Chiral separation of intact amino acids by capillary electrophoresis-mass spectrometry employing a partial filling technique with a crown ether carboxylic acid

Journal of Chromatography A - Tập 1586 - Trang 128-138 - 2019
Sul Lee1,2, Su-Jin Kim1,3, Eunjung Bang1, Yun-Cheol Na1,2
1Western Seoul Center, Korea Basic Science Institute, 150 Bugahyeon-ro, Seodaemun-gu, Seoul, 03759, Republic of Korea
2Department of Chemistry and Nano Science, Ewha Womans University, 52 Ewhayeodae-gil, Seodaemun-gu, Seoul 03760, Republic of Korea
3Department of Food Science & Engineering, Ewha Womans University, 52 Ewhayeodae-gil, Seodaemun-gu, Seoul 03760, Republic of Korea

Tài liệu tham khảo

Chervyakov, 2011, D-amino acids in normal ageing and pathogenesis of neurodegenerative diseases, Neurochem. J., 5, 100, 10.1134/S1819712411020036 Fujii, 2011, d-Amino acids in aged proteins: analysis and biological relevance, J. Chromatogr. B, 879, 3141, 10.1016/j.jchromb.2011.05.051 Sasabe, 2014, Ischemic acute kidney injury perturbs homeostasis of serine enantiomers in the body fluid in mice: early detection of renal dysfunction using the ratio of serine enantiomers, PLoS One, 9, 10.1371/journal.pone.0086504 Kimura, 2016, Chiral amino acid metabolomics for novel biomarker screening in the prognosis of chronic kidney disease, Sci. Rep., 6, 26137, 10.1038/srep26137 Sievers, 2011, Structure-based design of non-natural amino-acid inhibitors of amyloid fibril formation, Nature, 475, 96, 10.1038/nature10154 Samakashvili, 2011, Analysis of chiral amino acids in cerebrospinal fluid samples linked to different stages of Alzheimer disease, Electrophoresis, 32, 2757, 10.1002/elps.201100139 Oliet, 2009, Regulation of N-methyl-D-aspartate receptors by astrocytic D-serine, Neuroscience, 158, 275, 10.1016/j.neuroscience.2008.01.071 Henneberger, 2010, Long-term potentiation depends on release of D-serine from astrocytes, Nature, 463, 232, 10.1038/nature08673 Brückner, 1989, Gas chromatographic detection of d-amino acids as common constituents of fermented foods, Chromatographia, 28, 487, 10.1007/BF02261066 Friedman, 1999, Chemistry, nutrition, and microbiology of D-amino acids, J. Agric. Food Chem., 47, 3457, 10.1021/jf990080u Mutaguchi, 2013, Distribution of D-amino acids in vinegars and involvement of lactic acid bacteria in the production of D-amino acids, SpringerPlus, 2, 691, 10.1186/2193-1801-2-691 Brückner, 1993, Chirality of amino acids of microorganisms used in food biotechnology, Chirality, 5, 385, 10.1002/chir.530050521 Schiffman, 1981, Comparison of taste qualities and thresholds of D-and L-amino acids, Physiol. Behav., 27, 51, 10.1016/0031-9384(81)90298-5 Kawai, 2012, Gustatory sensation of L-and D-amino acids in humans, Amino Acids, 43, 2349, 10.1007/s00726-012-1315-x Okada, 2013, Principal component analysis of the relationship between the D-amino acid concentrations and the taste of the sake, Amino Acids, 44, 489, 10.1007/s00726-012-1359-y Sardella, 2013, Combined monodimensional chromatographic approaches to monitor the presence of D-amino acids in cheese, Food Control, 34, 478, 10.1016/j.foodcont.2013.05.026 Rocco, 2013, Chiral separations in food analysis, Trac Trends Anal. Chem., 52, 206, 10.1016/j.trac.2013.05.022 Tesařová, 2000, Enantioseparation of selected N-tert.-Butyloxycarbonyl amino acids in high-performance liquid chromatography and capillary electrophoresis with a teicoplanin chiral selector, J. Chromatogr. A, 879, 147, 10.1016/S0021-9673(00)00382-4 Levkin, 2006, Combining the enantioselectivities of L-valine diamide and permethylated β-cyclodextrin in one gas chromatographic chiral stationary phase, Anal. Chem., 78, 5143, 10.1021/ac0606148 Schurig, 2011, Gas chromatographic enantioseparation of derivatized α-amino acids on chiral stationary phases—past and present, J. Chromatogr. B, 879, 3122, 10.1016/j.jchromb.2011.04.005 Hyun, 1998, Liquid chromatographic resolution of