Journal of the American Chemical Society· 2026Q1
Traceless Peptide Backbone Editing via Bioinspired Cysteine-to-Thiazole Conversion
- 1citations
- Q1SCImago
- 2026year
Short summary
A new bioinspired method enables traceless editing of peptide backbones by converting cysteine residues into thiazoles using a label-and-edit strategy.
AI-generated from the title and abstract; the full text is not read.
Key points
- Developed a "label-and-edit" strategy for peptide backbone modification.
- Bioinspired by natural cysteine-to-thiazole conversion.
- Involves selective labeling of cysteine thiols with 2-bromoacetophenone.
- Photoinduced cyclization generates thiazole-containing peptides.
- Transformation is traceless and compatible with diverse peptides.
AI-generated from the title and abstract; the full text is not read.
Abstract
Abstract Late-stage peptide modification is a powerful strategy for diversifying and expanding peptide bioactivity. Although numerous methods have been developed for peptide side-chain functionalization, chemical approaches for selective backbone editing remain scarce. Inspired by the natural enzyme-mediated conversion of cysteine residues into thiazoles during peptide biosynthesis, we developed a traceless “label-and-edit” strategy for the backbone modification of cysteine-containing peptides. This approach begins with the selective labeling of cysteine thiols using 2-bromoacetophenone, followed by photoinduced generation of a thioaldehyde/enethiol intermediate and subsequent intramolecular SH/amide cyclization to afford thiazole-containing peptides. The transformation is compatible with a broad range of synthetic and natural peptides, highlighting its potential as a versatile platform for late-stage peptide backbone editing and diversification.
The authors' abstract, as published at the source. Journal of the American Chemical Society, 2026 · DOI ↗
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Field: Organic Chemistry
Organic ChemistryChemistry