Ortho-boronoaldehydes react with amine-based nucleophiles with dramatically increased rates and product stabilities, relative to unfunctionalised benzaldehydes, leading to exciting applications across biological and material chemistry. We have developed a novel Förster resonance energy transfer (FRET)-based assay to provide key new insights into the reactivity of these boronoaldehydes, allowing us to track conjugation with unprecedented sensitivity and accuracy under standardised conditions. Our results highlight the key role played by reaction pH, buffer additives, and boronoaldehyde structure in controlling conjugation speed and stability, providing design criteria for further innovations and applications in the field.
Bibliographical note© 2022 The Author(s)
Prof. Dave Smith and Dr Will Unsworth are thanked for insightful discussions throughout this work. N. C. R. and C. D. S. acknowledge PhD Studentship support from the EPSRC Doctoral Training Partnership and the University of York. A. V. S. acknowledges support from the Erasmus++ Programme. E. F. T. is grateful to the Royal Society of Chemistry for funding an Undergraduate Research Bursary. DFT calculations were undertaken on the Viking Cluster, which is a high-performance computer facility provided by the University of York. We are grateful for computational support from the University of York High Performance Computing service, Viking and the Research Computing team. J. M. L. is supported through a Royal Society Industrial Fellowship (2022–24). C. D. S. acknowledges support from the Royal Society of Chemistry Research Fund (RF19-8128) and a Royal Society Research Grant (RGS\R1\19120).