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Rapid formation of a stable boron-nitrogen heterocycle in dilute, neutral aqueous solution for bioorthogonal coupling
Ozlem Dilek1, Zhen Lei2, Kamalika Mukherjee2
1Department of Medical Biochemistry, School of Medicine, Istanbul Kemerburgaz University, Bagcilar, Istanbul 34217, Turkey. ozlem.dilek@kemerburgaz.edu.
Abstract:
Combining 2-formylphenylboronic acid with 4-hydrazinylbenzoic acid in neutral aqueous solution at low, equimolar concentrations of the reagents results in a single, stable product, a 1,2-dihydro-1-hydroxy-2,3,1-benzodiazaborine, in a matter of minutes with no side products. Application of this reaction to protein conjugation demonstrates that the reaction is orthogonal to protein functional groups, and the resulting conjugate withstands SDS-PAGE analysis. This reaction should be particularly useful for couplings that must be performed with low concentrations of reagents under physiologically compatible conditions.
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