4.5 Article

A glucose-selective fluorescence sensor based on boronic acid-diol recognition

Journal

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volume 12, Issue 23, Pages 3373-3377

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0960-894X(02)00767-9

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Funding

  1. NCI NIH HHS [N01-CO-27184, CA88343] Funding Source: Medline
  2. NIDDK NIH HHS [DK55062] Funding Source: Medline

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A glucose selective diphenylboronic acid fluorescent sensor (10a) vith a K-a of 1472 M-1 has been synthesized and evaluated. This sensor shoals a 43- and 49-fold selectivity for glucose over fructose and galactose, respectively. The binding affinity improvement is about 300-fold and the selectivity. improvement for glucose over fructose is about 1400-fold compared vith the monoboronic acid compound. phenylboronic acid. H-1 NMR studies indicate that sensor 10a binds with alpha-D-glucofuranose in a bidentate manner (1:1 ratio). (C) 2002 Elsevier Science Ltd. All rights reserved.

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