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Updated: Jan 5, 2026

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation
Published on: August 1, 2018
A Tripeptide Approach to the Solid-Phase Synthesis of Peptide Thioacids and N-Glycopeptides
Markus Julian Schöwe1, Odin Keiper1, Carlo Unverzagt2
1Department of Chemistry, University of Konstanz, 78457, Konstanz, Germany.
Abstract:
A general and robust method for the incorporation of aspartates with a thioacid side chain into peptides has been developed. Pseudoproline tripeptides served as building blocks for the efficient fluorenylmethyloxycarbonyl (Fmoc) solid-phase synthesis of thioacid-containing peptides. These peptides were readily converted to complex N-glycopeptides by using a fast and chemoselective one-pot deprotection/ligation procedure. Furthermore, a novel side reaction that can lead to site-selective peptide cleavage using thioacids (CUT) was discovered and studied in detail.
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