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J Chromatogr A. 2014 Aug 15;1355:291-5. doi: 10.1016/j.chroma.2014.06.022. Epub 2014 Jun 12.

High-performance liquid chromatographic enantioseparation of 3,5-disubstituted hydantoins analogs and temperature-induced reversals of elution orders on a polysaccharide-based chiral stationary phase.

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  • 1School of Pharmacy, Shandong University, Ji'nan 250012, China.
  • 2School of Pharmacy, Shandong University, Ji'nan 250012, China; Department of Chemistry and Center for Diagnostics and Therapeutics, Georgia State University, Atlanta, GA 30303, USA.
  • 3School of Pharmacy, Shandong University, Ji'nan 250012, China. Electronic address: haofangcn@sdu.edu.cn.

Abstract

Enantioseparations were achieved for eleven 3,5-disubstituted hydantoins in HPLC under the normal phase mode using Chiralpak IA. The effects of polar alcoholic modifier and column temperature on retention and enantioseparation were determined. Importantly, we found two kinds of enantiomer elution order (EEO) reversals, which include solvent-induced EEO reversal for compound 9 and temperature-induced EEO reversals for compound 3 and compound 6. The phenomena of these EEO reversals were described for the first time in present work, which is helpful to elucidate the chiral separation mechanism of these hydantoins.

Copyright © 2014 Elsevier B.V. All rights reserved.

KEYWORDS:

3,5-Disubstituted hydantoins; Chrialpak IA column; Enantiomer separation; Reversal of elution order

[PubMed - indexed for MEDLINE]
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