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'One-pot' click access to triazole bridged cyclodextrin chiral phases for differentiation of clopidogrel enantiomers

机译:“一锅法”点击进入三唑桥连的环糊精手性相,用于区分氯吡格雷对映体

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The current work demonstrates a "one-pot" click synthetic procedure for the preparation of triazole bridged cyclodextrin (CD) chiral stationary phases (CSPs) and their application for efficient chiral differentiation of clopidogrel enantiomers under reversed-phase high performance liquid chromatography (HPLC). It was found that native-CD-CSPs and methylated-CD-CSPs showed good enantioselectivity towards clopidogrel enantiomers with acetonitrile (ACN)/water and methanol (MeOH)/water as mobile phases, respectively, while the more versatile phenylcarbamoylated-CD-CSP cannot resolve the enantiomers due to the steric hindrance of bulky phenylcarbamate moieties. Solvent selection plays an important role in CSP chiral recognition ability towards clopidogrel enantiomers. 6-Hydroxyl moieties on CD rims were found to participate in the chiral recognition process. The optimal chiral resolution (R-s) was improved to 1.95 by transferring the separation from 5 mu m native-CD-CSPs to 3 mu m native-CD-CSPs with ACN/buffer as the mobile phase.
机译:当前的工作演示了制备三唑桥联的环糊精(CD)手性固定相(CSP)的“一锅法”点击合成程序,以及它们在反相高效液相色谱(HPLC)下对氯吡格雷对映体进行有效的手性分化中的应用。发现天然CD-CSPs和甲基化CD-CSPs对氯吡格雷对映异构体分别以乙腈(ACN)/水和甲醇(MeOH)/水为流动相表现出良好的对映选择性,而更通用的苯基氨基甲酰化CD-CSP由于庞大的氨基甲酸苯基酯部分的空间位阻,因此不能拆分对映异构体。溶剂选择在CSP对氯吡格雷对映体的手性识别能力中起着重要作用。发现CD边缘上的6-羟基部分参与手性识别过程。通过以ACN /缓冲液为流动相,将5μm天然CD-CSPs的分离转移到3μm天然CD-CSPs,将最佳手性拆分度(R-s)提高到1.95。

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