Summary
A boronic acid is an organic compound related to boric acid () in which one of the three hydroxyl groups () is replaced by an alkyl or aryl group (represented by R in the general formula ). As a compound containing a carbon–boron bond, members of this class thus belong to the larger class of organoboranes. Boronic acids act as Lewis acids. Their unique feature is that they are capable of forming reversible covalent complexes with sugars, amino acids, hydroxamic acids, etc. (molecules with vicinal, (1,2) or occasionally (1,3) substituted Lewis base donors (alcohol, amine, carboxylate)). The pKa of a boronic acid is ~9, but they can form tetrahedral boronate complexes with pKa ~7. They are occasionally used in the area of molecular recognition to bind to saccharides for fluorescent detection or selective transport of saccharides across membranes. Boronic acids are used extensively in organic chemistry as chemical building blocks and intermediates predominantly in the Suzuki coupling. A key concept in its chemistry is transmetallation of its organic residue to a transition metal. The compound bortezomib with a boronic acid group is a drug used in chemotherapy. The boron atom in this molecule is a key substructure because through it certain proteasomes are blocked that would otherwise degrade proteins. Boronic acids are known to bind to active site serines and are part of inhibitors for porcine pancreatic lipase, subtilisin and the protease Kex2. Furthermore, boronic acid derivatives constitute a class of inhibitors for human acyl-protein thioesterase 1 and 2, which are cancer drug targets within the Ras cycle. The boronic acid functional group is reputed to have low inherent toxicity. This is one of the reasons for the popularity of the Suzuki coupling in the development and synthesis of pharmaceutical agents. However, a significant fraction of commonly used boronic acids and their derivatives were recently found to gives a positive Ames test and act as chemical mutagens.
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Related publications (5)

Half-clathrochelate Complexes as Versatile Links in Supramolecular Chemistry

Erica Giraldi

Clathrochelate complexes have been widely investigated with different size and shape and used as building blocks for the obtainment of discrete supramolecular architectures. These clathrochelate compl
EPFL2021

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Multicomponent Assembly of Boronic Acid-Based Macrocycles, Cages, and Polymers

Burçak Içli

This work describes the synthesis and characterization of boronic acid-based supramolecular structures. Different reversible interactions such as boronate ester formation, imine condensation and dativ
EPFL2012
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Related concepts (7)
Triflate
In organic chemistry, triflate (systematic name: trifluoromethanesulfonate), is a functional group with the formula and structure . The triflate group is often represented by , as opposed to −Tf, which is the triflyl group, . For example, n-butyl triflate can be written as . The corresponding triflate anion, , is an extremely stable polyatomic ion; this comes from the fact that triflic acid () is a superacid; i.e. it is more acidic than pure sulfuric acid, already one of the strongest acids known.
Organoboron chemistry
Organoboron chemistry or organoborane chemistry is the chemistry of organoboron compounds or organoboranes, which are chemical compounds of boron and carbon that are organic derivatives of borane (BH3), for example trialkyl boranes. . Organoboron compounds are important reagents in organic chemistry enabling many chemical transformations, the most important ones being hydroboration and carboboration. Reactions of organoborates and boranes involve the transfer of a nucleophilic group attached to boron to an electrophilic center either inter- or intramolecularly.
Suzuki reaction
The Suzuki reaction is an organic reaction, classified as a cross-coupling reaction, where the coupling partners are a boronic acid and an organohalide and the catalyst is a palladium(0) complex. It was first published in 1979 by Akira Suzuki, and he shared the 2010 Nobel Prize in Chemistry with Richard F. Heck and Ei-ichi Negishi for their contribution to the discovery and development of palladium-catalyzed cross-couplings in organic synthesis. This reaction is also known as the Suzuki–Miyaura reaction or simply as the Suzuki coupling.
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