Synthesis of novel chiral polyamide macrocycles containing pyridyl side-arms and their molecular recognition properties

Seven novel C-2-symmetrical macrocycles containing pyridyl units have been prepared by the cyclic condensation of homochiral diamide intermediates with 2,6-pyridinedicarbonyl dichloride under high dilution at room temperature. The molecular recognition of these homochiral macrocycles for amino acid derivatives has been characterized by various spectroscopic methods such as IR, FAB-MS, fluorescence and UV-vis. The macrocycle 11 exhibited significant chiral recognition towards the enantiomers Of D- and L-alanine methyl ester hydrochlorides for which association constants have been determined. Molecular modeling was also used to simulate the interaction mode between the hosts and the guests. (C) 2003 Elsevier Science Ltd. All rights reserved.