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Updated: Jan 14, 2026

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
Published on: September 28, 2022
Self-Assembly of Macrocyclic Hosts with Kinetic Inertness
Tayba Chudhary1, Yuxi Wei1, Lu Tong1
1Stoddart Institute of Molecular Science Department of Chemistry Zhejiang University, Hangzhou 310058, China.
Abstract:
A dynamic covalent reaction, namely, oxime condensation, was employed here to synthesize macrocycles, using strong acid to catalyze oxime exchange. When formyl precursors with lower water solubility were used, condensation reaction proceeded in a heterogeneous manner. In this case, slow addition of the acid catalyst was crucial to avoid rapid polymerization. These hosts become kinetically inert upon acid removal, which turns OFF the dynamic nature of the oxime bond. Moreover, the macrocycles with relatively larger π-electron hydrophobic building blocks are able to accommodate guests via hydrophobic effect.
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