Journal
CHEMICAL COMMUNICATIONS
Volume 51, Issue 95, Pages 16992-16995Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c5cc07453c
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Funding
- NIH [R15 GM-093941]
- Harpur College Dean's Office, Binghamton University
- NSF [CHE-0922815]
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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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