Saccharides boronic acid-based receptors/sensor

James, T.D. (2005) Boronic Acid-Based Receptors and Sensors For Saccharides, in Boronic Acids (ed. D.G. Hall), Wiley-VCH, Weinheim, Ch. 12,... 

I 12 Boronic Acid-based Receptors and Sensors for Saccharides... 

T.D. James, Boronic acid based receptors and sensors for saccharides, in Boronic Acids in Organic Synthesis and Chemical Biology, D.G. Hall (ed), Wiley-VCH, 2005, 441 80. 

In the design of boronic acid-based sensor systems, it has been established that two receptor units are required if saccharide selectivity is to be achieved." " Retaining the same dual boronic acid recognition units throughout, a modular system in which the linker and fluorophore units of these sensors could be modified independently needed to be developed. The use of modular or core scaffolds for saccharide recognition has been championed by James, 3ng,i 1-82 5 Hall, and Singaram. i... 

This book describes the recent efforts to develop practically useful receptors and sensors for saccharides using boronic acids. Since the first publication on glucose-selective diboronic acid-based PET sensors a decade ago, these systems have proved their worth and have come to find application at the cutting edge of medical care. 

Boronic acids RB(OH)2, boronic esters RB(OR)2, and triorganoboranes R3B have been studied extensively for the selective recognition of anions. " Moreover, arylboronic acids have proven highly useful for sensing of saccharides based on the facile formation of esters with diols, thus providing an excellent alternative to more commonly employed synthetic molecular receptors based on hydrogenbonding interactions. Absorption and fluorescence spectroscopy, circular dichroism, and cyclic voltammetry have all been successfiilly used as detection methods for organoboron sensors. 

We designed boronic acid receptor units in an AIDA-based (see Figure 5.22) fluorescent sensor array to differentiate neutral mono- and disaccharides in aqueous solution at neutral pH. With this array we were able to diseriminate among 12 saccharides at 2 mM concentration. The array consists of the... 

In the case of fluorescent PET sensors, the design is often discussed in terms of a receptor and a fluorophore separated by a spacer so as to match the Donor Bridge-Acceptor motif (Figure 17). To permit the recognition of saccharides via boronic acid complexation, the interaction between o-methylphenylboronie acids (Lewis acids) and proximal tertiary amines (Lewis bases) has been exploited, Figure 18. 

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