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Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
Published on: August 19, 2012
Reversible click reactions with boronic acids to build supramolecular architectures in water
Matthias Arzt1, Christiane Seidler, David Y W Ng
1Department of Organic Chemistry III, University of Ulm, Albert-Einstein-Allee 11, 89081 Ulm (Germany), Fax: (+49) 7315022879.
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.
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