Enantioselective Tröger's Base Synthetic Receptors

Synthetic receptors selective for the enantiomers of Tröger's base (1), a compound containing chiral nitrogen atoms, have been prepared by the molecular imprinting of 1 in methacrylic acid–ethylene glycol dimethacrylate copolymers. Spectroscopic evaluation of the self-assembly phase, prior to p...

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Bibliographic Details
Published in:Bioorganic chemistry 1999-10, Vol.27 (5), p.363-371
Main Authors: Adbo, Karina, Andersson, Håkan S., Ankarloo, Jonas, Karlsson, Jesper G., Norell, Mikael C., Olofsson, Linus, Svenson, Johan, Örtegren, Unn, Nicholls, Ian A.
Format: Article
Language:English
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Summary:Synthetic receptors selective for the enantiomers of Tröger's base (1), a compound containing chiral nitrogen atoms, have been prepared by the molecular imprinting of 1 in methacrylic acid–ethylene glycol dimethacrylate copolymers. Spectroscopic evaluation of the self-assembly phase, prior to polymerization, demonstrated the formation of template-functional monomer adducts of Kdiss 0.7 ± 0.1 mM at 293 K in chloroform. The synthetic receptors demonstrated enantioselectivity when used as HPLC chiral stationary phases; enantioseparation factors (α) of up to 4.8 ± 0.2 are reported. Baseline resolution of racemic 1 was readily achieved. Furthermore, the influence of water on polymer–ligand selectivity was examined, which yielded insights into the molecular basis for ligand selectivity in these synthetic receptors.
ISSN:0045-2068
1090-2120
DOI:10.1006/bioo.1999.1136