Glucose selectivity

Kamati VV, Gao X, Gao S, Yang W, Ni W, Sankar S, Wang B. A glucose-selective fluorescence sensor based on boronic acid-diol recognition. Bioorganic and Medicinal Chemistry Letters 2002, 12, 3373-3377. 

Selective reduction of ketoses. In the presence of a large excess of CeCl3, sodium borohydride reduces D-fructose (1) in the presence of D-glucose selectively to a mixture of D-mannitol and D-glucitol (2).2... 

Giza BK, Scott TR. 1983. Blood glucose selectively affects taste-evoked activity in rat nucleus tractus solitarius. Physiol Behav31 643-650. 

H. Eggert, J. Frederiksen, C. Morin, J. C. Norrild, A new glucose-selective fluorescent bisboronic acid. First report of strong a-furanose complexation in aqueous solution at physiological pH, Journal of Organic Chemistry 1999, 64, 3846. 

Bis-boronate 7 forms a 1 1 complex with glucose selectively relative to other saccharides, and its enhanced fluorescence can be used as a glucose-selective molecular fluorescence sensor at physiological glucose concentrations." ... 

The use of boronic acids in the development of fluorescent sensors for saccharides is a comparatively new field (Scheme 3). Following the first report by Yoon and Czamik" o-glucose selectivity was achieved in 1994 by James et al. A year later, this was followed up by enan-tioselective saccharide recognition. The intervening years have seen the field grow to the point where hundreds of publications now report on boronic acid-saccharide recog-... 

James prepared chiral boronic acid-based sensors R,R-and S,S-13, which are direct structural derivatives of the original o-glucose-selective sensor The pH... 

James has used alizarin red S in the design of a o-glucose-selective fluorescent assay.Sensor 62 and alizarin red S show a sixfold enhancement over PBA for o-glucose. Sensor 62 can also be used at a concentration 10 times lower than PBA. The observed stability constants (/fobs)... 

James has prepared a ferrocene monoboronic acid 64 and diboronic acid 65 as electrochemical saccharide sensors. The monoboronic acid system 64 has also been prepared and proposed as an electrochemical sensor for saccharides by Norrild and Sotofte. The electrochemical saccharide sensor 65 contains two boronic acid units (saccharide selectivity), one ferrocene unit (electrochemical read out), and a hexamethylene linker unit (for D-glucose selectivity). The electrochemical sensor 65 displays enhanced D-glucose (40 times) and D-galactose (17 times) selectivity when compared to the monoboronic acid 64. 

Figure 5.8 Structure of the glucose-selective sensor component 3,3 -o-BBV. ...

Wang has employed the template approach using monomer 84 to prepare a fluorescent polymer with enhanced selectivity towards D-fructose [161,162]. Appleton has used a similar approach using monomer 85 to prepare a D-glucose selective polymer [77]. The Appleton polymer clearly shows the value of the imprinting technique. Here, the selectivity of the monomer for D-fructose over D-glucose has been reversed in the polymeric form. 

James and co-workers have developed polymer sensors by grafting a solution based D-glucose selective receptor 27d to a polymer support [78]. The major difference between the polymer-bound system 86 and solution-based system 27d is the D-glucose selectivity, which drops for polymer 86 (whereas the selectivity with other saccharides is similar to those observed for compound 27d). However, the polymeric system still has enhanced D-glucose selectivity (nine times) over the monoboronic acid model compound. The reduced binding of 86 for D-glucose has been attributed to the proximity of the receptor to the polymer backbone. 

Fluorescent sensors based on monoboronic acid often exhibit selectivity for fructose. The development of glucose-selective chemosensors in the medical field is being pursued vigorously because of the need to measure blood glucose levels for the management of diabetes. 

The design of a molecular recognition site that allows the capture of one glucose molecule by two boronic acid residues is expected to increase the selectivity for glucose. As it is difficult for other monosaccharides such as fructose to form esters in a 1 2 ratio, glucose selectivity can be enhanced. James et al. developed a boronic acid fluorescent probe 1 (Figure 13.2) that exhibits glucose selectivity via a two-point... 

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