State Key Laboratory of High-efficiency Utilization of Coal and Green Chemical Engineering, College of Chemistry and Chemical Engineering, Ningxia University, Yinchuan, 750021, China.
State Key Laboratory of High-efficiency Utilization of Coal and Green Chemical Engineering, College of Chemistry and Chemical Engineering, Ningxia University, Yinchuan, 750021, China.
J Chromatogr A. 2024 Sep 27;1733:465228. doi: 10.1016/j.chroma.2024.465228. Epub 2024 Aug 7.
In this study, using chiral L-lysine as the molecular skeleton, three kinds of L-lysine-derived gelators (G, G and G) were synthesized and then bonded to the surface of silica matrix (5 μm) by amide condensation to prepare a series of multifunctional chromatography stationary phases (G-SiO, G-SiO, and G-SiO were prepared. The L-lysine-derived gelators not only possess chiral recognition ability, but also can spontaneously form oriented and ordered network structures in liquid medium through the interaction of non-covalent bonding forces such as hydrogen bonding, π-π stacking, and van der Waals forces. The comprehensive effect of multiple weak interaction sites enhances the molecular recognition ability and further improves the separation diversity of different types of compounds on stationary phases. The separation and evaluation of chiral compounds showed that benzoin, 1-phenyl-ethanol, 1-phenyl-propanol and 6-hydroxyflavanone could be separated in normal phase mode (NPLC). The separation of different types of non-chiral compounds, such as sulfonamides, nucleosides, nucleobases, polycyclic aromatic hydrocarbons (PAHs), anilines, and aromatic acids, were achieved in hydrophilic interaction/reversed-phase/ion-exchange mode (HILIC/RPLC/IEC), and the separation of polarized compounds could be performed under the condition of ultrapure water as the mobile phase, which has the typical retention characteristics of per aqueous liquid chromatography (PALC). The effects of organic solvent content, temperature, pH value, and buffer salt concentration on the retention and separation performance of the column were investigated. Comparison of the three prepared columns showed that the separation performance (such as aromatic selectivity) could be improved by increasing the types of functional groups on the surface of the stationary phase and the number of aromatic groups. In a word, the prepared stationary phase have multiple retention properties, can simultaneously separate chiral compounds and various types of achiral compounds. This work provides an idea for developing multifunctional liquid chromatography stationary phase materials, and further expands the application of gelators in separation science.
在这项研究中，我们使用手性 L-赖氨酸作为分子骨架，合成了三种 L-赖氨酸衍生的凝胶剂（G、G 和 G），然后通过酰胺缩合将其键合到硅基质表面（5 μm）上，制备了一系列多功能色谱固定相（G-SiO、G-SiO 和 G-SiO。L-赖氨酸衍生的凝胶剂不仅具有手性识别能力，而且可以通过氢键、π-π堆积和范德华力等非共价键相互作用在液相中自发形成定向和有序的网络结构。多个弱相互作用位点的综合效应增强了分子识别能力，进一步提高了不同类型化合物在固定相上的分离多样性。手性化合物的分离和评价表明，安息香、1-苯乙醇、1-苯丙醇和 6-羟基黄酮可以在正相模式（NPLC）下分离。不同类型的非手性化合物，如磺胺类、核苷、碱基、多环芳烃（PAHs）、苯胺和芳香酸，可以在亲水相互作用/反相/离子交换模式（HILIC/RPLC/IEC）下分离，在以超纯水为流动相的条件下可以进行极性化合物的分离，具有典型的反相高效液相色谱（PALC）保留特性。考察了有机溶剂含量、温度、pH 值和缓冲盐浓度对柱保留和分离性能的影响。对三种制备的色谱柱进行比较，结果表明，通过增加固定相表面的官能团类型和芳环数量，可以提高分离性能（如芳香选择性）。总之，所制备的固定相具有多种保留性质，可同时分离手性化合物和各种类型的非手性化合物。本工作为开发多功能液相色谱固定相材料提供了思路，并进一步拓展了凝胶剂在分离科学中的应用。
