title: Synthesis, emulsification and self-assembly properties of sugar-containing semifluorinated amphiphiles.
abstract: Surfactants with two and three monosaccharide-based heads and a perfluoroalkyl tail have been synthesized. Perfluoroalkyl C3-symmetric triol and C2-symmetric diol were conveniently prepared via Cu-catalyzed azide-alkyne cycloaddition between a fluorous alkyne and tertiary and secondary azides, respectively. Glycosylation of the perfluoroalkyl diol and triol led to orthoester-type structures, which were evaluated for their capacity to stabilize aqueous emulsions of highly fluorinated anesthetics. The self-assembly properties of the tri-sugar amphiphile were examined by transmission electron microscopy.
authors: Department of Chemistry, University of Wisconsin, 777 Highland Avenue, Madison, WI 53705, USA.
authors: Andrew V
authors: AV
authors: Razgulin
authors: Department of Chemistry, University of Wisconsin, 777 Highland Avenue, Madison, WI 53705, USA; School of Pharmacy, University of Wisconsin, 777 Highland Avenue, Madison, WI 53705, USA. Electronic address: smecozzi@wisc.edu.
authors: Sandro
authors: S
authors: Mecozzi
mesh_terms: D000480:Alkynes / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D002384:Catalysis; D061565:Cycloaddition Reaction; D004655:Emulsions; D005466:Fluorocarbons / Q000138:chemical synthesis*; D013501:Surface-Active Agents / Q000138:chemical synthesis*
chemical_list: D000480:Alkynes; D001386:Azides; D004655:Emulsions; D005466:Fluorocarbons; D013501:Surface-Active Agents
keywords: Fluorous emulsions; Self-assembly; Semifluorinated; Sugar-based amphiphiles