Journal
TETRAHEDRON
Volume 69, Issue 52, Pages 11057-11063Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2013.11.023
Keywords
Phenylboronic acid; Chemosensor; Turn on; Sugar; Carbohydrate
Categories
Funding
- National Research Foundation [2012R1AB3000574]
- Korea Environmental Industry and Technology Institute [201200054 0013]
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A simple amino acid based compound (1) containing a phenyl boronic group and pyrene fluorophore showed an enhanced fluorescence in aqueous solutions at physiological pH through suppression of the photoinduced electron transfer from pyrene to boronic acid on carbohydrate binding. The compound exhibited an interesting fluorescence change depending on pH with decreased emission intensity at acidic pH but enhanced emission intensity at basic pH unlike the fluorescent carbohydrate chemosensors using a PET process with amine and aryl-boronic acid. We have characterized a dual role of phenylboronic acid as a receptor for carbohydrates as well as a quencher for the fluorescence of pyrene fluorophore. (C) 2013 Elsevier Ltd. All rights reserved.
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