Examination of Structural Changes of Polymeric Amino Acid-Based Surfactants on Enantioselectivity: Effect of Amino Acid Order, Steric Factors, and Number and Position of Chiral Centers

Abstract

In this study, a large number of polymeric chiral surfactants were examined and their performances in terms of enantiomeric resolution compared for a variety of chiral analytes. The surfactants investigated in this study include all possible dipeptide combinations of the L-form of alanine, valine, leucine, and the achiral amino acid glycine (except glycine-glycine). Also included in this study were the single amino acid surfactants of alanine, valine, and leucine as well as the single chiral center dipeptide surfactant poly(sodium undecyl-L-leucine-beta-alanine) (poly L-SULbetaA). Several different aspects of polymeric dipeptide surfactants, as they pertain to chiral separations, are examined. Some of the factors investigated in this report include the effect of position and number of chiral centers, amino acid order, and steric effects.