Separation of Enantiomers of Selected Sulfur-Containing Amino Acids by Using Serially Coupled Achiral-Chiral Columns

Deáková, Zuzana; Ďuračková, Zdeňka; Armstrong, Daniel W.; Lehotay, J.

doi:10.1080/10826076.2014.968666

Cited by 10 publications

(4 citation statements)

References 12 publications

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“…Experimentally, separation of amino acids into each pure enantiomer usually requires very long chromatographic columns due to the very small differences in the interactions of each enantiomer with the chiral stationary phase. 32 Likewise, the difference in the interaction for the L-L and the L-D pairs is also expected to be small throughout the PMF profile. Specifically at the global minima (ξ = 5.5 Å) the difference amounted to only ∆∆A = 0.05 kJ/mol and at their second minima (ξ = 6.9 Å) to only ∆∆A = 0.08 kJ/mol, both much lower than k B T at T = 300 K.…”

Section: Chiral Discriminationmentioning

confidence: 99%

Themis: A Software to Assess Association Free Energies via Direct Estimative of Partition Functions

Colombari¹,

Lozada-Blanco²,

Bernardino³

et al. 2020

Preprint

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<div>We present the program <i>Themis</i> - a computer implementation of a standard statistical mechanics framework to compute free energies, average energies and entropic contributions for association processes of two atom-based structures. The partition functions are computed analytically using a discrete grid in the phase space, whose size and degree of coarseness can be controlled to allow efficient calculations and to achieve the desired level of accuracy. With this strategy, applications ranging from molecular recognition, chiral discrimination, surface adsorption and even the interactions involving molecules in electronic excited states can be handled.</div>

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Section: Chiral Discriminationmentioning

confidence: 99%

Themis: A Software to Assess Association Free Energies via Direct Estimative of Partition Functions

Colombari¹,

Lozada-Blanco²,

Bernardino³

et al. 2020

Preprint

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“…Separation was found to be influenced by both the eluent pH and the MeOH content of 0.1% TEAA (pH 4.1)/MeOH mobile phase, where a different retention mechanism was suggested to interpret the retention behavior observed at high MeOH contents. Lehotay et al [ 40 , 41 ] investigated the enantioseparation of Cys, homo-Cys, and Met as standards, and in human plasma with 2D-HPLC technique applying a Purospher C18 in the first and Chirobiotic TM T or TAG in the second dimension. Separations were optimized using RP conditions, where amino acids were separated in the first, while their enantiomers in the second dimension.…”

Section: Recent Applications Of Different Macrocyclic Antibiotic-based Cspsmentioning

confidence: 99%

Enantioselective Liquid Chromatographic Separations Using Macrocyclic Glycopeptide-Based Chiral Selectors

et al. 2021

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Numerous chemical compounds of high practical importance, such as drugs, fertilizers, and food additives are being commercialized as racemic mixtures, although in most cases only one of the isomers possesses the desirable properties. As our understanding of the biological actions of chiral compounds has improved, the investigation of the pharmacological and toxicological properties has become more and more important. Chirality has become a major issue in the pharmaceutical industry; therefore, there is a continuous demand to extend the available analytical methods for enantiomeric separations and enhance their efficiency. Direct liquid chromatography methods based on the application of chiral stationary phases have become a very sophisticated field of enantiomeric separations by now. Hundreds of chiral stationary phases have been commercialized so far. Among these, macrocyclic glycopeptide-based chiral selectors have proved to be an exceptionally useful class of chiral selectors for the separation of enantiomers of biological and pharmacological importance. This review focuses on direct liquid chromatography-based enantiomer separations, applying macrocyclic glycopeptide-based chiral selectors. Special attention is paid to the characterization of the physico-chemical properties of these macrocyclic glycopeptide antibiotics providing detailed information on their applications published recently.

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“…Lehotay's research group reported a two-dimensional HPLC-ECD method for determination of the enantiomers of Hcy, Cys, and Met using a combination of ODS and teicoplanin aglycone columns [69,70]. The chiral separation of Hcy, Cys, and Met enantiomers was realized in a single 130 min analytical run.…”

Section: Electrochemical Detectionmentioning

confidence: 99%

HPLC Analysis of Homocysteine and Related Compounds

Wada¹,

Nakamura²,

Nakashima³

2018

Non-Proteinogenic Amino Acids

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Homocysteine (Hcy), a sulfur-containing amino acid, is a representative intermediate metabolite of methionine (Met) to cysteine (Cys) via several intermediates. An elevated level of Hcy in plasma plays an important role in diseases such as neural tube defects and Down syndrome. Homocystinuria is the most common inborn error of sulfur metabolism and is caused by mutations in the metabolic enzymes of Hcy. These errors can be caused by abnormal levels of Met metabolites and classified on the basis of plasma Met levels. Additionally, Hcy and related compounds such as glutathione play an important role in maintaining homeostasis. Therefore, the simultaneous determination of Hcy and/or related compounds is required for appropriate clinical management of several diseases. The sulfur-containing amino acids and their derivatives in biological samples are quantified sensitively using high-performance liquid chromatography methods coupled with various detection methods such as UV/Vis, fluorescence, chemiluminescence, electrochemical, mass spectrometry, and tandem mass spectrometry. In this chapter, we review recent advances in these analytical methods and their applications.

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Separation of Enantiomers of Selected Sulfur-Containing Amino Acids by Using Serially Coupled Achiral-Chiral Columns

Cited by 10 publications

References 12 publications

Themis: A Software to Assess Association Free Energies via Direct Estimative of Partition Functions

Themis: A Software to Assess Association Free Energies via Direct Estimative of Partition Functions

Enantioselective Liquid Chromatographic Separations Using Macrocyclic Glycopeptide-Based Chiral Selectors

HPLC Analysis of Homocysteine and Related Compounds

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