racemic amino acids and their derivatives on a new chiral stationary phase based on crown ether, J. Chromatogr. A, 822, 155, 10.1016/S0021-9673(98)00606-2 Konya, 2016, Extra-facile chiral separation of amino acid enantiomers by LC-TOFMS analysis, J. Biosci. Bioeng., 121, 349, 10.1016/j.jbiosc.2015.06.017 Armstrong, 1994, Use of a macrocyclic antibiotic as the chiral selector for enantiomeric separations by TLC, J. Liq. Chromatogr. Relat. Technol., 17, 1695, 10.1080/10826079408013451 Lee, 2017, Saturated fatty acid determination method using paired ion electrospray ionization mass spectrometry coupled with capillary electrophoresis, Anal. Chim. Acta, 984, 223, 10.1016/j.aca.2017.06.052 Prior, 2016, Enantioselective capillary electrophoresis-mass spectrometry of amino acids in cerebrospinal fluid using a chiral derivatizing agent and volatile surfactant, Anal. Chim. Acta, 940, 150, 10.1016/j.aca.2016.08.040 Moldovan, 2016, A micellar electrokinetic chromatography–mass spectrometry approach using in-capillary diastereomeric derivatization for fully automatized chiral analysis of amino acids, J. Chromatogr. A, 1467, 400, 10.1016/j.chroma.2016.08.035 Prior, 2018, Enantioselective micellar electrokinetic chromatography of dl‐amino acids using (+)‐1‐(9‐fluorenyl)‐ethyl chloroformate derivatization and UV‐induced fluorescence detection, J. Sep. Sci., 10.1002/jssc.201800204 Fradi, 2014, In-capillary derivatization with (−)-1-(9-fluorenyl) ethyl chloroformate as chiral labeling agent for the electrophoretic separation of amino acids, J. Chromatogr. A, 1363, 338, 10.1016/j.chroma.2014.07.022 Prior, 2018, Chiral capillary electrophoresis with UV-excited fluorescence detection for the enantioselective analysis of 9-fluorenylmethoxycarbonyl-derivatized amino acids, Anal. Bioanal. Chem., 1 Prior, 2016, Enantioselective analysis of proteinogenic amino acids in cerebrospinal fluid by capillary electrophoresis–mass spectrometry, Electrophoresis, 37, 2410, 10.1002/elps.201600015 Blanco, 2003, Choice of chiral selector for enantioseparation by capillary electrophoresis, Trac Trends Anal. Chem., 22, 428, 10.1016/S0165-9936(03)00705-2 Kuhn, 1992, Chiral recognition and enantiomeric resolution based on host-guest complexation with crown ethers in capillary zone electrophoresis, Anal. Chem., 64, 2815, 10.1021/ac00046a026 Salami, 2005, Capillary electrophoretic separation of enantiomers of amino acids and amino acid derivatives using crown ether and cyclodextrin, Die Pharmazie Int. J. Pharm. Sci., 60, 181 Underberg, 2002, Derivatization trends in capillary electrophoresis: an update, Electrophoresis, 23, 3922, 10.1002/elps.200290010 Schultz, 2003, Analysis of underivatized amino acids and their D/L-enantiomers by sheathless capillary electrophoresis/electrospray ionization-mass spectrometry, Anal. Chem., 75, 1508, 10.1021/ac0263925 Moini, 2003, CE/electrospray ionization-MS analysis of underivatized d/l-amino acids and several small neurotransmitters at attomole levels through the use of 18-crown-6-tetracarboxylic acid as a complexation reagent/background electrolyte, Anal. Chem., 75, 6282, 10.1021/ac034708i Hyun, 2001, New chiral crown ether stationary phase for the liquid chromatographic resolution of α-amino acid enantiomers, J. Chromatogr. A, 910, 359, 10.1016/S0021-9673(00)01230-9 Yu Jin, 2006, Development of the antipode of the covalently bonded crown ether type chiral stationary phase for the advantage of the reversal of elution order, J. Liq. Chromatogr. Relat. Technol., 29, 841, 10.1080/10826070500531102 Bang, 2001, Chiral recognition of (18-crown-6)-tetracarboxylic acid as a chiral selector determined by NMR spectroscopy, Journal of the Chemical Society, J. Chem. Soc. Perkin Trans. I, 2, 1685, 10.1039/b102026i Giuffrida, 2014, Recent advances in chiral separation of amino acids using capillary electromigration techniques, J. Chromatogr. A, 1363, 41, 10.1016/j.chroma.2014.08.041