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Updated: Mar 25, 2026

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
Published on: August 19, 2012
Fast and Tight Boronate Formation for Click Bioorthogonal Conjugation
1Department of Chemistry, 4-010 CCIS, University of Alberta, Edmonton, Alberta, T6G 2G2, Canada.
Abstract:
A new click bioorthogonal reaction system was devised to enable the fast ligation (k(ON) ≈340 m(-1) s(-1)) of conjugatable derivatives of a rigid cyclic diol (nopoldiol) and a carefully optimized boronic acid partner, 2-methyl-5-carboxymethylphenylboronic acid. Using NMR and fluorescence spectroscopy studies, the corresponding boronates were found to form reversibly within minutes at low micromolar concentration in water, providing submicromolar equilibrium constant (K(eq) ≈10(5) -10(6) m(-1)). Efficient protein conjugation under physiological conditions was demonstrated with model proteins thioredoxin and albumin, and characterized by mass spectrometry and gel electrophoresis.
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