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Issue 22, 2004
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Enantioselective synthetic thalidomide receptors based upon DNA binding motifs

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Abstract

A series of molecularly imprinted polymer (MIP) synthetic receptors selective for the sedative thalidomide (5) have been designed and synthesized based upon the functional monomer 9-(2′-methacryloyloxyethyl)adenine (2). 1H-NMR studies were used to establish the existence of DNA-like binding interactions between 2 and the template (5). A series of ethylene glycol dimethacrylate cross-linked copolymers was synthesized using either 2 or methacrylic acid, or a combination of these functional monomers. Zonal HPLC studies demonstrated enantioselectivity (α = 2.11) and ligand selectivity which could be attributed to the interaction of 2 with the imide moiety of 5. Compound 2 provided a more significant contribution to the binding of 5 than methacrylic acid, though a combination of these two functional monomers resulted in improved enantioselectivity. Frontal chromatographic and batch binding studies confirmed the observed differences in affinity of the imprinted and reference polymers for the template.

Graphical abstract: Enantioselective synthetic thalidomide receptors based upon DNA binding motifs

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Publication details

The article was received on 28 May 2004, accepted on 02 Sep 2004 and first published on 11 Oct 2004


Article type: Paper
DOI: 10.1039/B407996E
Citation: Org. Biomol. Chem., 2004,2, 3374-3378
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    Enantioselective synthetic thalidomide receptors based upon DNA binding motifs

    J. P. Rosengren, J. G. Karlsson and I. A. Nicholls, Org. Biomol. Chem., 2004, 2, 3374
    DOI: 10.1039/B407996E

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