Bolaamphiphiles Derived from Alkenyl L-Rhamnosides and Alkenyl D-Xylosides: Importance of the Hydrophilic Head

• Main Authors: Sandrine Bouquillon, Vincent Legrand, Nadia Klai, Magali Deleu, Mehmet Nail Nasir, Sylvain Gatard
• Format: Article
• Language: English
• Published: MDPI AG 2013-05-01
• Series: Molecules
• Subjects: rhamnose; glycosylation; metathesis; surfactant; bolaform; interfacial properties
• Online Access: http://www.mdpi.com/1420-3049/18/5/6101
• ISSN: 1420-3049

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.