New Amphiphiles Functionalized with Oligo and Olysaccharides

This book reports the preparation and characterization of new rod-coil amphiphiles functionalized with oligo- and polysaccharides through Huisgen 1,3-dipolar cycloaddition reactions between species functionalized by an azide group on one side and an terminal alkyne on the other catalyzed by copper. The amphiphiles were synthesized and characterized based on different hydrophobic parts conjugated with the polymer poly(ethylene oxide) PEO with a hydrophilic spacer arm and the oligo- and polyssaccharides 2-propargyl-2-acetamido- 2-deoxy--D-glucopyranose (GlcNAc) and propargyl -D-galactopyranosyl-(1-4)--D-glucopyranose (Lac). The amphiphiles synthesized were characterized in terms of their chemical structure and composition through nuclear magnetic resonance (NMR),mass spectroscopy (MALDI-TOF-MS and ESI-MS)and high resolution mass spectroscopy (HRMS). After the dissolution in water, the amphiphiles self-associate in highly regular micelles with an average diameter of 2RH~10nm. Dynamic light scattering (DLS), transmission electron microscopy (TEM) and small angle x-ray scattering (SAXS) were used in order to investigate the structure and dynamics of these saccharide amphiphiles.