Enantioseparation of dansyl amino acids by HPLC on a monolithic column dynamically coated with a vancomycin derivative

Pittler, Elfriede; Schmid, Martin G.

doi:10.1002/bmc.1430

Cited by 24 publications

(27 citation statements)

References 62 publications

(63 reference statements)

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“…In recent years, a new type of HPLC column (coated dynamically by the use of monolithic RP 18 and vancomycin‐derivatives as chiral selector) has been widely applied in enantioseparation of dansyl amino acids by HPLC (Pittler and Schmid, ). HPLC analysis was performed on the commercially available monolithic column Chromolith (RP 18 , 100 × 4.6 mm).…”

Section: Enantiomeric Separation Of Amino Acids By Hplc Methodsmentioning

confidence: 99%

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Application of TLC, HPLC and GC methods to the study of amino acid and peptide enantiomers: a review

Dołowy

Pyka

2013

Biomedical Chromatography

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Amino acids are very important organic compounds in nature. The biological activity of amino acids depends mainly on their stereoisomeric configuration (d- or l-). Thus, the stereochemical analysis of amino acids and peptides is an important aspect of their characterization. Owing to the increasing role of amino acid configuration in biomedical and pharmaceutical studies, numerous analytical methods have been described in the literature. Among a wide range of analytical techniques available for the steroselective separation of different amino acids, which were obtained from plants or biological samples, chromatographic methods such as thin-layer chromatography, high-performance chromatography and also gas chromatography are very useful. This review presents such systems developed for direct stereoisomeric separation and quantitative determination of amino acid and peptide enantiomers with emphasis on selected literature published during two last decades. Almost all aspects, including sample preparation prior chromatographic analysis, stationary phase, solvent system and detection system, are discussed. New possibilities in chiral amino acid analysis have been opened up by the application of mass spectrometry and infrared detection in thin-layer chromatography and mass spectrometry-selected ion monitoring detection system in gas chromatography. A modern trend in high-performance chromatography is two-dimensional chromatography. These innovations have led to decreased development time and increased amino acid resolution and detectability.

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Section: Enantiomeric Separation Of Amino Acids By Hplc Methodsmentioning

confidence: 99%

“…50:50 (v/v), was used. Detection was made under UV (Pittler and Schmid, ). Another approach is the use of d ‐penicillamine‐Cu (II) complex as a chiral selector to chromatographic separation of cyclic β ‐substituted α ‐amino acids (Schlauch et al ., ).…”

Section: Enantiomeric Separation Of Amino Acids By Hplc Methodsmentioning

confidence: 99%

Application of TLC, HPLC and GC methods to the study of amino acid and peptide enantiomers: a review

Dołowy

Pyka

2013

Biomedical Chromatography

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“…Pittler et al. coated a vancomycin derivative on an RP HPLC column. The authors attached a hydrophobic alkyl chain to vancomycin for immobilization of the chiral selector on the RP material.…”

Section: Comparison Of Chiral Separations In Different Modalities Of Lcmentioning

confidence: 99%

Advances in enantiomeric resolution on monolithic chiral stationary phases in liquid chromatography and electrochromatography

2014

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During the last decade, chiral monolithic stationary phases have been prepared and used for rapid enantioseparations in CEC and HPLC. Various chiral selectors are used to prepare these CSPs. The preparation, properties, and applications of these CSPs are discussed in this paper. Attempts have been made to describe optimization strategies and the chiral recognition mechanisms. A comparison of chiral separations in CEC and HPLC is described. Efforts have also been made to predict the future perspectives and challenges of chiral monolithic stationary phases. The most effective chiral selectors include polysaccharides, cyclodextrins, and macrocyclic glycopeptide antibiotics. These chiral phases produced acceptable analytical enantiomeric separation of a variety of racemates. However, the development of these CSPs for preparative-scale separations is needed.

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“…For example, click chemistry can be used to prepare cyclodextrin‐based CSPs , in addition to the chemical incorporation of a chiral selector into the monolithic stationary phase (SP) . Dynamic coating is an alternative approach for SP preparation, which is characterized by efficiency, simplicity, and speed of preparation . Pittler et al.…”

Section: Introductionmentioning

confidence: 99%

The degree of substitution affects the enantioselectivity of sulfobutylether‐β‐cyclodextrin chiral stationary phases

et al. 2019

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Three chiral stationary phases were prepared by dynamic coating of sulfobutylether‐β‐cyclodextrin (SBE‐β‐CD) with different degrees of substitution, onto strong anion‐exchange stationary phases. The enantioselective potential and stability of newly prepared chiral stationary phases were examined using a set of structurally different chiral analytes. Measurements were performed in RP‐HPLC. Mobile phases consisted of methanol/formic acid, pH 2.10, and methanol/10 mM ammonium acetate buffer, pH 4.00, in various volume ratios. SBE‐β‐CDs with degrees of substitution (DS) 4, 6.3, and 10 proved suitable for the enantioseparation of 14, 11, and 8 analytes, respectively. The SBE‐β‐CD DS 4 based chiral stationary phase enabled the enantioseparation of the nearly all basic and neutral compounds. Chiral stationary phases with higher sulfobutylether‐β‐cyclodextrin substitution (especially DS 10) yielded higher enantioresolution values for acidic compounds.

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Enantioseparation of dansyl amino acids by HPLC on a monolithic column dynamically coated with a vancomycin derivative

Cited by 24 publications

References 62 publications

Application of TLC, HPLC and GC methods to the study of amino acid and peptide enantiomers: a review

Application of TLC, HPLC and GC methods to the study of amino acid and peptide enantiomers: a review

Advances in enantiomeric resolution on monolithic chiral stationary phases in liquid chromatography and electrochromatography

The degree of substitution affects the enantioselectivity of sulfobutylether‐β‐cyclodextrin chiral stationary phases

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