In this study, the chiral separation mechanisms of Dansyl amino acids,
including Dansyl-Leucine (Dans-Leu), Dansyl-Norleucine (Dans-Nor), Dansyl-Tryptophan
(Dans-Trp) and Dansyl-Phenylalanine (Dans-Phe) binding to poly-sodium N-undecanoyl-(L)-Leucylvalinate,
poly (SULV), were investigated using molecular dynamics simulations. Micellar
electrokinetic chromatography (MEKC) has previously shown that when separating
the enantiomers of these aforementioned Dansyl amino acids, the L-enantiomers bind
stronger to poly (SULV) than the D-enantiomers. This study aims to investigate
the molecular interactions that govern chiral recognition in these systems
using computational methods. This study reveals that the
computationally-calculated binding free energy values for Dansyl enantiomers
binding to poly (SULV) are in agreement with the enantiomeric order produced in
experimental MEKC studies. The L-enantiomers of Dans-Leu, Dans-Nor, Dans-Trp,
and Dans-Phe binding to their preferred binding pockets in poly (SULV) yielded
binding free energy values of -21.8938, -22.1763, -21.3329 and -13.3349 kJ·mol-1, respectively. The D-enantiomers
of Dans-Leu, Dans-Nor, Dans-Trp, and Dans-Phe binding to their preferred
binding pockets in poly (SULV) yielded binding free energy values of -14.5811, -15.9457, -13.6408, and -
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