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Reference type: Journal
Authors: Adbo K, Andersson HS, Ankarloo J, Karlsson JG, Norell MC, Olofsson L, Svenson J, Ortegren U, Nicholls IA
Article Title: Enantioselective Tröger's base synthetic receptors.
Publication date: 1999
Journal: Bioorganic Chemistry
Volume: 27
Issue: (5)
Page numbers: 363-371.
DOI: 10.1006/bioo.1999.1136

Abstract: Synthetic receptors selective for the enantiomers of Troger'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 K-diss 0.7 +/- 0.1 mM at 293 K in chloroform. The synthetic receptors demonstrated enantioselectivity when used as HPLC chiral stationary phases; enantioseparation factors (alpha) 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. (C) 1999 Academic Press
Template and target information: Tröger's base, Troger's base, 2,8-dimethyl-6H,12H-5,11-methanodibenzo[b, f ][1,5]diazocine


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