Molecular recognition with boronic acids—applications in chemical biology

Abstract

Small molecules have long been used for the selective recognition of a wide range of analytes. The ability of these chemical receptors to recognise and bind to specific targets mimics certain biological processes (such as proteinsubstrate interactions) and has therefore attracted recent interest. Due to the abundance of biological molecules possessing polyhydroxy motifs, boronic acids-which form fivemembered boronate esters with diols-have become increasingly popular in the synthesis of small chemical receptors. Their targets include biological materials and natural products including phosphatidylinositol bisphosphate, saccharides and polysaccharides, nucleic acids, metal ions and the neurotransmitter dopamine. This review will focus on the many ways in which small chemical receptors based on boronic acids have been used as biochemical tools for various purposes, including sensing and detection of analytes, interference in signalling pathways, enzyme inhibition and cell delivery systems. The most recent developments in each area will be highlighted.

Chemical intervention tools to probe phosphoinositide-dependent signalling

“…This will result in a local rearrangement of the lipids in the membrane, generating a much wider distance between the individual lipids (blue arrows). In contrast, the much smaller chemical mimetic PHDM (shown in green) will bind two headgroups [36], but occupies a much smaller space.…”

Cross‐Linking Building Blocks Using a “Boronate Bridge” to Build Functional Hybrid Materials

“…Another important aspect of BAs is their unique molecular recognition properties, which are used in the field of supramolecular chemistry. BAs form reversible covalent bonds with compounds possessing functional groups containing heteroatoms such as diols, amino acids, and hydroxamic acids . Especially, cyclic ester species formed by BAs and diols are called boronic esters or boronate esters (when in their anionic form), and these have been extensively studied .…”

Synthesis and Evaluation of the Anticancer and Trypanocidal Activities of Boronic Tyrphostins

“…[1] Althought hey were first reported in 1860 by Frankland and Duppa, [2] boronic acids only gained notoriety after the development of the palladium-catalyzedS uzuki-Miyaura CÀCcoupling reaction. [3,4] Until recently,t he application of boronic acids in medicinal chemistry was very restricted to their uses as chemosensors [5] or as reagents for the synthesis of active molecules. [6] In 2003, however,b ortezomib ( Figure 1) was approved for the treatment of people affected by multiple myeloma( MM), at ype of blood cancerthat developsint he bone marrow.…”