar 2020

Org. Biomol. Chem., 2020,18, 2823-2827

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

S. Kanai, K. Machida, R. Masuda and T. Koide, Org. Biomol. Chem., 2020, 18, 2823 DOI: 10.1039/C9OB02136A

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