Use of Sulfated Cyclofructan 6 and Sulfated Cyclodextrins for the Chiral Separation of Four Basic Pharmaceuticals by Capillary Electrophoresis

Zhang, Yi Jun; Huang, Ming Xian; Zhang, Yu Ping; Armstrong, Daniel W.; Breitbach, Zachary S.; Ryoo, Jae Jeong

doi:10.1002/chir.22206

Cited by 26 publications

(20 citation statements)

References 34 publications

(70 reference statements)

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“…They have, over the years, been proposed as novel selective complex‐forming agent for metal cations and as CSPs and CSs in HPLC, GC, and CE . Native CFs did not demonstrate any significant enantioselectivity, while several CF derivatives have been successfully used as CSs in CE . It was also reported that the enantioselective behavior of CFs is different from that of CDs .…”

Section: Chiral Selectorsmentioning

confidence: 99%

Chiral selectors in CE: Recent development and applications (mid‐2014 to mid‐2016)

Stavrou

Agathokleous

Kapnissi‐Christodoulou

2017

Electrophoresis

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This report, which is a sequence of a series of reviews, records the most important chiral selectors (CSs) applied in CE. It highlights the CSs that were used during the period 2014 to mid-2016. In this review, method developments, validations, and pharmaceutical along with biomedical applications are presented. The different CSs include CDs, antibiotics, cyclofructants, linear and branched oligo- and polysaccharides, and polymeric surfactants. In addition, the advantages of these CSs, along with their chiral recognition mechanisms, and their performance, are discussed.

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Section: Chiral Selectorsmentioning

confidence: 99%

Chiral selectors in CE: Recent development and applications (mid‐2014 to mid‐2016)

Stavrou

Agathokleous

Kapnissi‐Christodoulou

2017

Electrophoresis

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“…For example, the enantiomeric separation of ruthenium polypyridyl complexes has been obtained with macrocyclic glycopeptide CSPs and cyclodextrin (CD) CSPs. 30 The R-naphthylethyl functionalized CF6 CSP proved more suitable for the enantiomeric separation of binaphthyl catalysts when compared to the R-naphthylethyl functionalized CD CSP. They are naturally occurring chiral crown ethers which consist of β-(2-1) linked D-fructofuranose units.…”

Section: Introductionmentioning

confidence: 95%

Enantiomeric Separations of Ruthenium (II) Polypyridyl Complexes Using HPLC With Cyclofructan Chiral Stationary Phases

et al. 2014

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The enantiomeric separation of 21 ruthenium (II) polypyridyl complexes was achieved with a novel class of cyclofructan-based chiral stationary phases (CSPs) in the polar organic mode. Aromatic derivatives on the chiral selectors proved to be essential for enantioselectivity. The R-napthylethyl carbamate functionalized cyclofructan 6 (LARIHC CF6-RN) column proved to be the most effective overall, while the dimethylphenyl carbamate cyclofructan 7 (LARIHC CF7-DMP) showed complementary selectivity. A combination of acid and base additives was necessary for optimal separations. The retention factor vs. acetonitrile/methanol ratio plot showed a U-shaped retention curve, indicating that different interactions take place at different polar organic solvent compositions. The separation results indicated that π-π interactions, steric effects, and hydrogen bonding contribute to the enantiomeric separation of ruthenium (II) polypyridyl complexes with cyclofructan chiral stationary phases in the polar organic mode.

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“…The type of the substituent and the degree of substitution have proven to be a determining step in enantiorecognition . On the other hand, the utilization of CFs and their derivatives as CSs in CE is limited, and this is demonstrated by the low number of publications . Native CFs did not demonstrate any significant enantioselectivity, while their derivatives have successfully been applied as CSs in CE .…”

Section: Introductionmentioning

confidence: 99%

Synergistic enantioseparation systems with either cyclodextrins or cyclofructans and L‐alanineTertbutyl ester lactate

et al. 2018

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The combined use of chiral ionic liquids (CILs) and conventional chiral selectors (CSs) in CE, to establish a synergistic system, has proven to be an effective approach for the separation of enantiomeric pairs. In this study, a new CE method was developed, employing a binary system of a CS, either a cyclodextrin (CD) or a cyclofructan (CF), and a chiral amino acid ester‐based ionic liquid (AAIL), for the chiral separation of four basic, acidic and zwitterionic drug compounds. In particular, the enantioseparation of two anticoagulants, warfarin (WAR) and coumachlor (COU), a non‐opioid analgesic, nefopam (NEF) and a third‐generation antihistamine, fexofenadine (FXD), was examined, by supporting the BGE with a CS and the chiral AAIL L‐alanine tert butyl ester lactate (L‐AlaC4Lac). Parameters, such as the type of the CS, the concentration of both the CS and L‐AlaC4Lac, and the BGE pH, were methodically examined in order to optimize the chiral separation of each analyte. It was observed that, in some cases, the addition of the AAIL into the BGE improved both resolution (Rs) and efficiency (N) significantly. In other cases, the synergistic effect enabled baseline separation of analyte enantiomers, at a much lower concentration of the CS. Finally, after optimization of separation conditions, baseline separations (Rs>1.5) of all four analytes were achieved in less than 5 min.

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Use of Sulfated Cyclofructan 6 and Sulfated Cyclodextrins for the Chiral Separation of Four Basic Pharmaceuticals by Capillary Electrophoresis

Cited by 26 publications

References 34 publications

Chiral selectors in CE: Recent development and applications (mid‐2014 to mid‐2016)

Chiral selectors in CE: Recent development and applications (mid‐2014 to mid‐2016)

Enantiomeric Separations of Ruthenium (II) Polypyridyl Complexes Using HPLC With Cyclofructan Chiral Stationary Phases

Synergistic enantioseparation systems with either cyclodextrins or cyclofructans and L‐alanineTertbutyl ester lactate

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