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Novel chiral stationary phases based on 3,5-dimethyl phenylcarbamoylated β-cyclodextrin combining cinchona alkaloid moiety.
Chirality ( IF 2.8 ) Pub Date : 2020-05-08 , DOI: 10.1002/chir.23237
Lunan Zhu 1 , Junchen Zhu 1 , Xiaotong Sun 1 , Yaling Wu 1 , Huiying Wang 1 , Lingping Cheng 1 , Jiawei Shen 1 , Yanxiong Ke 1
Affiliation  

Novel chiral selectors based on 3,5‐dimethyl phenylcarbamoylated β‐cyclodextrin connecting quinine (QN) or quinidine (QD) moiety were synthesized and immobilized on silica gel. Their chromatographic performances were investigated by comparing to the 3,5‐dimethyl phenylcarbamoylated β‐cyclodextrin (β‐CD) chiral stationary phase (CSP) and 9‐O‐(tert‐butylcarbamoyl)‐QN‐based CSP (QN‐AX). Fmoc‐protected amino acids, chiral drug cloprostenol (which has been successfully employed in veterinary medicine), and neutral chiral analytes were evaluated on CSPs, and the results showed that the novel CSPs characterized as both enantioseparation capabilities of CD‐based CSP and QN/QD‐based CSPs have broader application range than β‐CD‐based CSP or QN/QD‐based CSPs. It was found that QN/QD moieties play a dominant role in the overall enantioseparation process of Fmoc‐amino acids accompanied by the synergistic effect of β‐CD moiety, which lead to the different enantioseparation of β‐CD‐QN‐based CSP and β‐CD‐QD‐based CSP. Furthermore, new CSPs retain extraordinary enantioseparation of cyclodextrin‐based CSP for some neutral analytes on normal phase and even exhibit better enantioseparation than the corresponding β‐CD‐based CSP for certain samples.

中文翻译:

基于3,5-二甲基苯基氨基甲酰基化的β-环糊精结合金鸡纳生物碱部分的新型手性固定相。

合成了基于3,5-二甲基苯基氨基甲酰基化的β-环糊精连接奎宁(QN)或奎尼丁(QD)部分的新型手性选择剂,并将其固定在硅胶上。通过与3,5-二甲基苯基氨基甲酰基化的β-环糊精(β-CD)手性固定相(CSP)和9- O-)进行比较,研究了它们的色谱性能。-丁基氨基甲酰基)-基于QN的CSP(QN-AX)。在CSP上评估了Fmoc保护的氨基酸,手性药物Cloprostenol(已成功用于兽医学)和中性手性分析物,结果表明,这种新型CSP既具有CD基CSP的对映体分离能力,又具有QN /与基于β-CD的CSP或基于QN / QD的CSP相比,基于QD的CSP具有更广泛的应用范围。发现QN / QD部分在Fmoc-氨基酸的整个对映体分离过程中起主导作用,并伴随有β-CD部分的协同作用,从而导致基于β-CD-QN的CSP和β的不同对映体分离基于CD-QD的CSP。此外,
更新日期:2020-05-08
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