Reversible click reactions with boronic acids to build supramolecular architectures in water

Matthias Arzt; Christiane Seidler; David Y W Ng; Tanja Weil

doi:10.1002/asia.201402061

Reversible click reactions with boronic acids to build supramolecular architectures in water

Chem Asian J. 2014 Aug;9(8):1994-2003. doi: 10.1002/asia.201402061. Epub 2014 Apr 24.

Authors

Matthias Arzt¹, Christiane Seidler, David Y W Ng, Tanja Weil

Affiliation

¹ Department of Organic Chemistry III, University of Ulm, Albert-Einstein-Allee 11, 89081 Ulm (Germany), Fax: (+49) 7315022879.

PMID: 24764166
DOI: 10.1002/asia.201402061

Abstract

The interaction of boronic acids with various bifunctional reagents offers great potential for the preparation of responsive supramolecular architectures. Boronic acids react with 1,2-diols yielding cyclic boronate esters that are stable at pH>7.4 but can be hydrolyzed at pH<5.0. The phenylboronic acid (PBA)-salicylhydroxamic acid (SHA) system offers ultra-fast reaction kinetics and high binding affinities. This Focus Review summarizes the current advances in exploiting the bioorthogonal interaction of boronic acids to build pH-responsive supramolecular architectures in water.

Keywords: bioorthogonality; boronic acids; click reactions; pH-reversibility.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Boronic Acids / chemistry*
Click Chemistry*
Magnetic Resonance Spectroscopy
Spectrophotometry, Ultraviolet
Water / chemistry*

Substances

Boronic Acids
Water