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-(1-phenyl)ethylammonium bromide were in fact able to convert the racemic mixture of bilirubin-IXalpha 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.
Bombelli
Cecilia
C
CNR, Istituto di Metodologie Chimiche and Dipartimento di Chimica "La Sapienza", P.le A. Moro 5, 00185 Roma, Italy.
Bernardini
Carlotta
C
Elemento
Gioia
G
Mancini
Giovanna
G
Sorrenti
Alessandro
A
Villani
Claudio
C
D000473:Alkanes / Q000737:chemistry; D001663:Bilirubin / Q000737:chemistry; D006842:Hydrocarbons, Brominated / Q000737:chemistry; D008567:Membranes, Artificial; D008823:Micelles; D008954:Models, Biological; D008958:Models, Molecular; D008968:Molecular Conformation; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D000473:Alkanes; D006842:Hydrocarbons, Brominated; D008567:Membranes, Artificial; D008823:Micelles; D000644:Quaternary Ammonium Compounds; D001663:Bilirubin