Highly effective receptors showing di- vs. monosaccharide preference

Organic & Biomolecular Chemistry
Monika Mazik, Arno C Buthe

Abstract

Receptors and , 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 and 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.

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Citations

May 21, 2010·Beilstein Journal of Organic Chemistry·Monika Mazik, André Hartmann
Nov 6, 2015·European Journal of Medicinal Chemistry·Eva Rivero-BucetaAna San-Félix
Jul 11, 2013·Chemistry : a European Journal·Oscar FrancesconiStefano Roelens
Aug 3, 2018·Chemistry : a European Journal·Kalanidhi PalanichamyAdam B Braunschweig
May 8, 2009·Organic & Biomolecular Chemistry·Monika Mazik, Arno C Buthe
May 6, 2009·Angewandte Chemie·Hans-Jörg Schneider
Apr 8, 2020·Chemistry : a European Journal·M Fernando BravoAdam B Braunschweig
Oct 24, 2020·Biochemistry·M Fernando BravoAdam B Braunschweig
Jun 26, 2008·The Journal of Organic Chemistry·Monika Mazik, Andrè Hartmann
Mar 18, 2011·The Journal of Organic Chemistry·Hajime AbeMasahiko Inouye

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