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Sythesis of novel lipophilic mannosides and their complexation with β-cyclodextrin

Cyclodextrines (CDs) have been studied due to their ability to host wide variety of hydrophobic compounds in water and increase their solubility in water, hence bioavailability [1]. Recently, we reported the synthesis of adamantyl glycosides and the thermodynamic parameters of their complexation with β-CD in water [2] Our present investigations have been directed to the complexation of amphiphilic glycosides, namely, adamant-1- yl, cyclohexyl and benzyl 2-(α-D- mannopyranosyloxy)acetates with β-CD in water and in organic solvent. In this work we present the synthesis of novel amphiphilic mannosylated derivatives of acetic acid with different alkyl parts (Figure 1). The esters were prepared by the reaction of acetylated mannopyranose and corresponding esters of bromoacetic acid with linear, branched or cyclic alkyl parts. Their complexation with β- CD was studied by means of titration calorimetry and NMR spectroscopy. Solvents used in calorimetric experiments were strongly hydrogen bonded (water, alcohols) in which the inclusion of similar guests in β-CD is still largely unexplored. The thermodynamic parameters of complexation (reaction enthalpies, standard reaction entropies, binding constants) were determined. Obtained results provide a deeper insight in correlations between guest structure and its complexation thermodynamics in examined solvents.

amphiphilic mannosides ; beta-cyclodextrin ; titration calorimetry ; NMR spectroscopy

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