Extra-facile chiral separation of amino acid enantiomers by LC-TOFMS analysis

Konya, Yutaka; Bamba, Takeshi; Fukusaki, Eiichiro

doi:10.1016/j.jbiosc.2015.06.017

Cited by 35 publications

(18 citation statements)

References 7 publications

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“…Thus, constant eluent composition is an important issue for the quantitative determination of enantiomeric purity. A relatively fast isocratic RP HPLC-MS method was developed for chiral separations of underivatized α-amino acids on a CROWNPAK CR-I (+) column (Daicel, Corp., Osaka, Japan) [ 31 ]. In a subsequent report of the authors, the LC-MS method was further developed and applied for the analysis of amino acids in black vinegar [ 32 ].…”

Section: Recent Applications Of Crown Ether-based Cspsmentioning

confidence: 99%

Liquid Chromatographic Enantioseparations Utilizing Chiral Stationary Phases Based on Crown Ethers and Cyclofructans

et al. 2021

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Natural compounds can exist in different forms, where molecules possessing chirality play an essential role in living organisms. Currently, one of the most important tasks of modern analytical chemistry is the enantioseparation of chiral compounds, in particular, the enantiomers of compounds having biological and/or pharmaceutical activity. Whether the task is to analyze environmental or food samples or to develop an assay for drug control, well-reproducible, highly sensitive, stereoselective, and robust methods are required. High-performance liquid chromatography best meets these conditions. Nevertheless, in many cases, gas chromatography, supercritical fluid chromatography, or capillary electrophoresis can also offer a suitable solution. Amino acids, proteins, cyclodextrins, derivatized polysaccharides, macrocyclic glycopeptides, and ion exchangers can serve as efficient selectors in liquid chromatography, and they are quite frequently applied and reviewed. Crown ethers and cyclofructans possessing similar structural characteristics and selectivity in the enantiodiscrimination of different amine compounds are discussed less frequently. This review collects information on enantioseparations achieved recently with the use of chiral stationary phases based on crown ethers or cyclofructans, focusing on liquid chromatographic applications.

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Section: Recent Applications Of Crown Ether-based Cspsmentioning

confidence: 99%

Liquid Chromatographic Enantioseparations Utilizing Chiral Stationary Phases Based on Crown Ethers and Cyclofructans

et al. 2021

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“…D -Amino acids can be assayed using ultra-performance liquid chromatography ( Ohmori et al, 2011 ), gas chromatography-mass spectrometry ( Schurig, 2011 ), and liquid chromatography-tandem mass spectrometry ( Konya et al, 2016 ). These methods are useful for simultaneous analysis of numerous kinds of D -amino acids.…”

Section: Spectrophotometric Assay Of D -Isoleucinementioning

confidence: 99%

Artificial Thermostable D-Amino Acid Dehydrogenase: Creation and Application

et al. 2018

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Many kinds of NAD(P)+-dependent L-amino acid dehydrogenases have been so far found and effectively used for synthesis of L-amino acids and their analogs, and for their sensing. By contrast, similar biotechnological use of D-amino acid dehydrogenase (D-AADH) has not been achieved because useful D-AADH has not been found from natural resources. Recently, using protein engineering methods, an NADP+-dependent D-AADH was created from meso-diaminopimelate dehydrogenase (meso-DAPDH). The artificially created D-AADH catalyzed the reversible NADP+-dependent oxidative deamination of D-amino acids to 2-oxo acids. The enzyme, especially thermostable one from thermophiles, was efficiently applicable to synthesis of D-branched-chain amino acids (D-BCAAs), with high yields and optical purity, and was useful for the practical synthesis of 13C- and/or 15N-labeled D-BCAAs. The enzyme also made it possible to assay D-isoleucine selectively in a mixture of isoleucine isomers. Analyses of the three-dimensional structures of meso-DAPDH and D-AADH, and designed mutations based on the information obtained made it possible to markedly enhance enzyme activity and to create D-AADH homologs with desired reactivity profiles. The methods described here may be an effective approach to artificial creation of biotechnologically useful enzymes.

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“…Thus, it is essential to obtain pure enantiomers of the building blocks for proteins and peptides for their therapeutic or diagnostic applications. Several HPLC methods have been applied with different chiral selectors for chiral separation of the primary, secondary as well as beta and gamma amino acids [ 107 , 109 , 110 ]. Baseline and partial enantioseparation of some amino acids by modified CNTs have been reported and discussed in the following sections.…”

Section: Swcnts and Mwcnts For Chiral Separation In Biological Actmentioning

confidence: 99%

Application of Carbon Nanotubes in Chiral and Achiral Separations of Pharmaceuticals, Biologics and Chemicals

et al. 2017

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Carbon nanotubes (CNTs) possess unique mechanical, physical, electrical and absorbability properties coupled with their nanometer dimensional scale that renders them extremely valuable for applications in many fields including nanotechnology and chromatographic separation. The aim of this review is to provide an updated overview about the applications of CNTs in chiral and achiral separations of pharmaceuticals, biologics and chemicals. Chiral single-walled carbon nanotubes (SWCNTs) and multi-walled carbon nanotubes (MWCNTs) have been directly applied for the enantioseparation of pharmaceuticals and biologicals by using them as stationary or pseudostationary phases in chromatographic separation techniques such as high-performance liquid chromatography (HPLC), capillary electrophoresis (CE) and gas chromatography (GC). Achiral MWCNTs have been used for achiral separations as efficient sorbent objects in solid-phase extraction techniques of biochemicals and drugs. Achiral SWCNTs have been applied in achiral separation of biological samples. Achiral SWCNTs and MWCNTs have been also successfully used to separate achiral mixtures of pharmaceuticals and chemicals. Collectively, functionalized CNTs have been indirectly applied in separation science by enhancing the enantioseparation of different chiral selectors whereas non-functionalized CNTs have shown efficient capabilities for chiral separations by using techniques such as encapsulation or immobilization in polymer monolithic columns.

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Extra-facile chiral separation of amino acid enantiomers by LC-TOFMS analysis

Cited by 35 publications

References 7 publications

Liquid Chromatographic Enantioseparations Utilizing Chiral Stationary Phases Based on Crown Ethers and Cyclofructans

Liquid Chromatographic Enantioseparations Utilizing Chiral Stationary Phases Based on Crown Ethers and Cyclofructans

Artificial Thermostable D-Amino Acid Dehydrogenase: Creation and Application

Application of Carbon Nanotubes in Chiral and Achiral Separations of Pharmaceuticals, Biologics and Chemicals

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