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[摘要]：(Hemi)fluorinated hydrophobic chains have been found to minimize the denaturating propensity of surfactants toward membrane proteins. The work reported herein deals with the synthesis of a new series of non-ionic glucose-based surfactants endowed with a hybrid hemifluorocarbon chain. The convergent synthesis is based on a one-pot redn./alkylation of hemifluorinated thioacetate and glucosylated trishydroxymethyl acrylamidomethane using NaBH4 in methanol. This "mild" alkylation was studied in order to improve yields and to pass up the use of an excess of com. unavailable hemifluorinated thiols. The phys.-chem. properties in aq. soln. of this novel series were studied by surface tension measurement and dynamic light scattering (DLS), as well as their behavior upon reverse-phase chromatog., and were compared with those of their hydrogenated and perfluorinated analogs. The atypical effect of the addnl. Et tip to the fluorinated chain was demonstrated by higher crit. micellar concn. values and abnormal hydrophobicities measured by reverse-phase chromatog. Moreover, according to Israelachvili's concept, DLS studies showed that surfactants bearing bulkier polar head self-assemble into small and well-defined aggregates, suggesting the formation of spherical micelles rather than the cylindrical ones usually obsd. with classical fluorinated surfactants. |
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