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Issue 6, 2015
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Boronic acids facilitate rapid oxime condensations at neutral pH

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Abstract

We report here the discovery and development of boron-assisted oxime formation as a powerful connective reaction for chemical biology. Oximes proximal to boronic acids form in neutral aqueous buffer with rate constants of more than 104 M−1 s−1, the largest to date for any oxime condensation. Boron's dynamic coordination chemistry confers an adaptability that seems to aid a number of elementary steps in the oxime condensation. In addition to applications in bioconjugation, the emerging importance of boronic acids in chemical biology as carbohydrate receptors or peroxide probes, and the growing list of drugs and drug candidates containing boronic acids suggest many potential applications.

Graphical abstract: Boronic acids facilitate rapid oxime condensations at neutral pH

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Supplementary files

Article information


Submitted
13 Mar 2015
Accepted
07 Apr 2015
First published
13 Apr 2015

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2015,6, 3329-3333
Article type
Edge Article

Boronic acids facilitate rapid oxime condensations at neutral pH

P. Schmidt, C. Stress and D. Gillingham, Chem. Sci., 2015, 6, 3329 DOI: 10.1039/C5SC00921A

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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