Insight into ortho-boronoaldehyde conjugation via a FRET-based reporter assay

Abstract

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.

Metadata

Item Type:	Article
Authors/Creators:	Rose, Nicholas C. Sanchez, Anaïs V. Tipple, Eve F. Lynam, Jason M. https://orcid.org/0000-0003-0103-9479 Spicer, Christopher D. https://orcid.org/0000-0001-8787-578X
Copyright, Publisher and Additional Information:	© 2022 The Author(s) Funding Information: 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).
Dates:	Published: 14 October 2022 Accepted: 13 October 2022
Institution:	The University of York
Academic Units:	The University of York > Faculty of Sciences (York) > Chemistry (York)
Depositing User:	Pure (York)
Date Deposited:	25 Nov 2022 09:40
Last Modified:	05 Jan 2025 00:36
Published Version:	https://doi.org/10.1039/d2sc04574e
Status:	Published
Refereed:	Yes
Identification Number:	10.1039/d2sc04574e
Related URLs:	http://www.scopus.com/inward/record.url?...
Open Archives Initiative ID (OAI ID):	oai:eprints.whiterose.ac.uk:193765

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Insight into ortho-boronoaldehyde conjugation via a FRET-based reporter assay

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