Issue 5, 2021

Boronic acid based dynamic click chemistry: recent advances and emergent applications

Abstract

Recently, reversible click reactions have found numerous applications in chemical biology, supramolecular chemistry, and biomedical applications. Boronic acid (BA)-mediated cis-diol conjugation is one of the best-studied reactions among them. An excellent understanding of the chemical properties and biocompatibility of BA-based compounds has inspired the exploration of novel chemistries using boron to fuel emergent sciences. This topical review focuses on the recent progress of iminoboronate and salicylhydroxamic–boronate constituted reversible click chemistries in the past decade. We highlight the mechanism of reversible kinetics and its applications in chemical biology, medicinal chemistry, biomedical devices, and material chemistry. This article also emphasizes the fundamental reactivity of these two conjugate chemistries with assorted nucleophiles at variable pHs, which is of utmost importance to any stimuli-responsive biological and material chemistry explorations.

Graphical abstract: Boronic acid based dynamic click chemistry: recent advances and emergent applications

Article information

Article type
Minireview
Submitted
10 Sept. 2020
Accepted
27 Nov. 2020
First published
17 Dec. 2020
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2021,12, 1585-1599

Boronic acid based dynamic click chemistry: recent advances and emergent applications

S. Chatterjee, E. V. Anslyn and A. Bandyopadhyay, Chem. Sci., 2021, 12, 1585 DOI: 10.1039/D0SC05009A

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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