Enantiomeric Separation of Underivatized Amino Acids: Predictability of Chiral Recognition on Ristocetin A Chiral Stationary Phase

Wagdy, Hebatallah A.; Hanafi, Rasha S.; El‐Nashar, Rasha M.; Aboul‐Enein, Hassan Y.

doi:10.1002/chir.22291

Cited by 11 publications

(7 citation statements)

References 19 publications

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“…Using newer CSPs, the enantioseparation of structurally similar analytes, enantiomers of related amino acids, for example, phenylalanine and tryptophan, cannot be performed, because co‐elution was observed (similar values of elution times). This trend was also described in works dedicated to enantioseparation on cyclofructan CSP in polar organic separation mode (Moravčík & Hroboňová, 2013), ristocetin CSP in RP mode (Wagdy, Hanafi, El‐Nashar, & Aboul‐Enein, 2014), or ion‐exchange type CSP in RP mode (Zhang, Holder, Franco, & Lindner, 2014). For this reason and also due to the correlation of other substances and the separation and determination of structurally similar amino acids in real samples, the proposed 2D‐LC method has great importance.…”

Section: Resultsmentioning

confidence: 55%

Application of achiral–chiral two‐dimensional HPLC for separation of phenylalanine and tryptophan enantiomers in dietary supplement

Lomenová

Hroboňová

2020

Biomedical Chromatography

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This study developed a two‐dimensional heart‐cutting LC method for the separation of amino acid enantiomers. Two approaches for achiral separation of amino acids, phenylalanine and tryptophan, were selected. Amino acids were separated on C18 or hydrophilic interaction liquid chromatography (HILIC) columns in first dimension after their enantiomer separation on a teicoplanin chiral column in second dimension. Mobile phases for both separation systems were optimized by testing different types of organic modifiers, concentrations of ion‐pair agent (sodium 1‐octanesulfonate), and ionic modifier (ammonium acetate). The resolution of enantiomers higher than 1.5 for both amino acids was achieved using a C18–teicoplanin coupled column separation system with mobile phases methanol/2 mM sodium 1‐octanesulfonate (10:90 and 75:25, step gradient between achiral and chiral columns, respectively). The lower resolution of amino acid enantiomers (RS ˃ 0.9), but higher column efficiency, was achieved on a HILIC–teicoplanin separation system with mobile phases acetonitrile/50 mM ammonium acetate (90:10 and 80:20, step gradient between achiral and chiral columns, respectively). The developed heart‐cutting 2D‐LC methods were validated in terms of linearity, limit of detection, limit of quantification, precision, and accuracy. The results suggested that the developed methods were applicable for the simultaneous determination of amino acid enantiomers in the dietary supplement. The sample contained l‐phenylalanine and l‐tryptophan.

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Section: Resultsmentioning

confidence: 55%

Application of achiral–chiral two‐dimensional HPLC for separation of phenylalanine and tryptophan enantiomers in dietary supplement

Lomenová

Hroboňová

2020

Biomedical Chromatography

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“…One of the possibilities for separation and determination of amino acid enantiomers is direct HPLC separation by using stationary phases consist of chiral selectors with different functionalities. Indicated by number of published papers, this type of chiral separations are well researched and according to literature, the most popular chiral stationary phase (CSP) for enantioseparations of amino acids are based on macrocyclic antibioticsteicoplanin (Kučerová et al 2013;Taujenis et al 2014;Min et al 2015;Riesová et al 2016;Hroboňová et al 2017), teicoplanin aglycone (Bystrická et al 2016;Hroboňová et al 2015), ristocetin (Wagdy et al 2014;Lomenova and Hroboňová 2018), vancomycin (Deáková et al 2015); polysacharide based chiral stationary phasescyclodextrins (Kučerová et al 2016;Hroboňová et al 2017), cyclofructans (Hroboňová et al 2017), amylose (Kučerová et al 2013;Riesová et al 2016) and chiral ion exchangers (Reischl et al 2011;Woiwode et al 2018;Geibel et al 2019. Beside of commercially available CSPs, the innovative stationary phases to reach chiral separations are based on molecularly imprinted polymers. These sorbents are the most applied in field of affinity chromatography.…”

Section: Efficiency Of Separation Using Mip Chiral Stationary Phasesmentioning

confidence: 99%

Preparation and application of molecularly imprinted polymers for chiral HPLC separation of biologically active substances

