Journal of the American Chemical Society, Vol.130, No.9, 2732-2732, 2008
Concentration as the switch for chiral recognition in biomembrane models
Chiral recognition was observed in a biomembrane model. Micellar aggregates formed by enantiopure N-alkyl-N,N-dimethyl-N-(l-phenyl)ethylammonium bromide were in fact able to convert the racemic mixture of bilirubin-IX alpha into an enantiomerically enriched mixture. The stereochemical preference and the extent of enantiomeric enrichment depend on the length of the hydrophobic portion of the surfactant and on the concentration conditions, and changes in the stereochemical bias are reversible.