Liquid chromatographic enantiomer resolution of <i>N</i>‐fluorenylmethoxycarbonyl α‐amino acids and their ester derivatives on polysaccharide‐derived chiral stationary phases

Li, Yin Hua; Lee, Won–Jae

doi:10.1002/jssc.200500183

Cited by 8 publications

(5 citation statements)

References 21 publications

(20 reference statements)

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“…Particularly, polysaccharide-derived CSPs have been widely and successfully used for separating a variety of enantiomer compounds [2][3][4] . Related to this study, we have been reported enantiomer separation of α-amino acids and/or esters as several aromatic moiety derivatives using these polysaccharide-derived CSPs [5][6][7][8] . In this study, we focused on nitrobenzoxadiazole (NBD) group which is a fluorescence active derivatizing group of α-amino acids esters, because NBD fluorescence detection may provide strong advantages of selectivity and sensitivity in enantiomer separation.…”

Section: Introductionmentioning

confidence: 89%

Liquid Chromatographic Enantiomer Separation of α-Amino Acid Esters as Nitrobenzoxadiazole Derivatives Using Polysaccharide-Derived Chiral Stationary Phases

Islam¹,

Lee²

2015

Journal of the Chosun Natural Science

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Liquid chromatographic enantiomer separation of α-amino acid esters as nitrobenzoxadiazole (NBD) derivatives was performed using several chiral stationary phases (CSPs) based on polysaccharide derivatives under fluorescence detection. For enantiomer separation by normal HPLC, the non-aqueous derivatization method of α-amino acid esters for NBD analytes was introduced. Among the six CSPs used in this study, the performance of Chiralpak IA was superior for enantiomer resolution of NBD derivatives of several α-amino acid methyl esters. Also the convenient analytical method using polysaccharide-derived CSPs developed in this study was applied to determine the optical purity of α-amino acids esters. It was investigated that the enantiomeric impurity levels of 0.02-1.73% were found after determination of enantiomeric purities of several commercially available L-amino acid methyl esters. It is expected to be quite useful for enantiomer separation of other α-amino acid esters as NBD derivatives by normal HPLC.

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Section: Introductionmentioning

confidence: 89%

Liquid Chromatographic Enantiomer Separation of α-Amino Acid Esters as Nitrobenzoxadiazole Derivatives Using Polysaccharide-Derived Chiral Stationary Phases

Islam¹,

Lee²

2015

Journal of the Chosun Natural Science

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“…효율적인 광학분리를 위해 의약품개발 에서 흔히 사용되는 amino group이 보호된 α-amino acid 나 이들 유도체들의 광학분리를 수행하였다 [1][2][3]. 특히 α-amino acid ester의 경우에는 benzophenone imine Schiff base나 9-anthraldimine으로 이들을 유도체화 한 후에, 여러 키랄 고정 상에서 광학분리하는 새로운 분석법도 발표하였다 [4][5][6].…”

Section: 서론unclassified

Enantiomer Separation of α-Amino Acid Esters as Nitrobenzoxadiazole Derivatives Using Chiral Columns

윤원남¹,

김지연²,

이원재³

2013

KSBB Journal

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A new convenient derivatization method of α-amino acid esters as nitrobenzoxadiazole (NBD) derivatives for chiral resolution was introduced and the enantiomer separation of α-amino acid esters as NBD derivatives was performed by normal HPLC using chiral columns based on polysaccharide derivatives. The NBD derivatives were readily prepared by stirring NBD-Cl and α-amino acid methyl ester HCl with NaHCO 3 in ethanol. The performance of Chiralpak IA was superior to the other chiral stationary phases for enantiomer resolution of NBD derivatives of several α-amino acid methyl esters. Owing to fluorescence detection as well as strong UV absorption, it is expected that the convenient analytical method developed in this study will be very useful for enantiomer separation of α-amino acid esters as NBD derivatives on polysaccharide-derived chiral columns.

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“…Similarly, the introduction of the fluorenylmethyloxycarbonyl group (Fmoc) might require additional protection of the serine hydroxyl group [13,14] which makes the preparation of serine analytes more complicated (Figure 1C). To our best knowledge, only a few studies dealing with enantiosepa-ration of serine esters were published [25][26][27][28][29], all focusing only on short alkyl (methyl or ethyl) esters. Moreover, chromatographic enantioseparations of serine esters were conducted under normal phase conditions requiring toxic non-polar solvents and often toxic trifluoroacetic acid as an additive, too.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective high‐performance liquid chromatography of aryl‐substituted oxazolines as an efficient tool for determination of chiral purity of serine medicinal components

Pomeisl

Vaňkátová

Hamplová

2022

J of Separation Science

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A new approach for the evaluation of chiral purity of serine esterification products bearing long-chain alkyl substituents was developed. The compounds were simply converted to aryl-substituted oxazolines which: (i) facilitates effective chromatographic enantioseparation and (ii) enables direct detection using ultraviolet absorption. The method employs a polysaccharide-based chiral stationary phase and allows enantioseparation of highly stable oxazoline products in less than 6 min using a simple binary mobile phase. As opposed to the previously used normal phase method the developed method was performed in the reversed-phase mode. Aside from the benefits of switching to less hazardous solvents with regard to the principles of Green Chemistry, this has also led to a reduction in the analysis time. In comparison with known serine chromophores, the best enantioseparation of aryloxazoline rigid structure may be achieved only based on non-polar interactions with the chiral stationary phase.In contrast, the substitution of the chromophore moiety with hydroxyl substituent affected intra and intermolecular interactions that caused enantioseparation differences. Concurrently, we found high chirality retention of (R)-and (S)-configuration oxazoline standards (≥99% enantiomeric excess) during the introduction of the ultraviolet label. The method is suitable for rapid injection of the mixture containing the ultraviolet absorption marker without prior purification.

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Liquid chromatographic enantiomer resolution of N‐fluorenylmethoxycarbonyl α‐amino acids and their ester derivatives on polysaccharide‐derived chiral stationary phases

Cited by 8 publications

References 21 publications

Liquid Chromatographic Enantiomer Separation of α-Amino Acid Esters as Nitrobenzoxadiazole Derivatives Using Polysaccharide-Derived Chiral Stationary Phases

Liquid Chromatographic Enantiomer Separation of α-Amino Acid Esters as Nitrobenzoxadiazole Derivatives Using Polysaccharide-Derived Chiral Stationary Phases

Enantiomer Separation of α-Amino Acid Esters as Nitrobenzoxadiazole Derivatives Using Chiral Columns

Enantioselective high‐performance liquid chromatography of aryl‐substituted oxazolines as an efficient tool for determination of chiral purity of serine medicinal components

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