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奥美拉唑及其手性杂质B和E在直链淀粉三（3-氯-5-甲基苯基氨基甲酸酯）手性固定相上在极性有机模式下的异常保留行为。

Unusual retention behavior of omeprazole and its chiral impurities B and E on the amylose tris (3-chloro-5-methylphenylcarbamate) chiral stationary phase in polar organic mode.

作者信息

Ferretti Rosella, Zanitti Leo, Casulli Adriano, Cirilli Roberto

机构信息

Centro nazionale per il controllo e la valutazione dei farmaci, Istituto Superiore di Sanità, Viale Regina Elena 299, 00161 Rome, Italy.

European Union Reference Laboratory for the Parasites, Istituto Superiore di Sanità, Viale Regina Elena 299, 00161 Rome, Italy.

出版信息

J Pharm Anal. 2018 Aug;8(4):234-239. doi: 10.1016/j.jpha.2018.04.001. Epub 2018 Apr 20.

DOI:10.1016/j.jpha.2018.04.001
PMID:30140487
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6104149/
Abstract

Recent reports have demonstrated that the new commercially available immobilized-type chiral stationary phases (CSPs) containing amylose tris(3-chloro-5-methylphenylcarbamate) (ACMPC) as a selector exhibit not only an exceptionally high enantioselectivity in high-performance liquid chromatography (HPLC) but they are also applicable to a wide range of chiral analytes. Herein, we report the results obtained in the HPLC analysis of omeprazole and its impurities B and E on the ACMPC-based Chiralpak IG-3 CSP (CSP) under polar organic conditions. A systematic evaluation of the retention characteristics of the selected benzimidazole chiral probes was carried out by changing the composition of the mobile phase and the column temperature. It is worth emphasizing that the high affinity of both enantiomers of all analytes recorded in pure methanol mode dramatically decreased incorporating small volumes of either basic or acid additives in the mobile phase. Unspecified sites of the IG-3 CSP presumably involved in strong and non-stereoselective H-bonding contacts with chiral analytes are assumed responsible for the unproductive retention process.

摘要

最近的报道表明，新型市售的以直链淀粉三（3-氯-5-甲基苯基氨基甲酸酯）（ACMPC）为选择剂的固定化手性固定相（CSPs）不仅在高效液相色谱（HPLC）中表现出极高的对映体选择性，而且还适用于多种手性分析物。在此，我们报告了在极性有机条件下，在基于ACMPC的Chiralpak IG-3 CSP（CSP）上对奥美拉唑及其杂质B和E进行HPLC分析所获得的结果。通过改变流动相的组成和柱温，对所选苯并咪唑手性探针的保留特性进行了系统评估。值得强调的是，在纯甲醇模式下记录的所有分析物的两种对映体的高亲和力，在流动相中加入少量碱性或酸性添加剂后显著降低。推测IG-3 CSP的未指定位点与手性分析物发生了强烈的非立体选择性氢键接触，这被认为是导致非生产性保留过程的原因。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/19d2/6104149/775ab5896abf/gr7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/19d2/6104149/99db90db5efc/gr1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/19d2/6104149/00b9cb52ec8a/gr2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/19d2/6104149/6e27dd6d3d1b/gr3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/19d2/6104149/eb0eca6411ea/gr4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/19d2/6104149/e4579c8c0e97/gr5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/19d2/6104149/c5ace39b4534/gr6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/19d2/6104149/775ab5896abf/gr7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/19d2/6104149/99db90db5efc/gr1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/19d2/6104149/00b9cb52ec8a/gr2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/19d2/6104149/6e27dd6d3d1b/gr3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/19d2/6104149/eb0eca6411ea/gr4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/19d2/6104149/e4579c8c0e97/gr5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/19d2/6104149/c5ace39b4534/gr6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/19d2/6104149/775ab5896abf/gr7.jpg

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