Synthesis and physico-chemical characterization of bolaamphiphiles derived from alkenyl D-xylosides

The two step synthesis of a new series of bolaamphiphiles derived from alkenyl D-xylosides is described. Yields between 57 and 90% have been reached. Aggregation behavior and membrane interaction properties of a particular sugar-bolaform composed of two xylose heads connected by an ether link to a hydrophobic chain comprising 18 carbon atoms and an insaturation were studied. Its CAC value (similar to 0.05 mM) is low compared to those of conventional surfactants. Thermodynamic analysis has revealed that the aggregation phenomenon is mainly driven by an entropy process. The compound is able to interact with DPPC monolayers, in particular if their surface pressure is >= 15 mN m(-1). Our results highlight the potential of this bolaamphiphile as surfactant and membrane interacting agent.