Chiral drug enantiomers often have different physiological properties. Racemates are, therefore, separated into their enantiopure forms so the properties of the enantiomers can be studied separately. In capillary electrophoresis, enantiomers can be separated based upon their interactions with chiral molecular micelles. A molecular micelle is a macromolecule made up of covalently bound surfactant monomers. The goal of this project was to use molecular modeling to characterize how the enantiomers of chiral drugs interact with molecular micelles. The molecular micelle poly-(sodium undecyl-(L,L)-leucine-leucine) (poly(SULL)) was investigated along with the chiral molecules oxprenolol, propranolol, 1,1’-bi-2-naphthol, and lorazepam. The enantiomers of each molecule were first docked into poly(SULL) binding pockets. Molecular dynamics simulations were then used to calculate the solvent accessible surface areas of each ligand, the hydrogen bonds formed between the ligand and molecular micelle, and each ligand’s molecular micelle binding free energy. These results were used to gain insight into the mechanism of chiral recognition by poly(SULL) and similar molecular micelles.

Molecular dynamics simulation study of chiral recognition by dipeptide-based molecular micelles

253rd National Meeting (2017)

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