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橙皮素硫脲衍生物在直链淀粉和纤维素聚合物手性色谱柱上的对映体分离。

Enantiomeric separation of thiourea derivatives of naringenin on amylose and cellulose polymeric chromatographic chiral columns.

机构信息

Department of Chemistry, Jamia Millia Islamia (Central University), New Delhi, India.

Bioactive Molecules and Chiral Separation Laboratory, Faculty of Exact Sciences, Tahri Mohammed's University, Béchar, Algeria.

出版信息

Chirality. 2024 Mar;36(3):e23659. doi: 10.1002/chir.23659.

Abstract

Due to a great demand for amylose and cellulose polymeric chromatographic chiral columns, the enantiomeric separation of thiourea derivatives of naringenin was achieved on the different amylose (Chiralpak-IB) and cellulose chiral (Chiralcel-OJ and Chiralcel-OD-3R) columns with varied chromatographic conditions. The isocratic mobile phases used were ethanol and methanol, where ethanol/hexane and methanol/hexane were used as gradient mode and were prepared in volume/volume relation. The separation and resolution factors for all the enantiomers were in the range of 1.25 to 3.47 and 0.48 to 1.75, respectively. The enantiomeric resolution was obtained within 12 min making fast separation. The docking studies confirmed the chiral recognition mechanisms with binding affinities in the range of -4.7 to -5.7 kcal/mol. The reported compounds have good anticoagulant activities and may be used as anticoagulants in the future. Besides, chiral separation is fast and is useful for enantiomeric separation in any laboratory in the world.

摘要

由于对直链淀粉和纤维素聚合物色谱手性柱的巨大需求,橙皮素硫脲衍生物的对映体分离在不同的直链淀粉(Chiralpak-IB)和纤维素手性(Chiralcel-OJ 和 Chiralcel-OD-3R)柱上,通过不同的色谱条件得以实现。使用的等度流动相为乙醇和甲醇,其中乙醇/己烷和甲醇/己烷作为梯度模式,按体积/体积关系制备。所有对映体的分离和分辨率因子分别在 1.25 到 3.47 和 0.48 到 1.75 之间。对映体的分辨率在 12 分钟内即可获得,实现了快速分离。对接研究证实了手性识别机制,结合亲和力在-4.7 到-5.7 kcal/mol 之间。所报道的化合物具有良好的抗凝活性,将来可能用作抗凝剂。此外,手性分离速度快,在手性分离方面在世界上任何实验室都很有用。

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