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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.

SUBMITTER: Razgulin AV

PROVIDER: S-EPMC4342307 | biostudies-literature | 2015 Apr

REPOSITORIES: biostudies-literature

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Synthesis, emulsification and self-assembly properties of sugar-containing semifluorinated amphiphiles.

Razgulin Andrew V AV Mecozzi Sandro S

Carbohydrate research 20150114

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. ...[more]

PMID: 25658061

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