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)
Sources
Abstract
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.
📖 Papers frequently viewed together
32 Citations
33 Citations
20172.17Chirality
6 Authors (Xiaoyu Hu, ..., Xingjie Guo)
5 Citations
References40
Newest
#1Martin G. Schmid (University of Graz)H-Index: 36
#2Johannes S. Hägele (University of Graz)H-Index: 5
Abstract Novel Psychoactive Substances (NPS) represent an alternative to established illicit drugs. They are traded via the internet and exhibit small alterations in their chemical structure to circumvent law, however, their psychotropic effects are comparable. There is still poor knowledge about side effects and health risks. By the end of 2018, 730 NPS were reported to EMCDDA (European Monitoring Centre for Drugs and Drug Addiction). Among different compound classes, many NPS are chiral and fe...
10 CitationsSource
#1Renata ZátopkováH-Index: 1
#2Zeineb AturkiH-Index: 29
Last. Petr BednářH-Index: 17
view all 3 authors...
A nano-liquid chromatographic method for the stereoisomer separation of some flavanone aglycones and 7-O-glycosides has been proposed employing a C18 capillary column and a chiral mobile phase additive such as cyclodextrin. The chiral separation of eriodictyol, naringenin and hesperitin was obtained by addition of carboxymethyl-β-cyclodextrin to the mobile phase, whereas eriocitrin, naringin, narirutin and hesperidin diastereoisomers were resolved by using sulfobutyl ether-β-cyclodextrin. The in...
1 CitationsSource
#1Yuri Watanabe (Tokai University)H-Index: 1
#2Ikko Mikami (Tokai University)H-Index: 5
Last. Shuji Kodama (Tokai University)H-Index: 18
view all 8 authors...
Direct enantioseparation of mandelic acid by high-performance liquid chromatography (HPLC) with a reversed phase column and a mobile phase containing a small amount of hydroxylpropyl-beta-cyclodextrin (HP-beta-CD) was studied as an efficient method for saving consumption of the CD additive. As a result, it was proposed that racemic mandelic acid can be analyzed with a phenyl column by using a mobile phase composed of 10 mM ammonium acetate buffer (pH 4.2) and 0.02% (w/v) HP-beta-CD at a flow rat...
1 CitationsSource
#1Manisha Singh (LPU: Lovely Professional University)H-Index: 1
#2Sonika Sethi (GD Goenka University)H-Index: 2
Last. Ravi Bhushan (IITR: Indian Institute of Technology Roorkee)H-Index: 26
view all 3 authors...
: The control of enantiomeric purity and determination of individual enantiomeric drug molecules remains the subject of importance for clinical, analytical, and regulatory purposes and to facilitate an accurate evaluation of the risks posed by them to human health. A large number of pharmaceuticals are marketed and administered as racemates. Etodolac is among such nonsteroidal anti-inflammatory drugs. Overall literature reports on its enantioseparation are scanty. Liquid chromatography (LC) meth...
4 CitationsSource
#1Zehra Irem Yildiz (Bilkent University)H-Index: 13
#2Mehmet Emin Kilic (Bilkent University)H-Index: 9
Last. Tamer Uyar (Bilkent University)H-Index: 59
view all 4 authors...
The electrospinning nanofibers (NFs) of cinnamaldehyde inclusion complexes (ICs) with two different hydroxypropylated cyclodextrins (CDs), hydroxypropyl-β-cyclodextrin (HP-β-CD) and hydroxypropyl-γ-cyclodextrin (HP-γ-CD), was successfully performed in order to produce cinnamaldehyde/CD-IC NFs without using additional polymer matrix. The inclusion complexation between cinnamaldehyde and hydroxypropylated CDs was studied by computational molecular modeling and the results suggested that HP-β-CD an...
12 CitationsSource
#1Erzsébet VargaH-Index: 11
#2Gábor BenkovicsH-Index: 9
Last. Szabolcs Béni (Semmelweis University)H-Index: 25
view all 7 authors...
: The chiral separation ability of the full library of methylated-β-cyclodextrins towards pharmacologically significant racemic drugs including basic compounds was studied by chiral CE. The syntheses of all the methylated, single isomer β-cyclodextrins were revised and optimized and the aqueous solubility of the derivatives was unambiguously established. The three most relevant commercially available methylated isomeric mixtures were also included in the screening, so a total of ten various meth...
4 CitationsSource
#1Chiara FanaliH-Index: 29
#2Giovanni D'OrazioH-Index: 28
Last. Salvatore Fanali (University of Verona)H-Index: 62
view all 4 authors...
The separation of enantiomers has been started in the past and continues to be a topic of great interest in various fields of research, mainly because these compounds could be involved in biological processes such as, for example, those related to human health. Great attention has been devoted to studies for the analysis of enantiomers present in food products in order to assess authenticity and safety. The separation of these compounds can be carried out utilizing analytical techniques such as ...
10 CitationsSource
#1Joana Teixeira (University of Porto)H-Index: 9
#2Maria Elizabeth Tiritan (IPN: Instituto Politécnico Nacional)H-Index: 29
Last. Carla Fernandes (University of Porto)H-Index: 23
view all 4 authors...
The planning and development of new chiral stationary phases (CSPs) for liquid chromatography (LC) are considered as continuous and evolutionary issues since the introduction of the first CSP in 1938. The main objectives of the development strategies were to attempt the improvement of the chromatographic enantioresolution performance of the CSPs as well as enlarge their versatility and range of applications. Additionally, the transition to ultra-high-performance LC were underscored. The most rec...
28 CitationsSource
#1Federica Ianni (University of Perugia)H-Index: 16
#2Lucia Pucciarini (University of Perugia)H-Index: 6
Last. Benedetto Natalini (University of Perugia)H-Index: 23
view all 7 authors...
: Chiral ligand-exchange chromatography is one of the elective strategies for the direct enantioresolution of small chelating compounds: amino acids, diamines, amino alcohols, diols, small peptides, etc. Unlike other methods, the interaction between chiral selector and analyte enantiomers is mediated by a cation, thus producing diastereomeric ternary complexes. Two main approaches are conventionally applied in chiral ligand-exchange chromatography. The first relies upon chiral stationary phases ...
4 CitationsSource
#1Miriana Kfoury (Lebanese University)H-Index: 14
#2David Landy (CNRS: Centre national de la recherche scientifique)H-Index: 26
Last. Sophie Fourmentin (CNRS: Centre national de la recherche scientifique)H-Index: 33
view all 3 authors...
Cyclodextrins (CDs) are a family of cyclic oligosaccharides that constitute one of the most widely used molecular hosts in supramolecular chemistry. Encapsulation in the hydrophobic cavity of CDs positively affects the physical and chemical characteristics of the guests upon the formation of inclusion complexes. Such a property is interestingly employed to retain volatile guests and reduce their volatility. Within this scope, the starting crucial point for a suitable and careful characterization...
35 CitationsSource
Cited By0
Newest