A diglucosylated fluorinated surfactant to handle integral membrane proteins in aqueous solution

The use of fluorinated surfactants as efficient tools for handling membrane proteins in aqueous media was demonstrated many years ago. The work reported herein deals with the synthesis of a new sugar-based surfactant bearing two glucose moieties and labelled F6-DigluM. The synthesis of F6-DigluM is based on a one-pot reduction/alkylation of a fluorinated thioacetate onto an acrylamido-type polar head precursor, using NaBH4 in refluxing methanol. Its physical–chemical properties in aqueous solution were studied by surface tension measurement, dynamic light scattering and analytical ultracentrifugation. F6-DigluM exhibits a critical micellar concentration of ∼0.4 mM and self-assembles into small and well-defined aggregates, very likely to globular micelles. Finally, the homogeneity and the stability of complexes of bacteriorhodopsin and F6-DigluM over time were observed, demonstrating that F6-DigluM is a suitable tool for biochemical applications.

Graphical abstractThe synthesis of F6-DigluM is based on a one-pot reduction/alkylation of a fluorinated thioacetate onto an acrylamido-type polar head precursor, using NaBH4/methanol under reflux. F6-DigluM exhibits a critical micellar concentration of ∼0.4 mM and forms small and well-defined globular micelles. The homogeneity and the stability of bacteriorhodopsin solubilised in F6-DigluM were observed.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► We have synthesized a new diglucosylated fluorinated surfactant (F6-DigluM). ► F6-DigluM exhibits a critical micellar concentration of ∼0.4 mM. ► F6-DigluM forms small and well-defined globular micelles. ► Bacteriorhodopsin/F6-DigluM complexes are homogeneous and monodisperse. ► Bacteriorhodopsin is stable over time in F6-DigluM solution.