title: Fast and Tight Boronate Formation for Click Bioorthogonal Conjugation.
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.
authors.affiliation: Department of Chemistry, 4-010 CCIS, University of Alberta, Edmonton, Alberta, T6G 2G2, Canada.
authors.forename: Burcin
authors.initials: B
authors.lastname: Akgun
authors.affiliation: Department of Chemistry, 4-010 CCIS, University of Alberta, Edmonton, Alberta, T6G 2G2, Canada. dennis.hall@ualberta.ca.
authors.forename: Dennis G
authors.identifier: http://orcid.org/0000-0001-8555-6400
authors.initials: DG
authors.lastname: Hall
mesh_terms: D001897:Boronic Acids / Q000737:chemistry*; D057930:Click Chemistry; D009682:Magnetic Resonance Spectroscopy; D013050:Spectrometry, Fluorescence
chemical_list: D001897:Boronic Acids
keywords: bioorthogonality; boronates; boronic acids; click chemistry; protein labeling