Concentration as the Switch for Chiral Recognition in Biomembrane Models.

Here we report on the investigation of the expression of chirality in micellar aggregates formed by enantiopure N-alkyl-N,N-dimethyl-N-(1-phenyl)ethyammonium bromides, 1, that had already been used as media for diastereoselective reactions and as models for investigating chirality in biomembranes. As a probe for detecting the chirality of the aggregates, we used bilirubin-IXR, a bile pigment that assumes a dissymmetric ridgetile structure stabilized by intramolecular hydrogen bonds and is, therefore, a racemic mixture of equilibrating enantiomers.