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Updated: Sep 11, 2025

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
Published on: August 19, 2012
Construction of a Chiral Click Chemistry Platform via Enantioselective F/Cl Exchange at S(VI) Centers
Daming Zeng1, Xinyu Zhang1, Hanliang Zheng2
1Hainan Institute of East China Normal University, State Key Laboratory of Petroleum Molecular & Process Engineering, Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, China.
Abstract:
Sulfonimidoyl fluorides have emerged as versatile click linkers, where the construction of sulfur-centered chirality plays a pivotal role in chiral recognition, stereoselective binding, and spatial interactions. However, the enantioselective formation of S(VI)-F bonds faces a significant challenge due to facile racemization from low activation barriers. Herein, we introduce inorganic sodium bifluoride (NaHF2), which enables a three-dimensional hydrogen-bonding network to promote stereoinversion of the S-Cl bond via dynamic kinetic asymmetric fluorination, thereby delivering excellent yields and enantioselectivities. Mechanistic studies reveal that a robust hydrogen-bonding catalytic complex with the HF2- anion is essential for enantiocontrol. This strategy paves the way for chiral click bioconjugation.
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