Reversible click reactions with boronic acids to build supramolecular architectures in water.
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.
Department of Organic Chemistry III, University of Ulm, Albert-Einstein-Allee 11, 89081 Ulm (Germany), Fax: (+49) 7315022879.
Matthias
M
Arzt
Christiane
C
Seidler
David Y W
DY
Ng
Tanja
T
Weil
D001897:Boronic Acids / Q000737:chemistry*; D057930:Click Chemistry; D009682:Magnetic Resonance Spectroscopy; D013056:Spectrophotometry, Ultraviolet; D014867:Water / Q000737:chemistry*
D001897:Boronic Acids; D014867:Water
bioorthogonality; boronic acids; click reactions; pH-reversibility