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The Things You Need To Know About Boronic Acids
By: Hunan Huateng Pharmaceutical Co. Ltd.
A boronic acid 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 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 (https://en.wikipedia.org/
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.
Huateng Pharma (https://en.huatengsci.com/
Hunan Huateng Pharmaceutical Co. Ltd.
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