Lomenová¹,

Hroboňová²

2020

NBC

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Chiral separations are one of the important analytical tasks, since there are increasing demands for production of enantiomerically pure compounds. The separation and determination of enantiomers find applications in pharmaceutical and food analysis, and it is necessary to pay attention to the development and improvement of chiral analytical methods. High performance liquid chromatography (HPLC) with chiral stationary phase (CSP) based on molecularly imprinted polymers (MIPs) is perspective way. One of the main advantage of these stationary phases is the possibility of predetermining the elution order of enantiomers. The presented work is focused on the methods of preparation and the applications of selective sorption materials (MIPs) in the field of HPLC separation of biologically active substances, amino acids. This review contains comprehensive informations about MIP-amino acid synthesis: compositions of polymerization mixture (monomer, template, cross-linker, porogen), type of polymerization and polymerization conditions, what can affect final efficiency of enantioseparation. The most used porogen was toluene, crosslinker ethylene glycol dimethacrylate (EDMA) and initiator azoisobutyronitrile (AIBN). MIP CSP prepared for derivatized amino acids show better results (higher resolution) than MIP prepared for underivatized amino acids. MIP are very promising material to be used as stationary phase in HPLC, although further developments and new approaches are necessary to fully exploit their potential.

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“…Amino acids or their derivatives have been enantioseparated on ligand-exchange chiral stationary phases (CSPs), 2 cyclodextrin CSPs, [3][4][5] crown-ether CSPs, 6,7 macrocyclic glycopeptide-based CSPs, [8][9][10] polysaccharide-based CSPs 11 and protein-based CSPs 12 in the past twenty years. Amino acids or their derivatives have been enantioseparated on ligand-exchange chiral stationary phases (CSPs), 2 cyclodextrin CSPs, [3][4][5] crown-ether CSPs, 6,7 macrocyclic glycopeptide-based CSPs, [8][9][10] polysaccharide-based CSPs 11 and protein-based CSPs 12 in the past twenty years.…”

Section: Introductionmentioning

confidence: 99%

“…HPLC offers several ways to the enantiomeric separation of amino acids. Amino acids or their derivatives have been enantioseparated on ligand-exchange chiral stationary phases (CSPs), 2 cyclodextrin CSPs, [3][4][5] crown-ether CSPs, 6,7 macrocyclic glycopeptide-based CSPs, [8][9][10] polysaccharide-based CSPs 11 and protein-based CSPs 12 in the past twenty years. Cyclofructans (CFs) are a novel type of chiral selectors that were introduced in 2009.…”

Section: Introductionmentioning

confidence: 99%

Determination of methionine enantiomers by HPLC on the cyclofructan chiral stationary phase

et al. 2015

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The enantiomeric separation of methionine by high performance liquid chromatography on various cyclofructan type chiral stationary phases in the polar-organic separation mode was studied. The effects of the mobile phase composition and temperature on the enantioselectivity of the enantiomers were investigated. The enantioselective separation was attained on the isopropylcarbamate cyclofructan 6 chiral stationary phase with methanol/acetonitrile/acetic acid/triethylamine (75/25/0.3/ 0.2 v/v/v/v) as a mobile phase. The low retention and no separation were observed on the dimethylphenyl carbamate cyclofructan 7 and naphthylethyl carbamate cyclofructan 6 chiral stationary phases. Three types of detection, low-wavelength UV, polarimetric, and circular dichroism, were used.The UV detection limit for enantiomers was 11 mg mL À1 (S/N ¼ 3) and the polarimetric and circular dichroism detection limits were 10 and 8 times lower. Good linearity was observed from 50 to 500 mg mL À1 . The proposed method was applied to determine D-and L-methionine in a dietary supplement sample.

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Enantiomeric Separation of Underivatized Amino Acids: Predictability of Chiral Recognition on Ristocetin A Chiral Stationary Phase

Cited by 11 publications

References 19 publications

Application of achiral–chiral two‐dimensional HPLC for separation of phenylalanine and tryptophan enantiomers in dietary supplement

Application of achiral–chiral two‐dimensional HPLC for separation of phenylalanine and tryptophan enantiomers in dietary supplement

Preparation and application of molecularly imprinted polymers for chiral HPLC separation of biologically active substances

Determination of methionine enantiomers by HPLC on the cyclofructan chiral stationary phase

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