Fluorescent boronic acids

Burnett, et al. (1980) Synthesis of a fluorescent boronic acid which reversibly binds to cell walls, etc. Biochem. Biophys. Res. Comm. 96, 157-162. 

In the search for a long-wavelength fluorescent boronic acid receptor, Mohr has prepared a series of fluorescent hemicyanine dyes receptors 8a-c. Hemicyanine 8a was the best receptor with a binding constant of 280 M , while 8b was 40 M and 8c was 200 M with D-fructose. ... 

Chiral Recognition Using Fluorescent Boronic Acids Chemosensors... 

Figure 6.1 Typical Wolf-type fluorescent boronic acid chemosensors (1-3) for recognition of saccharides.

In 1995, James and Shinkai et al. ° used Binol based fluorescent boronic acid chemosensors for enantioseleetive recognition of monosaccharides, such as glucose. The Binol-based boronie acid sensors are [R)- and (Sj-isomers, whieh demonstrates mirror responses to the enantiomers of o-glueose and L-glueose. The enantioselectivity ean be unambiguously demonstrated by this mirror response. The origin of the enantioselectivity was attributed to the different strain for the cyclic adducts of the bis-boronic aeid with glueose. 

Y. Seon Jeong and K. JinaLee, Fluorescent boronic acid-modified polymer nanoparticles for enantioselective monosaccharide detection. Anal Methods, 2012, 4(4), 913-918. 

In a novel approach Hamachi coupled a natural receptor protein (Concanavalin A - ConA) with a fluorescent boronic acid PET system to prepare a semi-synthetic biosensor (46, Figure 12.11) [112]. The system illustrates how both synthetic and natural systems can be combined to generate biosensors with enhanced selectivity towards specific oligosaccharides. Observed f pp for 46 were 708 M" for D-fructose and 151000 M" for D-palatinose in water at pH 7.5 (HEPES buffer). 

FIGURE 13.4 Fluorescent boronic acid-y-CD complex sensor. (Sources A. J. Tong et al.. Anal. Chem., 73, 1530-1536 (2001). Copyright (2001), American Chemical Society. With permission. M. Kumai et al.. Anal. ScL, 28, 121-126 (2012), Copyright (2012), The Japan Society of Analytical Chemistry. With permission.)... 

Suenaga, H., Mikami, M., Sandanayake, K. R. A. S., and Shinkai, S. (1995) Screening of fluorescent boronic acids for sugar sensing which show a large fluorescence change. Tetrahedron Lett., 36,4825-4828. 

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