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An Enantioselective Fluorescence Sensor for Glucose Based on a Cyclic Tetrapeptide Containing Two Boronic Acid Binding Sites
Author(s) -
Heinrichs Guido,
Schellenträger Marc,
Kubik Stefan
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600245
Subject(s) - chemistry , boronic acid , fluorescence , fluorescence spectroscopy , tetrapeptide , aqueous solution , enantioselective synthesis , phenylboronic acid , stereochemistry , combinatorial chemistry , organic chemistry , biochemistry , peptide , catalysis , physics , quantum mechanics
The synthesis and binding properties of carbohydrate receptor 1d , which contains two boronic acid binding sites facing each other at opposing sides of a cyclotetrapeptide cavity, are presented. According to electrospray mass spectrometry, 1 H NMR spectroscopy, and fluorescence spectroscopy, this receptor forms stable 1:1 complexes with D ‐glucose ( K a = 24800 ± 1200 M –1 ) and L ‐glucose ( K a = 11900 ± 1600 M –1 ) in water/methanol (1:1) at pH = 11.7. Complexes with D ‐galactose, D ‐mannose, and D ‐allose are significantly less stable, while D ‐fructose, D ‐ribose, and D ‐xylose cannot be bound by cooperative action of both boronic acid binding sites. Thus, 1d possesses high affinity and selectivity in glucose recognition combined with good enantioselectivity. Moreover, fluorescence of 1d is quenched upon substrate binding, which allows the use of this receptor as an optical sensor for glucose in aqueous solution. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)