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Updated: Mar 23, 2026

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
Published on: August 19, 2012
Chemoselective Sequential Click Ligations Directed by Enhanced Reactivity of an Aromatic Ynamine
Marine Z C Hatit1, Joanna C Sadler1,2, Liam A McLean1
1Department of Pure and Applied Chemistry, WestCHEM, University of Strathclyde , Glasgow, G1 1XL, U.K.
Abstract:
Aromatic ynamines or N-alkynylheteroarenes are highly reactive alkyne components in Cu-catalyzed Huisgen [3 + 2] cycloaddition ("click") reactions. This enhanced reactivity enables the chemoselective formation of 1,4-triazoles using the representative aromatic ynamine N-ethynylbenzimidazole in the presence of a competing aliphatic alkyne substrate. The unique chemoselectivity profile of N-ethynylbenzimidazole is further demonstrated by the sequential click ligation of a series of highly functionalized azides using a heterobifunctional diyne, dispelling the need for alkyne protecting groups.
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