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Updated: Oct 11, 2025

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation
Published on: August 1, 2018
Ynamide-Mediated Thioester Synthesis
Xuewei Wang1, Yongli Zhao1, Jinhua Yang2
1College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, P. R. China.
Abstract:
A novel ynamide-mediated thioester synthesis strategy was developed. Importantly, no detectable racemization was observed for the thioesterifications of carboxylic acids containing an α-chiral center, enabling it to be useful for the synthesis of peptide thioester, which is the key component of native chemical ligation. It is worth mentioning that amino acid side chain functional groups such as -OH and indole -NH are compatible with the reaction conditions, rendering their protection unnecessary. Moreover, this method was also amenable to selenoesters.
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