Complexation of amino acids derivatives in water by calix[4]arene phosphonic acids

• DOI: 10.1007/s10847-008-9434-4
• Publication Date: 2008-04-03T08:55:59Z
• Authors: Joanna Dziemidowicz; Dariusz Witt; Janusz Rachoń
• Keywords: Calixarene; Phosphate buffered saline

Series of the calix[4]arene phosphonic acids with various substituents at the lower rim was synthesized. Complexing properties of these receptors towards methyl esters of six amino acids strongly depended on the calix[4]arene conformation flexibility. The complex formation processes were monitored using 1H NMR spectroscopy (deuterated phosphate buffer at pD 7.3, 22 °C) and association constant values were evaluated. Inherently mobile calix[4]arene molecule 3 occurred in cone conformation in aqueous solution turned out to be more effective in complexation of the basic amino acids methyl esters compared to the rigid 2 and flexible 4. Mixed 1:2 and 2:1 (host–guest) complexes were observed for compound 1 with all amino acids methyl esters.