Synthesized pharmaceutical drugs often yield racemic mixtures, meaning it contains both enantiomers of a chiral compound. These enantiomers often cause very different physiological effects. One enantiomer of a drug may produce the desired medicinal effect, whereas the other may be detrimental. For example, D-Ethambutol is used to treat Tuberculosis, whereas its enantiomer, L-Ethambutol, causes blindness. Consequently, the FDA has mandated that all chiral drugs be separated, and each enantiomer tested prior to approval and sale of product. Therefore, there is an ever-increasing need for the development of a variety chiral separation processes.<br/>Micellar Electrokinetic Chromatography (MEKC) is a well-established technique used to separate enantiomeric compounds. MEKC, as mentioned in the name, uses micelles as the pseudo stationary phase to achieve separations. In the case of chiral separations, the pseudostationary phase must be chiral. One such class of chiral pseudostationary phases are Amino Acid-Based Molecular Micelles (AABMMs). Each enantiomer of a compound can have different binding affinities to the pseudostationary phase. This difference in binding affinities is what leads to enantiomeric separation. Due to the very large number of possible chiral selectors, the development of a predictive model would be of significant benefit to separations scientists.<br/>This investigation is part of a long-term project aimed at developing a predictive Quantitative Structure-Enantioselective Retentions Relationship (QSERR) database for AABMMs. In this study, the chiral separation mechanisms of Dansyl amino acids, including Dansyl-Leucine, Dansyl-Norleucine, Dansyl-Tryptophan and Dansyl-Phenylalanine binding to poly sodium undecyl Leucine-Valine (SULV) were investigated using molecular dynamics simulation studies.

Chiral recognition of dansyl-derivatives by amino acid-based molecular micelles using molecular dynamics simulations

ACS Spring Meeting 2021

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