Enantioseparation of phenethylamines by using high-performance liquid chromatography column permanently coated with methylated β-cyclodextrin.

Published on Jun 2, 2021in Journal of Separation Science2.878
· DOI :10.1002/JSSC.202100343
Hiroyuki Terashima4
Estimated H-index: 4
Atsushi Yamamoto19
Estimated H-index: 19
(Chubu University)
+ 4 AuthorsShuji Kodama18
Estimated H-index: 18
(Tokai University)
Cyclodextrins and their derivatives have been used for chiral HPLC selectors, while they are costly to use as mobile phase additives in HPLC. Here, we report application of phenyl column coated permanently with methylated β-cyclodextrin for chiral HPLC. A 0.1% (v/v) phosphoric acid solution containing 1 M NaCl and 0.5% (w/v) methylated β-cyclodextrin was subjected to a phenyl column at a flow rate of 0.5 mL/min at 30 °C for 2 h. Using the precoating phenyl column, all the enantiomers of the four phenethylamines (norepinephrine, epinephrine, octopamine, and synephrine) were successfully separated simultaneously by HPLC with a mobile phase without methylated β-cyclodextrin at a flow rate of 0.2 mL/min at 30 °C. The enantioseparation ability was retained for successive analyses during one week. It is suggested that inclusion complex of methylated β-cyclodextrin with a phenyl group on the surface of the stationary phase could be formed and that the inclusion complex could form the ternary complex with the injected analytes. The longer retention time of (S)-enantiomers of analytes than corresponding (R)-enantiomers for HPLC could be explained from the higher stability of the methylated β-cyclodextrin complexes with (S)-enantiomers, which were confirmed by CE and 1 H nuclear magnetic resonance experiments. This article is protected by copyright. All rights reserved.
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