Direct chromatographic enantioresolution of fully constrained β-amino acids: exploring the use of high-molecular weight chiral selectors

Sardella, Roccaldo; Ianni, Federica; Lisanti, Antonella; Scorzoni, Stefania; Marini, Francesca; Sternativo, Silvia; Natalini, Benedetto

doi:10.1007/s00726-014-1683-5

Cited by 21 publications

(6 citation statements)

References 38 publications

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“…[25][26][27] Thereby, additives regulate the strength of the ionic interactions between selector and analyte molecules. They influence the solvation extent of both interaction partners (i.e., the formation of an ion-cloud around the charged sites and of a double layer of a particular thickness in dependence on the ionic strength on the charged surface, respectively) and act as displacers, which may result in a profound impact on the retention and the quality of the enantioseparation process 25,[28][29][30][31] .…”

Section: Effect Of Basic and Acidic Additivesmentioning

confidence: 99%

Quinine‐Based Zwitterionic Chiral Stationary Phase as a Complementary Tool for Peptide Analysis: Mobile Phase Effects on Enantio‐ and Stereoselectivity of Underivatized Oligopeptides

et al. 2015

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Peptide stereoisomer analysis is of importance for quality control of therapeutic peptides, the analysis of stereochemical integrity of bioactive peptides in food, and the elucidation of the stereochemistry of peptides from a natural chiral pool which often contains one or more D-amino acid residues. In this work, a series of model peptide stereoisomers (enantiomers and diastereomers) were analyzed on a zwitterionic ion-exchanger chiral stationary phase (Chiralpak ZWIX(+) 5 µm), in order to investigate the retention and separation performance for such compounds on this chiral stationary phase and elucidate its utility for this purpose. The goal of the study focused on 1) investigations of the effects of the sample matrix used to dissolve the peptide samples; 2) optimization of the mobile phase (enabling deriving information on factors of relevance for retention and separation); and 3) derivation of structure-selectivity relationships. It turned out that small di- and tripeptides can be well resolved under optimized conditions, typically with resolutions larger than 1.5. The optimized mobile phase often consisted of methanol-tetrahydrofuran-water (49:49:2; v/v/v) with 25 mM formic acid and 12.5 mM diethylamine. This work proposes some guidance on which mobile phases can be most efficiently used for peptide stereoisomer separations on Chiralpak ZWIX. Chirality 28:5-16, 2016. © 2015 Wiley Periodicals, Inc.

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Section: Effect Of Basic and Acidic Additivesmentioning

confidence: 99%

Quinine‐Based Zwitterionic Chiral Stationary Phase as a Complementary Tool for Peptide Analysis: Mobile Phase Effects on Enantio‐ and Stereoselectivity of Underivatized Oligopeptides

et al. 2015

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“…Apparent thermodynamic parameters have been calculated, and entropically-and enthalpically-driven separations discussed as part of the molecular recognition process. The enantioresolutions of free unusual AAs and constraint -AAs on teicoplanin-and polysaccharide-based columns have been compared[26,27]. The optimized methods proved applicable for enantiomeric purity (enantiomeric excess, ee) control.[27].…”

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confidence: 99%

State-of-the-art enantioseparations of natural and unnatural amino acids by high-performance liquid chromatography

Ilisz

Péter

Lindner

2016

TrAC Trends in Analytical Chemistry

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This review discusses recent publications on the separation and analysis of natural and unnatural amino acid enantiomers by liquid chromatography. Focus is placed on methodological aspects relating chiral stationary phases and chiral columns which can cope with the challenge. Conceptually, amino acids can be enantioseparated in free form, which refers to the resolution of polar ampholytes, or as N-protected amino acids, which can be regarded as acidic commodities. Such synthons are used, for instance, in peptide synthesis protocols. Amino groups are frequently tagged with highly fluorescent or MS/MS active labels in order to generate sensitive and simultaneously stereoselective assays of diverse amino acids in complex matrices. It is our intention to present the state of the art of enantioselective amino acid analysis by HPLC concepts and to pinpoint practical aspects.

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“…If chiral cavities are opened, the inclusion interactions of the analyte are reduced and the retention time of the analyte is reduced [ 24 , 28 , 29 , 30 ]. Pirkle and Welch studied the effect of an alcohol modifier on enantioselectivity and found that the effect of a modifier depends on the structure of the analyte [ 31 , 32 , 33 ]. Based on VCD measurements Grinberg et al observed conformational changes of the chiral stationary phase in the presence of polar solvents.…”

Section: Resultsmentioning

confidence: 99%

Application of Green Chiral Chromatography in Enantioseparation of Newly Synthesized Racemic Marinoepoxides

Buljan

Roje

2022

Marine Drugs

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Enantioseparation of the newly synthesized series of novel quinoline-2(1H)-one epoxide structures rac-6a–c and rac-8a–c, named marinoepoxides, is described. Marinoepoxide rac-6a, the key intermediate in the total synthesis of natural products marinoaziridines A and B, as well as their structural analogues, was synthesized by addition of the achiral ylide generated in situ from the sulfonium salt 5 or 7, to the carbon-oxygen double bond of the corresponding quinoline-2(1H)-one-4-carbaldehyde 4a–c in good yield. Separation of enantiomers of (±)-2,3,3-trisubstituted marinoepoxides rac-6a–c and (±)-trans-2,3-disubstituted marinoepoxides rac-8a–c was studied using two immobilized polysaccharide type chiral stationary phases (CSPs); tris-(3,5-dichlorophenylcarbamoyl)cellulose stationary phase (CHIRAL ART Cellulose-SC) and tris-(3,5-dimethylphenylcarbamoyl)amylose stationary phase (CHIRAL ART Amylose-SA). Enantioseparation conditions were explored by high-performance liquid chromatography (HPLC) using dimethyl carbonate/alcohol mixtures and n-hexane/ethanol (80/20, v/v) as mobile phase, and by supercritical fluid chromatography (SFC) using CO2/alcohol mixtures as mobile phase. In all examined racemates, enantioseparation was successfully achieved, but its efficiency largely depended on the structure of chiral selector and type/composition of the mobile phase.

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Direct chromatographic enantioresolution of fully constrained β-amino acids: exploring the use of high-molecular weight chiral selectors

Cited by 21 publications

References 38 publications

Quinine‐Based Zwitterionic Chiral Stationary Phase as a Complementary Tool for Peptide Analysis: Mobile Phase Effects on Enantio‐ and Stereoselectivity of Underivatized Oligopeptides

Quinine‐Based Zwitterionic Chiral Stationary Phase as a Complementary Tool for Peptide Analysis: Mobile Phase Effects on Enantio‐ and Stereoselectivity of Underivatized Oligopeptides

State-of-the-art enantioseparations of natural and unnatural amino acids by high-performance liquid chromatography

Application of Green Chiral Chromatography in Enantioseparation of Newly Synthesized Racemic Marinoepoxides

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