Chiral Recognition of Dansyl Derivatives with an Amino Acid-Based Molecular Micelle: A Molecular Dynamics Investigation.
Chiral Recognition of Dansyl Derivatives with an Amino Acid-Based Molecular Micelle: A Molecular Dynamics Investigation.
复制标题
DOI：
10.4236/ojpc.2021.112004
复制
发表时间：
2021-05
期刊：
影响因子：
--
通讯作者：
Fang Y
中科院分区：
文献类型：
--
作者：
Mauro G;Black N;Billiot E;Billiot F;Morris KF;Fang Y
本研究采用分子动力学模拟方法研究了丹酰氨基酸（包括丹酰亮氨酸（Dans-Leu）、丹酰正亮氨酸（Dans-Nor）、丹酰色氨酸（Dans-Trp）和丹酰苯丙氨酸（Dans-Phe））与聚N-十一酰-（L）-亮氨酰缬氨酸钠（poly（SULV））结合的手性拆分机理。胶束电动色谱法（MEKC）先前已经表明，当分离这些前述丹磺酰氨基酸的对映体时，L-对映体比D-对映体更强地结合聚（SULV）。本研究的目的是利用计算方法研究这些体系中控制手性识别的分子间相互作用。这项研究表明，计算计算的结合自由能值丹磺酰对映体结合聚（SULV）是在实验MEKC研究中产生的对映体顺序一致。Dans-Leu、Dans-Nor、Dans-Trp和Dans-Phe的L-对映异构体与poly（SULV）中它们优选的结合口袋结合，产生的结合自由能值分别为−21.8938、−22.1763、−21.3329和−13.3349 kJ·mol−1。Dans-Leu、Dans-Nor、Dans-Trp和Dans-Phe的D-对映异构体与poly（SULV）中它们优选的结合口袋结合，产生的结合自由能值分别为−14.5811、−15.9457、−13.6408和−12.0959 kJ·mol−1。此外，氢键分析被用来调查和阐明的分子相互作用，在这些分子系统中的手性识别。
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 −12.0959 kJ·mol−1, respectively. Furthermore, hydrogen bonding analyses were used to investigate and elucidate the molecular interactions that govern chiral recognition in these molecular systems.