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Artificial Receptors as Chemosensors for Carbohydrates

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Host-Guest Chemistry

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 218))

Abstract

As the chemistry of saccharides and related molecular species plays a significant role in the metabolic pathways of living organisms, detecting the presence and concentration of biologically important sugars in aqueous solution is necessary in a variety of medicinal and industrial contexts. The recognition of d-glucose is of particular interest, for example in the monitoring of diabetics. Recent research provides clear evidence that tight control of blood sugar levels in diabetics sharply reduces the risk of long term complications, which include blindness, kidney failure, heart attacks and even gangrene and amputation of the limbs. Current enzymatic detection methods of sugars offer specificity for only a few saccharides; additionally, enzyme based sensors are unstable in harsh conditions. Phenylboronic acid has been known for 120 years. However, it took until 1959 for the first quantitative evaluation of saccharide boronic acid interactions. Boronic acids react with 1,2 or 1,3 diols of saccharides to form five- or six-membered cyclic esters in non-aqueous or basic aqueous media. The stable boronic acid-based saccharide receptors offer the possibility of creating saccharide sensors ‘chemosensors’ which are selective and sensitive for any chosen saccharide.

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Authors and Affiliations

  1. Department of Chemistry, University of Bath, BA2 7AY, UK

    Tony D. James

  2. Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, Fukuoka, 812-8581, Japan

    Seiji Shinkai

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  1. Tony D. James
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  1. Instituto de Investigaciones QuĂ­micas, Consejo Superior Investigaciones Cientificas, CSIC, Isla de la Cartuja, 41092, Sevilla, Spain

    Soledad Penadés

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James, T.D., Shinkai, S. (2002). Artificial Receptors as Chemosensors for Carbohydrates. In: Penadés, S. (eds) Host-Guest Chemistry. Topics in Current Chemistry, vol 218. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-45010-6_6

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