Hellinghausen Garrett, Lopez Diego A, Lee Jauh T, Wang Yadi, Weatherly Choyce A, Portillo Abiud E, Berthod Alain, Armstrong Daniel W
Department of Chemistry and Biochemistry, The University of Texas at Arlington, Arlington, Texas, USA.
AZYP, LLC, Arlington, Texas, USA.
Chirality. 2018 Sep;30(9):1067-1078. doi: 10.1002/chir.22985. Epub 2018 Jul 3.
A modified macrocyclic glycopeptide-based chiral stationary phase (CSP), prepared via Edman degradation of vancomycin, was evaluated as a chiral selector for the first time. Its applicability was compared with other macrocyclic glycopeptide-based CSPs: TeicoShell and VancoShell. In addition, another modified macrocyclic glycopeptide-based CSP, NicoShell, was further examined. Initial evaluation was focused on the complementary behavior with these glycopeptides. A screening procedure was used based on previous work for the enantiomeric separation of 50 chiral compounds including amino acids, pesticides, stimulants, and a variety of pharmaceuticals. Fast and efficient chiral separations resulted by using superficially porous (core-shell) particle supports. Overall, the vancomycin Edman degradation product (EDP) resembled TeicoShell with high enantioselectivity for acidic compounds in the polar ionic mode. The simultaneous enantiomeric separation of 5 racemic profens using liquid chromatography-mass spectrometry with EDP was performed in approximately 3 minutes. Other highlights include simultaneous liquid chromatography separations of rac-amphetamine and rac-methamphetamine with VancoShell, rac-pseudoephedrine and rac-ephedrine with NicoShell, and rac-dichlorprop and rac-haloxyfop with TeicoShell.
通过对万古霉素进行埃德曼降解制备的一种基于大环糖肽的改性手性固定相（CSP）首次被评估为一种手性选择剂。将其适用性与其他基于大环糖肽的CSP：TeicoShell和VancoShell进行了比较。此外，还对另一种基于大环糖肽的改性CSP，即NicoShell进行了进一步研究。初步评估集中在与这些糖肽的互补行为上。基于先前用于对包括氨基酸、农药、兴奋剂和多种药物在内的50种手性化合物进行对映体分离的工作，采用了一种筛选程序。使用表面多孔（核壳）颗粒载体实现了快速高效的手性分离。总体而言，万古霉素埃德曼降解产物（EDP）在极性离子模式下对酸性化合物具有高对映选择性，类似于TeicoShell。使用EDP通过液相色谱 - 质谱联用对5种外消旋布洛芬进行对映体同时分离在大约3分钟内完成。其他亮点包括使用VancoShell对rac - 苯丙胺和rac - 甲基苯丙胺进行液相色谱同时分离，使用NicoShell对rac - 伪麻黄碱和rac - 麻黄碱进行分离，以及使用TeicoShell对rac - 二氯丙酸和rac - 氯氟吡氧乙酸进行分离。
