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Issue 1, 2013
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Lewis acidity and sugar receptor activity of 3-amino-substituted benzoxaboroles and their ortho-aminomethylphenylboronic acid analogues

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Abstract

The pKas as well as apparent binding constants of several 3-amino-substituted benzoxaboroles with alizarin red S (ARS) and some biologically important sugars have been evaluated and compared with that of the parent aminomethylphenylboronic acids. The investigated benzoxaboroles reveal lower acidity than the corresponding boronic acids. All the studied boronic compounds display the usual order of apparent binding constant values with glucose, galactose and fructose. The X-ray structure of the model catechol ester of the morpholinylmethylphenylboronic acid has been determined. The molecules are monomeric zwitterions with a tetracoordinated boron atom. The intermolecular interactions have been described with the aid of the Hirshfeld surface analysis.

Graphical abstract: Lewis acidity and sugar receptor activity of 3-amino-substituted benzoxaboroles and their ortho-aminomethylphenylboronic acid analogues

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Publication details

The article was received on 03 Aug 2012, accepted on 27 Sep 2012 and first published on 01 Oct 2012


Article type: Paper
DOI: 10.1039/C2NJ40687J
Citation: New J. Chem., 2013,37, 188-194
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    Lewis acidity and sugar receptor activity of 3-amino-substituted benzoxaboroles and their ortho-aminomethylphenylboronic acid analogues

    A. Adamczyk-Woźniak, K. M. Borys, I. D. Madura, A. Pawełko, E. Tomecka and K. Żukowski, New J. Chem., 2013, 37, 188
    DOI: 10.1039/C2NJ40687J

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