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- Title
Fast and Tight Boronate Formation for Click Bioorthogonal Conjugation.
- Authors
Akgun, Burcin; Hall, Dennis G.
- Abstract
A new click bioorthogonal reaction system was devised to enable the fast ligation ( kON≈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 ( Keq≈105-106 m−1). Efficient protein conjugation under physiological conditions was demonstrated with model proteins thioredoxin and albumin, and characterized by mass spectrometry and gel electrophoresis.
- Subjects
BORONIC acids; ORGANIC compounds; BIOCONJUGATES; BIOMOLECULES; MASS spectrometers
- Publication
Angewandte Chemie, 2016, Vol 128, Issue 12, p3977
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201510321