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

作　　者：Mauro Garcia Nathan Black Eugene Billiot Fereshteh Billiot Kevin F. Morris Yayin Fang Mauro Garcia;Nathan Black;Eugene Billiot;Fereshteh Billiot;Kevin F. Morris;Yayin Fang(Department of Physical and Environmental Sciences, Texas A&M University-Corpus Christi, Corpus Christi, TX, USA;Department of Chemistry, Carthage College, Kenosha, WI, USA;Department of Biochemistry and Molecular Biology, Howard University, Washington, DC, USA)

机构地区：[1]Department of Physical and Environmental Sciences, Texas A&M University-Corpus Christi, Corpus Christi, TX, USA [2]Department of Chemistry, Carthage College, Kenosha, WI, USA [3]Department of Biochemistry and Molecular Biology, Howard University, Washington, DC, USA

出　　处：《Open Journal of Physical Chemistry》2021年第2期64-86,共23页物理化学期刊（英文）

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 </span><span style="font-family:Verdana;"><i></span><i><span style="font-family:Verdana;">N</span></i><i><span style="font-family:Verdana;"></i></span></i><span style="font-family:Verdana;">-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 </span><span style="font-family:Verdana;">-</span><span style="font-family:Verdana;">21.8938, </span><span style="font-family:Verdana;">-</span><span style="font-family:Verdana;">22.1763, </span><span style="font-family:Verdana;">-</span><span style="font-family:""><span style="font-family:Verdana;">21.3329 </span><span style="font-family:Verdana;">and </span></span><span style="font-family:Verdana;">-</span><span style="font-family:Verdana;">13.3349 kJ</span><span style="font-family:Verdana;">&middot;</span><span style="font-family:Verdana;">mol</span>^{<span style="font-family:Verdana;">-</span>}^{<span style="font-family:Verdana;">1</span>}<span style="font-family:Verdana;">, respectively. The D-enantiomers of Dans-Leu, Dans-Nor</span><span style="font-family:Verdana;">, DansIn 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 </span><span style="font-family:Verdana;"><i></span><i><span style="font-family:Verdana;">N</span></i><i><span style="font-family:Verdana;"></i></span></i><span style="font-family:Verdana;">-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 </span><span style="font-family:Verdana;">-</span><span style="font-family:Verdana;">21.8938, </span><span style="font-family:Verdana;">-</span><span style="font-family:Verdana;">22.1763, </span><span style="font-family:Verdana;">-</span><span style="font-family:""><span style="font-family:Verdana;">21.3329 </span><span style="font-family:Verdana;">and </span></span><span style="font-family:Verdana;">-</span><span style="font-family:Verdana;">13.3349 kJ</span><span style="font-family:Verdana;">&middot;</span><span style="font-family:Verdana;">mol</span>^{<span style="font-family:Verdana;">-</span>}^{<span style="font-family:Verdana;">1</span>}<span style="font-family:Verdana;">, respectively. The D-enantiomers of Dans-Leu, Dans-Nor</span><span style="font-family:Verdana;">, Dans

关 键 词：Amino Acid Based Molecular Micelles Molecular Modeling Computational Chemistry Chiral Recognition 

分 类 号：O62[理学—有机化学]