Abstract: The two step synthesis of a new bolaamphiphile derived from alkenyl l-rhamnosides was described. The general synthetic strategy of bolaamphiphiles derived from l-rhamnose was based on a previous work describing the synthesis of bolaamphiphiles derived from d-xylose. The conformational properties of this new compound were investigated by FTIR spectroscopy in an aqueous film in order to obtain a reference for further studies about the membrane-interacting properties. Moreover, the surface activity of this new bolaamphiphile was analyzed by Langmuir balance technology and was compared with that of the analogous bolaamphiphile derived from alkenyl D-xylosides. The findings indicate that the rhamnoside-based bolaform has an increased surface activity and a better ability to form aggregates than xyloside-based one.
Keywords: rhamnose; glycosylation; metathesis; surfactant; bolaform; interfacial properties
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Gatard, S.; Nasir, M.N.; Deleu, M.; Klai, N.; Legrand, V.; Bouquillon, S. Bolaamphiphiles Derived from Alkenyl L-Rhamnosides and Alkenyl D-Xylosides: Importance of the Hydrophilic Head. Molecules 2013, 18, 6101-6112.
Gatard S, Nasir MN, Deleu M, Klai N, Legrand V, Bouquillon S. Bolaamphiphiles Derived from Alkenyl L-Rhamnosides and Alkenyl D-Xylosides: Importance of the Hydrophilic Head. Molecules. 2013; 18(5):6101-6112.
Gatard, Sylvain; Nasir, Mehmet N.; Deleu, Magali; Klai, Nadia; Legrand, Vincent; Bouquillon, Sandrine. 2013. "Bolaamphiphiles Derived from Alkenyl L-Rhamnosides and Alkenyl D-Xylosides: Importance of the Hydrophilic Head." Molecules 18, no. 5: 6101-6112.