Enantioselective Tröger's Base Synthetic Receptors

✍ Scribed by Karina Adbo; Håkan S. Andersson; Jonas Ankarloo; Jesper G. Karlsson; Mikael C. Norell; Linus Olofsson; Johan Svenson; Unn Örtegren; Ian A. Nicholls

• Publisher: Elsevier Science
• Year: 1999
• Tongue: English
• Weight: 175 KB
• Volume: 27
• Category: Article
• ISSN: 0045-2068
• DOI: 10.1006/bioo.1999.1136

✦ Synopsis

Synthetic receptors selective for the enantiomers of Tro ¨ger'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 Ϯ 0.1 mM at 293 K in chloroform. The synthetic receptors demonstrated enantioselectivity when used as HPLC chiral stationary phases; enantioseparation factors (␣) of up to 4.8 Ϯ 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.