A chiral GC–MS method for analysis of secondary amino acids after heptafluorobutyl chloroformate &amp; methylamine derivatization

Opekar, Stanislav; Zahradníčková, Helena; Vodrážka, Petr; Řimnáčová, Lucie; Šimek, Petr; Moos, Martin

doi:10.1007/s00726-021-02949-1

Cited by 9 publications

(7 citation statements)

References 41 publications

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“…An economical GC-MS analytical method based on a commercial Chirasil-L-Val capillary column was developed for secondary amino acid enantiomers and successfully applied in the analysis of chiral proline and collagen in human biofluids. 42 Supercritical Fluid Chromatography. Different from the development of novel CSPs in HPLC and GC, chiral separation by SFC mainly focuses on the establishment of efficient methods for the chiral analysis of significant compounds including bioanalytes, drugs, and pesticides with commercial chiral columns.…”

Section: ■ Chromatographymentioning

confidence: 99%

Recent Advances in Separation and Analysis of Chiral Compounds

Yan

2023

Anal. Chem.

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Section: ■ Chromatographymentioning

confidence: 99%

Recent Advances in Separation and Analysis of Chiral Compounds

Yan

2023

Anal. Chem.

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Section: Resultsmentioning

confidence: 99%

“…The accurate quantitative determination of AAs has been a long historical project with continuous improvements and innovations have been achieved. Several publications have reported AA analysis in foods and biological fluids using GC–MS, capillary electrophoresis, HILIC-MS/MS, ion-paired LC–MS/MS, electrochemical detection (CE), ion exchange chromatography, and HPLC. , Most of these methods depend on pre- or postcolumn derivatization to improve the detection sensitivity. However, elimination of derivatization steps attracts many researchers, and many studies have described the analysis of AAs without derivatization steps such as underivatized determination of free AAs in honey using LC–MS/MS, branched-chain AAs in maple syrup urine disease using LC–MS/MS, evaluation embryo viability using CE-MS, urine analysis by LC–MS/MS, ion exchange, CE-MS coupled to a porous layer-gold nanoparticle-modified chiral column, AAs and peptides in nutritive mixtures in the total parenteral nutrition solution, and online coupling of UV, fluorescence, and electrochemical detection .…”

Section: Resultsmentioning

confidence: 99%

Underivatized Amino Acid Chromatographic Separation: Optimized Conditions for HPLC-UV Simultaneous Quantification of Isoleucine, Leucine, Lysine, Threonine, Histidine, Valine, Methionine, Phenylalanine, Tryptophan, and Tyrosine in Dietary Supplements

2022

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Amino acids (AAs) are considered as the building blocks of life. Unlike nonessential AAs, the human body cannot synthesize essential AAs and should be supplied in food or dietary supplements. The aim of the work is simultaneous HPLC-UV determination of 10 structurally related AAs without pre- or postderivatization in powdered dietary supplements (PDSs). This was challenging, especially because PDS has no standardized procedures for its quality control. HPLC-UV chromatograms of the 10 AAs were recorded using a gradient elution of the mobile phase on a CLC-C18 column at 225 nm. The elution started with 100% of phosphate buffer (pH 7.4, 10 mM) for 10 min; then, the concentration of acetonitrile increased linearly to reach 50% for another 15 min at room temperature. Good separation was achieved within a 25 min run time without pre- or postderivatization. The method was carefully validated according to the ICH guidelines over the linearity range of 100–200, 50–200, 20–150, 50–400, 20–250, 75–175, 50–250, 50–250, 50–300, and 5–100 μg/mL for l -lysine, l -threonine, l -histidine, l -valine, l -methionine, l -isoleucine, l -leucine, l -tyrosine, l -phenylalanine, and l -tryptophan, respectively, with mean recoveries ranges between 98.91 and 100.77. The method was found to be precise, and the relative standard deviation (RSD) was found to be between 0.28 and 1.92 with recoveries between 97.91 and 101.11. The method was found to be robust that resists deliberate changes in pH, flow rate, and mobile-phase percentages. It was successfully applied for the analysis of PDSs. The proposed method could be very useful for the quality control of the 10 structurally related AAs during their synthesis and for testing raw materials and pharmaceutical preparations.

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“…4 Resolution of enantiomers is achievable using different techniques such as crystallization, [5][6][7] capillary electrophoresis (CE), [8][9][10] and chromatography. 11,12 Although some may prefer non-chromatographic techniques in chiral separation, sometimes using chromatographic methods is inevitable in large-scale purification. Enantioselective chromatographic techniques have been evolved rapidly, especially high-performance liquid chromatography (HPLC) based on chiral stationary phases (CSPs) has become a powerful tool for both analytical and preparative intentions.…”

Section: Introductionmentioning

confidence: 99%

“…However, it is noteworthy that the development of a chiral pharmaceutical ingredient in a racemic form can be more affordable for the pharmaceutical industry 4 . Resolution of enantiomers is achievable using different techniques such as crystallization, 5–7 capillary electrophoresis (CE), 8–10 and chromatography 11,12 . Although some may prefer non‐chromatographic techniques in chiral separation, sometimes using chromatographic methods is inevitable in large‐scale purification.…”

Section: Introductionmentioning

confidence: 99%

A new chiral stationary phase based on noscapine: Synthesis, enantioseparation, and docking study

et al. 2022

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Noscapine is an isolated compound from the opium poppy, with distinctive chiral structure and chemistry, interacts with other compounds due to having multiple π‐acceptors, hydrogen bond acceptors, and ionic sites. Therefore, it has promising applicability for the enantioselective separation of a wide range of polar, acidic, basic, and neutral compounds. A new noscapine derivative chiral stationary phase (ND‐CSP) has been synthesized by consecutive N‐demethylation, reduction, and N‐propargylation of noscapine followed by attachment of a solid epoxy‐functionalized silica bed through the 1,3‐dipolar Huisgen cycloaddition. The noscapine derivative‐based stationary phase provides a considerable surface coverage, which is greater than some commercial CSPs and can validate better enantioresolution performance. The major advantages inherent to this chiral selector are stability, reproducibility after more than 200 tests, and substantial loading capacity. The characterization by Fourier transform infrared (FTIR) spectroscopy and elemental analysis indicated successful functionalization of the silica surface. Chromatographic method conditions like flow rate and mobile phase composition for enantioseparation of various compounds such as warfarin, propranolol, mandelic acid, and a sulfanilamide derivative were optimized. Comparing the experimental results with docking data revealed a clear correlation between the calculated binding energy of ND‐CSP and each enantiomer with the resolution of enantiomer peaks.

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A chiral GC–MS method for analysis of secondary amino acids after heptafluorobutyl chloroformate & methylamine derivatization

Cited by 9 publications

References 41 publications

Recent Advances in Separation and Analysis of Chiral Compounds

Recent Advances in Separation and Analysis of Chiral Compounds

Underivatized Amino Acid Chromatographic Separation: Optimized Conditions for HPLC-UV Simultaneous Quantification of Isoleucine, Leucine, Lysine, Threonine, Histidine, Valine, Methionine, Phenylalanine, Tryptophan, and Tyrosine in Dietary Supplements

A new chiral stationary phase based on noscapine: Synthesis, enantioseparation, and docking study

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