Enantiomeric separation of nonproteinogenic amino acids by high-performance liquid chromatography

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

doi:10.1016/j.chroma.2012.07.011

Cited by 47 publications

(25 citation statements)

References 291 publications

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“…Various methods have been reported to distinguish the chirality of amino acids, including high performance liquid chromatography 8–10 , gas chromatography 11 , mass spectrometry 12 , electrochemistry 13–15 , and capillary electrophoresis 16, 17 . However, most of these techniques require complicated sample pretreatment and sophisticated instrumentation which makes them impractical for real-time analysis.…”

Section: Introductionmentioning

confidence: 99%

Time-Resolved Visual Chiral Discrimination of Cysteine Using Unmodified CdTe Quantum Dots

Ghasemi

Hormozi-Nezhad

2017

Sci Rep

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Herein, we demonstrate a simple yet novel luminescence assay for visual chiral discrimination of cysteine. Thioglycolic acid (TGA)-capped cadmium-telluride (CdTe) quantum dots (QDs) exposing green emission were directly synthesized in aqueous solution. The interaction between cysteine molecules and CdTe QDs induced the aggregation of QDs via hydrogen bonding. As a result of electronic coupling within these aggregates, a redshift both in the absorption and emission spectra of QDs occured. The difference in the kinetics of the interactions between L- and D-cysteine with CdTe QDs led to chiral recognition of these enantiomers. Addition of D-cysteine to CdTe QDs in a basic media caused a green-to-yellow color change, while no color alteration in QDs emission was observed in the presence of L-cysteine after 2 hours. Notably, the QDs used in the proposed assay are free from any labling/modification, which makes the present strategy highly attractive for sensing applications. Furthermore, the presented chiral assay is able to determine the enantiomeric excess (ee) of D-cysteine in the whole range of ee values (from −100% to 100%).

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Section: Introductionmentioning

confidence: 99%

Time-Resolved Visual Chiral Discrimination of Cysteine Using Unmodified CdTe Quantum Dots

Ghasemi

Hormozi-Nezhad

2017

Sci Rep

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“…In addition to the experimental works for chiral separation of amino acids and other chiral compounds, in recent years, with the development of computational chemistry, theoretical studies have been performed to predict potential ability of chiral separating agents to resolution of enantiomers [33][34][35][36][37][38][39][40][41]. For example, Lipkowitz in his review pointed to theoretical papers that used cyclodextrin for separation of chiral compounds [37].…”

Section: Introductionmentioning

confidence: 99%

Enantiomeric discrimination of leucine enantiomers by nanotubular cyclic peptides: DFT and ONIOM calculation of the absorption spectra of guested enantiomers

Shahangi

Chermahini

Farrokhpour

et al. 2016

J Incl Phenom Macrocycl Chem

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In this work, the inclusion complexes of leucine as the guest and a series of cyclic peptides with four to nine alanine as building block (host molecules) were investigated by M062X/6-31 ? G (d) level of theory. The calculations predicted the stability of the enantiomers in the cavity of cyclic peptides and the possibility of distinction between the enantiomers for the used level of theory. The results indicated that the most stable aggregate is formed between CyclAla9 and R and S-leucine enantiomers and CyclALA4 have the least interaction with R and S-leucine enantiomers. Geometrical changes of leucine due to complexation and hydrogen bonding were considered. The NBO calculations for analyzing the nature of the intermolecular hydrogen bonds were performed. In another part of this work, the UV absorption spectra of complexes of R, and S-leucine with CyclAla9 calculated using ONIOM method in the gas phase and it was showed that the UV absorption spectroscopy could be used as a chirality discriminator tool in recognition of enantiomers in the gas phase.

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“…The demand for single enantiomers in developing chiral drugs is met by the development of new strategies toward asymmetric synthesis and new methods of chiral separation. To date, chiral separation on analytical or semipreparative scales has been achieved using gas chromatography (GC) [4], highperformance liquid chromatography (HPLC) [5], supercritical-fluid chromatography (SFC) [6] and capillary electrophoresis (CE) [7] to meet the need to characterize chiral compounds to a greater extent and with greater accuracy and precision. Among these techniques, CE stands out due to its advantages in affording rapid separations with high resolution and efficiency at elevated electric fields and selective separation modes.…”

Section: Introductionmentioning

confidence: 99%

Recent development of cationic cyclodextrins for chiral separation

Zhou

Tang

2015

TrAC Trends in Analytical Chemistry

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Enantiomeric separation of nonproteinogenic amino acids by high-performance liquid chromatography

Cited by 47 publications

References 291 publications

Time-Resolved Visual Chiral Discrimination of Cysteine Using Unmodified CdTe Quantum Dots

Time-Resolved Visual Chiral Discrimination of Cysteine Using Unmodified CdTe Quantum Dots

Enantiomeric discrimination of leucine enantiomers by nanotubular cyclic peptides: DFT and ONIOM calculation of the absorption spectra of guested enantiomers

Recent development of cationic cyclodextrins for chiral separation

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