Abstract
MEANS of distinguishing between enantiomers of a chiral molecule are of critical importance in many areas of analytical chemistry and biotechnology, particularly in drug design and synthesis. In particular, solution-based sensor systems capable of chiral recognition would be of tremendous pharmaceutical value. Here we report the chiral discrimination of D- and L -monosaccharides using a designed receptor molecule that acts as a sensor by virtue of its fluorescent response to binding of the guest species. Our receptor contains boronic acid groups that bind saccharides by covalent interactions; such receptor systems have been much studied previously1–6 for complexation of saccharides, and have an advantage over others based on hydrogen-bonding interactions7–11, for which polar protic solvents such as water can compete with guest binding. Our molecular sensor also incorporates a fluorescent naphthyl moiety; binding of each enantiomer of the monosaccharides alters the fluorescence intensity to differing degrees, enabling them to be distinguished. These water-soluble molecular sensors might form the basis of a quantitative and selective analytical method for saccharides.
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References
Deng, G., James, T. D. & Shinkai, S. J. Am. chem. Soc. 116, 4567–4572 (1994).
James, T. D., Sandanayake, K. R. A. S. & Shinkai, S. J. chem. Soc., chem. Commun. 477–478 (1994).
James, T. D., Sandanayake, K. R. A. S. & Shinkai, S. Angew. Chem. 33, 2207–2209 (1994).
Yoon, J. & Czarnik, A. W. J. Am. chem. Soc. 114, 5874–5875 (1992).
Morin, G. T., Hughes, M. P., Paugam, M.-F. & Smith, B. D. J. Am. chem. Soc. 116, 8895–8901 (1994).
Wulff, G. Pure appl. Chem. 54, 2093–2102 (1982).
Rebek, J. Jr Angew. Chem. 29, 245–255 (1990).
Goswami, S. & Hamilton, A. D. J. Am. chem. Soc. 111, 3425–3426 (1989).
Kelly, T. R., Zhao, C. & Bridger, G. J. J. Am. chem. Soc. 111, 3744–3745 (1989).
Etter, M. C. & Adsmond, D. A. J. chem. Soc., chem. Commun. 589–591 (1990).
Aoyama, Y., Tanaka, Y., Toi, H. & Ogoshi, H. J. Am. chem. Soc. 110, 634–635 (1988).
Bissel, R. A. et al. Top. Curr. Chem. 168, 223–264 (1993).
Czarnik, A. W. Fluorescent Chemosensors for Ion and Molecular Recognition (ACS Books, Washington DC, 1993).
Lorand, J. P. & Edwards, J. D. J. org. Chem. 24, 769–774 (1959).
Irie, M., Yorozu, T. & Hayashi, K. J. Am. chem. Soc. 100, 2236–2237 (1978).
Yorozu, T., Hayashi, K. & Irie, M. J. Am. chem. Soc. 103, 5480–5484 (1981).
Brunner, H. & Goldbrunner, J. Chem. Ber. 122, 2005–2009 (1989).
Bruner, H. & Wultz, K. New J. Chem. 16, 57–61 (1992).
Brunner, H. & Schiessling, H. Angew. Chem. 33, 125–126 (1994).
Perrin, D. D. & Dempsey, B. Buffers for pH and Metal Ion Control Ch. 6 (Chapman & Hall, London, 1974).
Fery-forgues, S., LeBris, M.-T., Guette, J.-P. & Valeur, B. J. phys. Chem. 92, 6233–6237 (1988).
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James, T., Samankumara Sandanayake, K. & Shinkai, S. Chiral discrimination of monosaccharides using a fluorescent molecular sensor. Nature 374, 345–347 (1995). https://doi.org/10.1038/374345a0
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DOI: https://doi.org/10.1038/374345a0
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