Triazole linked lower rim glycosyl appended 1,3-calix[4]arene conjugates: synthesis, characterization, and their interaction with jacalin

Abstract

Triazole linked lower rim galactosyl and lactosyl appended calix[4]arene conjugates have been synthesized by 1,3 dipolar addition of glycosyl azide and calix[4]arene alkyne. All these conjugates were characterized by ¹H and ¹³C NMR, IR and mass spectrometry. Interaction of amino acids with the galactosyl conjugate of calix[4]arene (5) was studied using absorption and ¹H NMR techniques. Absorption studies showed that Trp interacts with triazole ring of 5. This was further confirmed by 1H NMR study which showed an upfield shift in the triazole proton of 5 upon titrating with Trp. The preliminary studies of interaction of these conjugates with Jacalin were demonstrated by fluorescence and circular dichroism (CD) spectroscopy techniques.