Liquid chromatographic resolution of 2-hydroxycarboxylic acids on a new chiral stationary phase derived from (S)-leucine

Hyun, Myung Ho; Kang, Moon Hee; Han, Seung Chul

doi:10.1016/s0021-9673(99)01140-1

Cited by 26 publications

(5 citation statements)

References 18 publications

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“…The chiral recognition mechanism proposed in Figure 3a for the resolution of anilide derivatives 5 of N-acyl-aamino acids on CSP 1 is exactly identical with that proposed previously 13 for the resolution of anilide derivatives 4 of O-ethoxycarbonyl-2-hydroxycarboxylic acids on CSP 1. This is not surprising because the two types of analytes utilize identical interaction sites.…”

Section: Anilides Of N-acyl-a-amino Acidssupporting

confidence: 82%

“…13 The effectiveness of CSP 1 for the resolution of 2-hydroxycarboxylic acid derivatives 4 prompted us to investigate the resolution of anilide derivatives 5 of N-acyl-a-amino acids, which have structures similar to of 2-hydroxycarboxylic acid derivatives 4. p-Acidic or p-basic derivatives of a-amino acids resolvable on Pirkle-type CSPs have been generally prepared by the benzoylation of the amino group of a-amino acids. In contrast, anilide derivatives 5 are prepared through the carboxylic acid group of a-amino acids.…”

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confidence: 99%

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Liquid chromatographic resolution of N‐acyl‐α‐amino acids as their anilide derivatives on a chiral stationary phase based on (S)‐leucine

et al. 2002

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A chiral stationary phase (CSP 1) derived from N-(3,5-dinitrobenzoyl)leucine N-phenyl N-alkylamide was used for the liquid chromatographic resolution of anilide derivatives of N-acyl-alpha-amino acids and the chromatographic resolution results were compared with those from four other commercial CSPs. The chromatographic resolution results showed that CSP 1 was most effective among five CSPs used in this study. The chiral recognition mechanism exerted by CSP 1 for the resolution of anilide derivatives of N-acyl-alpha-amino acids is proposed to involve a face-to-face pi-pi interaction and two hydrogen bonding interactions between the CSP and the analytes from the chromatographic resolution behaviors of slightly modified anilide derivatives of N-acyl-alpha-amino acids. The chiral recognition mechanism proposed is quite similar to that advanced previously for the resolution of N-(3,5-methoxybenzoyl)-alpha-amino acids on CSP 1, even though the interaction sites of the two types of analytes were totally different from each other. The apparent similarity of the two chiral recognition mechanisms was assumed to stem from the identical interaction modes of the two types of analytes with the CSP. In addition, the dependence of the enantioselectivity of anilide derivatives of N-acyl-alpha-amino acids on the length of the alkyl tail of the N-acyl group of analytes was rationalized to stem from the intercalation of the N-acyl group of the (R)-enantiomer of analytes between the tethers of the CSP.

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Section: Anilides Of N-acyl-a-amino Acidssupporting

confidence: 82%

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confidence: 99%

Liquid chromatographic resolution of N‐acyl‐α‐amino acids as their anilide derivatives on a chiral stationary phase based on (S)‐leucine

et al. 2002

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“…The chiral recognition mechanism for the resolution of N ‐acyl derivatives ( 2 ) and N ‐ureide derivatives ( 3 ) of 3‐amino‐5‐phenyl‐1,4‐benzodiazepin‐2‐one on N ‐Phe‐ L ‐Leu, L ‐Leucine and D ‐Phenylglycine CSPs might be assumed to be identical to that for the resolution of N ‐benzyloxycarbonyl derivatives ( 1 ) because the three derivatives ( 1 , 2 , and 3 ) have identical structures except for the derivatizing group. The higher chiral recognition efficiency of N ‐Phe‐ L ‐Leu CSP compared to that of L ‐Leucine CSP for the resolution of N ‐acyl derivatives ( 2 ) and N ‐ureide derivatives ( 3 ) of 3‐amino‐5‐phenyl‐1,4‐benzodiazepin‐2‐one might be rationalized to be caused by the replacement of the NH hydrogen, a superfluous and non‐stereoselective retention site, of L ‐Leucine CSP with a phenyl group 9, 14…”

