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

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.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Glycosyl appended calix[4]arene conjugates have been synthesized in good yields. ► Amino acid interaction with galactosyl conjugate of calix[4]arene were studied. ► Preliminary interaction studies of these conjugates with lectins were carried out.