The Things You Need To Know About Boronic Acids

What's the boronic acid?

A boronic acid is an alkyl or aryl substituted boric acid containing a carbon – boron bond belonging to the larger class of organoboranes.

It is a compound related to  boric acid  in which one of the three  hydroxyl groups  is replaced by an  alkyl  or  aryl  group. 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 sometimes (1,3) substituted Lewis base exact (alcohol, amine, carboxylate)). The pKa of a boronic acid is ~ 9, but they can form tetrahedral boronate complexes with pKa ~ 7.

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 give a positive Ames test and act as chemical  mutagens . The mechanism of mutagenicity is thought to involve the generation of organic radicals via oxidation of the boronic acid by atmospheric oxygen

What's the application about  boronic acid?

They are sometimes 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 .

Boronic acid and its derivatives have wide range of applications and they play a potential role in bioorganic and medicinal chemistry as well as chemical biology. In bioorganic chemistry, boronic acid is a commonly used to design and synthesis of sensors which are used for detection of carbohydrates and amino acids. In chemical biology, boronic acids are utilized in the detection and sensing of the tetraserine motif in protein, recognition and sensing of peroxides and development of new MRI contrast agents and in medicinal chemistry, boronic acids are important for the preparation of inhibitors of hydrolytic enzymes in boron neutron capture therapy (BNCT), quorum sensing inhibition, antifungal agent development.

What's the difference between  boronic acid and  boronic esters? 

Boronic esters (also named boronate esters), are esters formed between a boronic acid and an alcohol. The compounds can be obtained from borate esters [17] by condensation with alcohols and diols. Phenylboronic acid can be selfcondensed to the cyclic trimer called triphenyl anhydride or triphenylboroxin.

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