Synthesis of Two Bicyclic Surfactants Which Form Reversed Micelles Capable of Selective Protein Extraction

摘要

Certain surfactants self-assemble in organic solvents to form reversed micelles that are capable of solubilizing hydrophilic molecules (e.g., proteins) in their aqueous interior. It is clear that there is a relationship between the structure of the monomeric surfactant and the structure of the micelle. However, the details of this relationship, important for the purposes of design, are unclear due, in part, to the fact that enantiomerically pure, conformationally restrained surfactants are not available. For example, the widely utilized surfactant AOT (di-2-ethylhexyl sulfosuccinate, Scheme 1) is a mixture of eight conformationally flexible diastereomers that would be expected to produce a complex mixture of reversed micelles which differ with respect to the ratio of the constituent AOT optical and conformational iso-mers.6 We report herein on the synthesis and self-assembly of two new conformationally-restrained surfactants. Reversed micelles comprising these surfactants were more homogeneous than those comprising AOT and extracted proteins from aqueous media in a molecular weight-dependent manner.