Liquid chromatographic resolution of racemic amino acids and their derivatives on a new chiral stationary phase based on crown ether

Hyun, Myung Ho; Jin, Jong Sung; Lee, Won–Jae

doi:10.1016/s0021-9673(98)00606-2

Cited by 171 publications

(106 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…One problem with this coated phase is stability. Recently, new crown ether phases using 18-crown-6-tetracarboxylic acid chemically bonded to aminopropylsilanized silica gel were prepared in different ways [152][153][154]. More recently, Hyun et al [155] prepared a crown ether phase derived from a (diphenyl-subsituted 1,1 0 -binaphthyl) crown ether.…”

Section: Synthetic Chiral Macrocyclesmentioning

confidence: 99%

Chiral separation by chromatographic and electromigration techniques. A Review

Gübitz

Schmid

2001

Biopharm & Drug Disp

225

135

View full text Add to dashboard Cite

This review gives a survey of different chiral separation principles and their use in high-performance liquid chromatography (HPLC), gas chromatography (GC), supercritical fluid chromatography (SFC), thin-layer chromatography (TLC), capillary electrophoresis (CE) and capillary electrochromatography (CEC) highlighting new developments and innovative techniques. The mechanisms of the different separation principles are briefly discussed and some selected applications are shown.

show abstract

Section: Synthetic Chiral Macrocyclesmentioning

confidence: 99%

Chiral separation by chromatographic and electromigration techniques. A Review

Gübitz

Schmid

2001

Biopharm & Drug Disp

225

135

View full text Add to dashboard Cite

show abstract

“…Chiral analysis has previously been achieved using various chiral selectors such as cyclodextrins (CDs) [6][7][8][9][10], antibiotics [11][12][13][14], and crown ethers [15][16][17][18]. However, despite good chiral recognition ability, these chiral selectors have several limitations resulting from low solubility, high cost, and difficult synthetic procedures.…”

Section: Introductionmentioning

confidence: 99%

Determination of Enantiomeric Compositions of Analytes Using Novel Fluorescent Chiral Molecular Micelles and Steady State Fluorescence Measurements

et al. 2007

View full text Add to dashboard Cite

Novel fluorescent chiral molecular micelles (FCMMs) were synthesized, characterized, and employed as chiral selectors for enantiomeric recognition of non-fluorescent chiral molecules using steady state fluorescence spectroscopy. The sensitivity of the fluorescence technique allowed for investigation of low concentrations of chiral selector (3.0×10 −5 M) and analyte (5.0×10 −6 M) to be used in these studies. The chiral interactions of glucose, tartaric acid, and serine in the presence of, and poly(sodium N-undecanoyl-L-phenylalininate) [poly-SUF] were based on diastereomeric complex formation. Poly-L-SUW had a significant fluorescence emission spectral difference as compared to poly-L-SUY and poly-L-SUF for the enantiomeric recognition of glucose, tartaric acid, and serine. Studies with the hydrophobic molecule α-pinene suggested that poly-L-SUY and poly-L-SUF had better chiral discrimination ability for hydrophobic analytes as compared to hydrophilic analytes. Partial-least-squares regression modeling (PLS-1) was used to correlate changes in the fluorescence emission spectra of poly-L-SUW due to varying enantiomeric compositions of glucose, tartaric acid, and serine for a set of calibration samples. Validation of the calibration regression models was determined by use of a set of independently prepared samples of the same concentration of chiral selector and analyte with varying enantiomeric composition. Prediction ability was evaluated by use of the root-mean-square percent relative error (RMS%RE) and was found to range from 2.04 to 4.06%.

show abstract

“…1) [1,2]. 이 키랄 고정상은 아미노산을 포함한 1차 아미노기를 가지는 라세미 화합물의 광학분리에 매우 효과적으로 이용되었다 [1][2][3][4][5][6][7][8][9][10].…”

Section: 서론unclassified

Comparative Enantiomer Separation on Chiral Stationary Phases Derived from Chiral Crown Ether by HPLC

황호¹,

전소희

김지연³

et al. 2012

KSBB Journal

View full text Add to dashboard Cite

1) Comparative liquid chromatographic enantiomer separation of α-amino acids, their esters and primary amino compounds was performed using two chiral stationary phases (CSPs) prepared by covalently bonding (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid (18-C-6-TA) of the same chiral selector. In general, the separation factors and resolution factors for these analytes on CSP 1 were greater than on CSP 2, while these capacity factors on CSP 2 were quite greater than on CSP 1. Except for leucine methyl ester and phenylalanine methyl ester, the elution orders of all analytes including α-amino α-alkyl acids and phenylglycine alkyl esters on CSP 1 are identical to those on CSP 2. This study showed that different connecting structures for these two CSPs might influence their ability to resolve the analytes depending on their structures related to the chiral recognition mechanism.

show abstract

Liquid chromatographic resolution of racemic amino acids and their derivatives on a new chiral stationary phase based on crown ether

Cited by 171 publications

References 20 publications

Chiral separation by chromatographic and electromigration techniques. A Review

Chiral separation by chromatographic and electromigration techniques. A Review

Determination of Enantiomeric Compositions of Analytes Using Novel Fluorescent Chiral Molecular Micelles and Steady State Fluorescence Measurements

Comparative Enantiomer Separation on Chiral Stationary Phases Derived from Chiral Crown Ether by HPLC

Contact Info

Product

Resources

About