Benzoboroxoles as Efficient Glycopyranoside-Binding Agents in Physiological Conditions: Structure and Selectivity of Complex Formation

In contrast to normal boronic acids, o-hydroxymethyl phenylboronic acid (benzoboroxole) has the capability of complexing glycopyranosides efficiently in neutral water. The measurement of association constants with a panel of model hexopyranosides indicates that the preferred mode of binding is throu...

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Bibliographic Details
Published in:Journal of organic chemistry 2008-09, Vol.73 (17), p.6471-6479
Main Authors: Bérubé, Marie, Dowlut, Meenakshi, Hall, Dennis G
Format: Article
Language:English
Subjects:
Binding Sites
Boronic Acids - chemistry
Boronic Acids - metabolism
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Cell Membrane - chemistry
Cell Membrane - metabolism
Chemistry
Coordination compounds
Exact sciences and technology
Galactose - chemistry
Galactose - metabolism
Heterocyclic compounds
Hydrogen Bonding
Hydrogen-Ion Concentration
Inorganic chemistry and origins of life
Magnetic Resonance Spectroscopy
Miscellaneous
Oligosaccharides - chemistry
Oligosaccharides - metabolism
Organic chemistry
Preparations and properties
Solubility
Stereoisomerism
Structure-Activity Relationship
Thermodynamics
Water - chemistry
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Summary:In contrast to normal boronic acids, o-hydroxymethyl phenylboronic acid (benzoboroxole) has the capability of complexing glycopyranosides efficiently in neutral water. The measurement of association constants with a panel of model hexopyranosides indicates that the preferred mode of binding is through a cis-3,4-diol, such as that found in galactopyranosides, and mass spectrometric studies support a 1:1 binding stoichiometry. The complexation of glucopyranosides is weaker, and they are bound through their 4,6-diol unit. Although several factors may explain the exceptional carbohydrate-binding behavior of this class of hemiboronic acids, the relatively high Lewis acidity of benzoboroxoles is a likely contributing factor along with subtle factors such as intramolecular hydrogen bonds with other hydroxyl groups in the resulting anionic complex. These results with hexopyranosides suggest that biologically relevant cell-surface oligosaccharides could be targeted in water using oligomeric benzoboroxole receptors.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo800788s