engleski

Synthesis and complexation properties of calix[4]arene glycoconjugates

Calixarenes are a class of supramolecular cavitands that can be easily functionalized to give receptors for ionic and neutral species. In many papers published so far their use has been tested in a wide range of applications, from simple host-guest interactions to biomimetics and catalysis. Structural evolution of these compounds has led to more selective receptors with improved physico-chemical properties. Most of the synthesized calixarene ionic receptors are not sufficiently soluble in water which makes their use quite limited [1]. Water-soluble calixarenes usually own this property to the introduced easily-ionized sulfonic groups. In the scope of this work novel neutral and water-soluble ligands 1–3 (Figure 1) were designed and prepared, and their complexation with alkali-metal cations was investigated. Glucose was embedded in the structure as hydrophilic domain whereas secondary and tertiary amides served as cation- binding sites. The latter motifs were used since the calixarene derivatives comprising such groups were previously proven to form highly stable complexes [2]. Complexation reactions with alkali-metal cations were studied in water, methanol, and formamide thus giving insight into the solvation as well as intra- and intermolecular hydrogen bonds effects. Several techniques were used, such as UV spectrophotometry, isothermal titration calorimetry and NMR spectroscopy.

calixarene ; complexation ; glycoconjugate

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