Chiral Recognition of Dansyl Derivatives with an Amino Acid-Based Molecular Micelle: A Molecular Dynamics Investigation

摘要

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, - style="font-family:""> style="font-family:Verdana;">21.3329 style="font-family:Verdana;">and style="font-family:Verdana;">- style="font-family:Verdana;">13.3349 kJ style="font-family:Verdana;">· style="font-family:Verdana;">mol style="font-family:Verdana;">- style="font-family:Verdana;">1 style="font-family:Verdana;">, respectively. The D-enantiomers of Dans-Leu, Dans-Nor style="font-family:Verdana;">, Dans-Trp, and Dans-Phe binding to their preferred binding pockets in poly (SULV) yielded binding free energy values of style="font-family:Verdana;">- style="font-family:Verdana;">14.5811, style="font-family:Verdana;">- style="font-family:Verdana;">15.9457, style="font-family:Verdana;">- style="font-family:Verdana;">13.6408, and style="font-family:Verdana;">- style="font-family:""> style="font-family:Verdana;">12.0959 style="font-family:Verdana;">kJ style="font-family:Verdana;">· style="font-family:Verdana;">mol style="font-family:Verdana;">- style="font-family:Verdana;">1 style="font-family:Verdana;">, respectively. Furthermore, hydrogen bonding analyses w style="font-family:Verdana;">ere style="font-family:Verdana;"> used to investigate and elucidate the molecular interactions that govern chiral recognition in these molecular systems.