Sugammadex, Subetadex and Sualphadex as chiral selectors

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The present contribution describes for the first time the application of three single-isomeric cyclodextrin derivatives – Sugammadex, Subetadex and Sualphadex as chiral selectors. Their recognition ability was investigated by means of chiral capillary electrophoresis, on a pool of cathinone and amphetamine derivatives. The selectors differ in cavity sizes and in the number of ionizable groups which evidently influenced their enantioselectivity performance. Their common feature is their high isomeric purity which enabled the detailed study of the molecular association between the cathinone guest and the cyclodextrin host at the atomic level. With the aid of enantiopure cathinone derivatives, the migration order could be also determined in capillary electrophoresis. As the result of the capillary electrophoresis screening, partial or baseline chiral separation of 19 cathinones and an amphetamine derivative could be achieved and the systematic study was performed focusing on three different pH conditions pH = 7.0, pH = 5.0 and pH = 2.5 and several different selector concentrations. Among the tested derivatives Subetadex is the best performing chiral selector, especially under acidic pH values for separating enantiomers, proven not only by capillary electrophoresis but also by 1D and 2D NMR measurements.

Dóra Ujj, Eszter Kalydi, Milo Malanga, Erzsébet Varga, Tamás Sohajda, Szabolcs Béni, Gábor Benkovics (2022) Sugammadex analogue cyclodextrins as chiral selectors for enantioseparation of cathinone derivatives by capillary electrophoresis. Journal of Chromatography A 463506.

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