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

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

Marie Bérubé, Meenakshi Dowlut, Dennis G Hall

J Org Chem. 2008 Sep 5;73(17):6471-9.

PMID: 18549270

Abstract:

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP87199153	3-(Hydroxymethyl)phenylboronic acid		87199-15-3	Price

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