Section: Resultsmentioning

confidence: 99%

Liquid chromatographic resolution of 3‐amino‐1,4‐benzodiazepin‐2‐one derivatives on various Pirkle‐type chiral stationary phases

2011

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The two enantiomers of N-acyl amide and N-ureide derivatives of 3-amino-5-phenyl-1,4-benzodiazepin-2-ones, which have been known to show anti-respiratory syncytial virus (RSV) activity, were resolved on seven different Pirkle-type chiral stationary phases (CSPs) with the use of 10% isopropyl alcohol in hexane as a mobile phase. Among the seven Pirkle-type CSPs, the one based on (S)-leucine derivative named as N-Phe-L-Leu was found to be most successful, the separation factors (α) and the resolutions (R(S) ) for seven analytes being in the range of 1.78-4.21 and 5.94-15.08, respectively. By resolving N-benzyloxycarbonyl derivatives of 3-amino-5-phenyl(or 5-methyl)-1,4-benzodiazepin-2-ones on Pirkle-type CSPs, the phenyl ring at the 5-position and the NH hydrogen at the 1-position of analytes were found to play an important role in the chiral recognition.

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“…Different studies have approached the enantioseparation of 2-hydroxycarboxylic acids. Some of them are ligand exchange CE [19][20][21], ligand exchange LC [22], GC analysis after derivatization [23], LC after derivatization [24], direct LC by using macrocyclic antibiotic chiral stationary phases (CSPs) [25][26][27], and quinine-or quinidine-derived CSPs [28][29][30][31][32][33], amongst others.…”

Section: F I G U R E 1 Structures Of the Studied 2-hydroxycarboxylic mentioning

confidence: 99%

Chiral separation of disease biomarkers with 2‐hydroxycarboxylic acid structure

Calderón

SANTI

Lämmerhofer

2017

J of Separation Science

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Chiral 2-hydroxycarboxylic acids are compounds that have been linked to particular diseases and are putative biomarkers with some diagnostic potential. The importance of identifying whether a particular enantiomer is related to certain diseases has been encouraged recently. However, in many cases it has not yet been elucidated whether there are stereochemical implications with respect to these biomarkers and whether their enantioselective analysis provides new insights and diagnostic potential. In this study 13 disease-related chiral 2-hydrocarboxylic acids were studied for their chiral separation by high-performance liquid chromatography on three cinchona alkaloid-derived chiral stationary phases. From a subgroup of eight 2-hydroxymonocarboxylic acids, baseline resolution could be achieved and inversion of elution order by exchanging tert-butylcarbamoyl quinidine chiral stationary phase (Chiralpak QD-AX) for the corresponding quinine analogue (Chiralpak QN-AX) is shown for seven of them. Furthermore, conditions for chiral separation of the 2-hydroxydicarboxylic acids, citramalic acid, 2-isopropylmalic acid, and 2-hydroxyadipic acid are reported and compared to the previous reported conditions for 2-hydroxyglutaric acid and malic acid.

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Liquid chromatographic resolution of 2-hydroxycarboxylic acids on a new chiral stationary phase derived from (S)-leucine

Cited by 26 publications

References 18 publications

Liquid chromatographic resolution of N‐acyl‐α‐amino acids as their anilide derivatives on a chiral stationary phase based on (S)‐leucine

Liquid chromatographic resolution of N‐acyl‐α‐amino acids as their anilide derivatives on a chiral stationary phase based on (S)‐leucine

Liquid chromatographic resolution of 3‐amino‐1,4‐benzodiazepin‐2‐one derivatives on various Pirkle‐type chiral stationary phases

Chiral separation of disease biomarkers with 2‐hydroxycarboxylic acid structure

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