Preparation and Enantioselectivity Binding Studies of a New Chiral Cobalt(II)porphyrin-Tröger's Base Conjugate

A new bis[cobalt(II)porphyrin]-Troger's base conjugate was studied as a potential receptor for methyl esters of several amino acids. The conjugate was prepared as racemate, and then resolved via preparative high-performance liquid chromatography (HPLC) on a chiral column. The high affinity to lysine, histidine, and proline methyl esters was found by complexation studies followed by UV-Vis spectroscopy. The studies of pure enantiomers, followed by UV-Vis and electronic circular dichroism spectroscopy, revealed the highest enantioselectivity for lysine methyl ester. Chirality 26:361–367, 2014. © 2014 Wiley Periodicals, Inc.