The Things You Need To Know About Boronic Acids
|11.6.2020||Posted by electronics51 under Advertising & Marketing|
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.
What’s the function about boronic acid?
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.
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. 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 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.
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 by condensation with alcohols and diols. Phenylboronic acid can be selfcondensed to the cyclic trimer called triphenyl anhydride or triphenylboroxin.
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