Macrocyclic Antibiotic Selectors in Direct HPLC Enantioseparations

Ilisz, István; Pataj, Zoltán; Aranyi, Anita; Péter, Antal

doi:10.1080/15422119.2011.596253

Cited by 58 publications

(47 citation statements)

References 154 publications

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“…Literature shows certain reviews [29,32] and monographs [33][34][35] on separation of AAs including enantioresolution. Several chromatographic [36][37][38] and electrophoretic methods [39,40] are based on using chiral stationary phases or chiral selectors as CMPA for separation of AA enantiomers.…”

Section: Methods For Direct Enantioseparationmentioning

confidence: 99%

Enantioresolution of Amino Acids: A Decade’s Perspective, Prospects and Challenges

Tanwar

Bhushan

2015

Chromatographia

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Section: Methods For Direct Enantioseparationmentioning

confidence: 99%

Enantioresolution of Amino Acids: A Decade’s Perspective, Prospects and Challenges

Tanwar

Bhushan

2015

Chromatographia

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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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“…The separation of enantiomers of unusual β-amino acids by high-performance liquid chromatography (HPLC) has been comprehensively investigated, and the results have been documented in several review papers (Ilisz et al, 2008(Ilisz et al, , 2010(Ilisz et al, , 2012a(Ilisz et al, , 2012b(Ilisz et al, , 2012c(Ilisz et al, , 2013. However, data relating to the HPLC analyses of fluorinated amino acids are very scarce, especially in the case of enantioseparation.…”

Section: Introductionmentioning

confidence: 99%

High‐performance liquid chromatographic enantioseparation of fluorinated cyclic β³‐amino acid derivatives on polysaccharide‐based chiral stationary phases. Comparison with nonfluorinated counterparts

Lajkó

Orosz

Kiss

et al. 2016

Biomedical Chromatography

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The stereoisomers of five fluorinated cyclic β(3) -amino acid derivatives and their nonfluorinated counterparts were separated on chiral stationary phases containing as chiral selectors cellulose tris-(3,5-dimethylphenyl carbamate), cellulose tris-(3-chloro-4-methylphenyl carbamate), cellulose tris-(4-methylbenzoate), cellulose tris-(4-chloro-3-methylphenyl carbamate), amylose tris-(3,5-dimethylphenyl carbamate) or amylose tris-(5-chloro-2-methylphenyl carbamate). The enantioseparations were carried out in normal-phase mode with n-hexane/alcohol/alkylamine mobile phases in the temperature range 5-40 °C. The effects of the mobile phase composition, the nature and concentration of the alcohol and alkylamine additives, the structures of the analytes and temperature on the separations were investigated. Thermodynamic parameters were calculated from plots of ln α vs. 1/T. The Δ(ΔH°) values ranged between -5.0 and +1.6 kJ/mol, while Δ(ΔS°) varied between -12.6 and +5.7 J/mol/K. The enantioseparation was enthalpically controlled, the retention factor and the separation factor decreasing with increasing temperature, but entropically controlled separation was also observed. The elution sequence was determined for all of the investigated analytes. Copyright © 2016 John Wiley & Sons, Ltd.

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Macrocyclic Antibiotic Selectors in Direct HPLC Enantioseparations

Cited by 58 publications

References 154 publications

Enantioresolution of Amino Acids: A Decade’s Perspective, Prospects and Challenges

Enantioresolution of Amino Acids: A Decade’s Perspective, Prospects and Challenges

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

High‐performance liquid chromatographic enantioseparation of fluorinated cyclic β³‐amino acid derivatives on polysaccharide‐based chiral stationary phases. Comparison with nonfluorinated counterparts

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Macrocyclic Antibiotic Selectors in Direct HPLC Enantioseparations

Cited by 58 publications

References 154 publications

Enantioresolution of Amino Acids: A Decade’s Perspective, Prospects and Challenges

Enantioresolution of Amino Acids: A Decade’s Perspective, Prospects and Challenges

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

High‐performance liquid chromatographic enantioseparation of fluorinated cyclic β3‐amino acid derivatives on polysaccharide‐based chiral stationary phases. Comparison with nonfluorinated counterparts

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High‐performance liquid chromatographic enantioseparation of fluorinated cyclic β³‐amino acid derivatives on polysaccharide‐based chiral stationary phases. Comparison with nonfluorinated counterparts