Development of an improved ligand exchange chiral stationary phase based on leucinol for the resolution of proton pump inhibitors

Ha, Jin Joo; Han, Hye Jee; Kim, Hee Eun; Jin, Jong Sung; Jeong, Euh Duck; Hyun, Myung Ho

doi:10.1016/j.jpba.2014.07.029

Cited by 14 publications

(7 citation statements)

References 22 publications

(35 reference statements)

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“…(B) Exemplary chromatogram obtained for the chiral separation of rac ‐omeprazole in the following experimental conditions: mobile phase, 65% acetonitrile in water containing 0.5 mM CuSO 4 , 0.10 mM triethylamine and 0.05 mM acetic acid; eluent flow rate, 0.5 mL/min; column temperature, 20°C; detection wavelength, 254 nm UV. Adapted from …”

Section: B‐cspsmentioning

confidence: 99%

See 1 more Smart Citation

Last ten years (2008–2018) of chiral ligand‐exchange chromatography in HPLC: An updated review

Ianni

Pucciarini

Carotti

et al. 2018

J of Separation Science

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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 where the chiral selector is either covalently immobilized or physically adsorbed onto suitable packing materials (coated phases). In the second approach, chiral molecules are added to the eluent, thus generating chiral eluent systems. Among the advantages of chiral ligand-exchange chromatography, the generation of UV/vis-active metal complexes, and the use of commercially available or easy-to-synthesize chiral selectors, in combination to rather inexpensive achiral columns for coated phases and chiral eluents, are noteworthy. Besides amino acids and amino alcohols, other species have proven suitable for chiral ligand-exchange chromatography applications. Recently, the use of either chiral ionic liquids or micellar liquid chromatography systems as well as the successful off-column formation of diastereomeric complexes have expanded the selectivity profiles and application fields. All of these issues are touched in the review, shedding light to the contributions appeared in the last decade.

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Section: B‐cspsmentioning

confidence: 99%

“…A new B‐CSP based on a ( S )‐leucinol derivative as the chiral selector was developed by Hyun and co‐workers to improve the enantioresolution of PPIs. This phase was the stereochemical variant of the formerly synthesized one carrying a ( R )‐leucinol derivative as the enantiorecognition element (i.e., the chiral selector) .…”

Section: B‐cspsmentioning

confidence: 99%

Last ten years (2008–2018) of chiral ligand‐exchange chromatography in HPLC: An updated review

Ianni

Pucciarini

Carotti

et al. 2018

J of Separation Science

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“…During the last several decades, quite effective CSPs have been developed by utilizing various chiral selectors. For example, polysaccharide derivatives [6,7], cyclodextrins [8], macrocyclic antibiotics [9,10], cyclofructans [11,12], Π-acidic or Π-basic aromatic chiral compounds [13,14], cinchona alkaloids [15,16], chiral ligand exchange materials [17,18] and chiral crown ethers [19][20][21] have been widely used as chiral selectors for the development of CSPs. Those chiral selectors are based on an assemblage of repeating or non-repeating chiral subunits playing together for chiral recognition or based on a single chiral unit.…”

Section: Introductionmentioning

confidence: 99%

Preparation of Two New Diasteromeric Chiral Stationary Phases Based on (+)-(18-Crown-6)-2,3,11,12-tetracarboxylic Acid and (R)- or (S)-1-(1-Naphthyl)ethylamine and Chiral Tethering Group Effect on the Chiral Recognition

Agneeswari

Sung

et al. 2016

Molecules

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Abstract:Two new diastereomeric chiral stationary phases (CSPs) based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid as a chiral tethering group and a Π-basic chiral unit such as (R)-1-(1-naphthyl) ethylamine (CSP 1) or (S)-1-(1-naphthyl)ethylamine (CSP 2) were prepared. The two CSPs were applied to the enantiomeric separation of N-(3,5-dinitrobenzoyl)-1-phenylalkylamines and N-(3,5-dinitrobenzoyl)-α-amino acid derivatives using 20% isopropyl alcohol in hexane as a normal mobile phase. To elucidate the effect of the two chiral units on the chiral recognition, the chiral recognition abilities of the two CSPs were compared with each other and with that of a CSP (CSP 3) based on (R)-1-(1-naphthyl)ethylamine. From the chromatographic chiral recognition results, (R)-1-(1-naphthyl)ethylamine and (+)−(18-crown-6)-2,3,11,12-tetracarboxylic acid constituting CSP 1 were concluded to show a cooperative ("matched") effect on the chiral recognition while (S)-1-(1-naphthyl)ethylamine and (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid constituting CSP 2 were concluded to show an uncooperative ("mismatched") effect on the chiral recognition. From these results, it was concluded that (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid can be successfully used as a chiral tethering group for the preparation of new CSPs.

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“…That is why several governmental agencies such as the US Food and Drug Administration (FDA), concerning the enantiomeric purity of the optically active pharmaceutical ingredients (API). The majority of the pharmaceuticals are chiral in nature; however only few of them display the physiological activities, while the others could be inactive, responsible for some side effects or even toxic [2,3]. Chiral synthesis by using asymmetric reactants regarded as the most effective and economic procedure for manufacturing of enantiopure substances.…”

Section: Introductionmentioning

confidence: 99%

Preparation of l -tryptophan imprinted microspheres based on carboxylic acid functionalized polystyrene

Monier

Abdel-Latif

Nassef

2015

Journal of Colloid and Interface Science

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Development of an improved ligand exchange chiral stationary phase based on leucinol for the resolution of proton pump inhibitors

Cited by 14 publications

References 22 publications

Last ten years (2008–2018) of chiral ligand‐exchange chromatography in HPLC: An updated review

Last ten years (2008–2018) of chiral ligand‐exchange chromatography in HPLC: An updated review

Preparation of Two New Diasteromeric Chiral Stationary Phases Based on (+)-(18-Crown-6)-2,3,11,12-tetracarboxylic Acid and (R)- or (S)-1-(1-Naphthyl)ethylamine and Chiral Tethering Group Effect on the Chiral Recognition

Preparation of l -tryptophan imprinted microspheres based on carboxylic acid functionalized polystyrene

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