Carbohydrates interaction with boronic acids

Very recently, a Japanese team reported an elegant example of molecular recognition of vesicles. It was shown by agglutination assays that vesicles equipped with boronic acid specifically bind to vesicles containing diol lipid such as phosphatidylinositol. It was demonstrated that the interaction of boronic acid vesicles and inositol vesicles is the result of selective coordination of the boronic acid and the carbohydrate diol. 

Scheme 1 Interaction between 4,4 -i r,i T-bis(benzyl-4-boronic acid)-bipyridinium dibromide with a carbohydrate at near-neutral pH...

On the basis of the supramolecular interactions between template and functional monomer in the prepolymerization complex, most MIPs can be divided into covalent as well as noncovalent MIPs. The first covalent MIP (Figure 12a) was developed by the Wulff group in the 1970s. A carbohydrate template was made to react with boronic acid monomers. The resultant complex was then copolymerized with divinylbenzene. Finally, the boronate ester was... 

In animals and humans, at intracellular pH, nearly all natural boron exists as boric acid, which behaves as a Lewis acid, and forms molecular additive compounds with amino- and hydroxy acids, carbohydrates, nucleotides, and vitamins through electron donor-acceptor interactions. In most of the commercial dietary boron supplements now available, boron is chelated with amino acids or with hydroxy acids (i.e., glycine, aspartic acid, or citric acid) in combination with vitamins. However, little is known about the molecular structure of these boron chelates. ... 

---