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Molecules 2013, 18(5), 6101-6112; doi:10.3390/molecules18056101
Short Note

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

1,†, 2,3,†, 2,3,* , 1, 2,3 and 1,*
1 Unité Mixte de Recherche "Réactions Sélectives et Applications", CNRS—Université de Reims Champagne-Ardenne, Boîte n 44, B.P. 1039, F-51687 Reims, France 2 Unité de Chimie Biologique Industrielle, Gembloux Agro-Bio Tech, Université de Liège, 2, Passage des Déportés, B-5030 Gembloux, Belgium 3 Centre de Biophysique Moleculaire Numerique, Gembloux Agro-Bio Tech, Université de Liège, 2, Passage des Déportés, B-5030 Gembloux, Belgium These authors have equally contributed to this work.
* Authors to whom correspondence should be addressed.
Received: 2 April 2013 / Revised: 22 April 2013 / Accepted: 15 May 2013 / Published: 22 May 2013
(This article belongs to the Section Organic Synthesis)
Download PDF [323 KB, 18 June 2014; original version 18 June 2014]

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 rhamnose; glycosylation; metathesis; surfactant; bolaform; interfacial properties
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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.

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