Issue 9, 2008
From the journal:

Organic & Biomolecular Chemistry

Highly effective receptors showing di- vs. monosaccharide preference†

Monika Mazik*a  and  Arno C. Buthea  

* Corresponding authors

a Institut für Organische Chemie der Technischen Universität Braunschweig, Hagenring 30, Braunschweig, Germany
E-mail: m.mazik@tu-bs.de
Fax: +49-531-391-8185
Tel: +49-531-391-5266

Abstract

Receptors 1 and 2, incorporating two heterocyclic recognition units as well as oxime- or hydroxymethyl-based hydrogen-bonding sites, were prepared, and their binding properties toward neutral sugars were determined. The design of these receptors was inspired by the binding motifs observed in the crystal structure of protein–carbohydrate complexes. The receptors 1 and 2 are able to recognize both mono- and disaccharides, with a strong preference for the disaccharides. Both hydrogen-bonding and interactions of the sugar CH's with the phenyl rings of the receptor contribute to the stabilisation of the receptor–sugar complexes. Molecular modeling calculations, synthesis and binding studies are described.

Graphical abstract: Highly effective receptors showing di- vs. monosaccharide preference

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Article information

DOI
https://doi.org/10.1039/B719212F
Article type
Paper
Submitted
12 Dec 2007
Accepted
14 Feb 2008
First published
14 Mar 2008

Org. Biomol. Chem., 2008,6, 1558-1568

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Highly effective receptors showing di- vs. monosaccharide preference

M. Mazik and A. C. Buthe, Org. Biomol. Chem., 2008, 6, 1558 DOI: 10.1039/B719212F

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