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Article

Simultaneous Analysis of d,l-Amino Acids in Human Urine Using a Chirality-Switchable Biaryl Axial Tag and Liquid Chromatography Electrospray Ionization Tandem Mass Spectrometry

1
Research Institute for Bioscience Products & Fine Chemicals, Ajinomoto Co., Inc., 1-1 Suzuki-cho, Kawasaki-ku, Kawasaki-shi 210-8681, Japan
2
R&D Planning Department, Ajinomoto Co., Inc., 1-15-1 Kyobashi, Chūō-ku, Tokyo 104-8315, Japan
*
Author to whom correspondence should be addressed.
Symmetry 2020, 12(6), 913; https://doi.org/10.3390/sym12060913
Received: 30 April 2020 / Revised: 6 May 2020 / Accepted: 11 May 2020 / Published: 2 June 2020
Although d,l-amino acids are symmetrical molecules, l-isomers are generally dominant in living organisms. However, it has been found that some d-amino acids also have biological functions. A new method for simultaneously analyzing d,l-amino acids in biological samples is required to allow unknown functions of d-amino acids to be investigated. d-Amino acids in urine are currently receiving increasing amounts of attention, particularly for screening for chronic kidney diseases. However, simultaneously analyzing d,l-amino acids in human urine is challenging because of interfering unknown compounds in urine. In this study, the axially chiral derivatizing agent (R)-4-nitrophenyl-N-[2-(diethylamino)-6,6-dimethyl-[1,1-biphenyl]-2-yl] carbamate hydrochloride was used to allow enantiomers of amino acids in human urine to be simultaneously determined by liquid chromatography electrospray ionization tandem mass spectrometry. The optimized method gave good linearities, precision results, and recoveries for 18 proteinogenic amino acids and their enantiomers and glycine. The chiral-switching method using (S)-4-nitrophenyl-N-[2-(diethylamino)-6, 6-dimethyl-[1,1-biphenyl]-2-yl]carbamate hydrochloride confirmed the expected concentrations of 32 of the 37 analytes. The method was successfully used to determine the concentrations of d-serine, d-alanine, d-asparagine, d-allothreonine, d-lysine, and the d-isomers of 10 other amino acids in five human volunteer urine samples. View Full-Text
Keywords: d-amino acid; chiral derivatization; axially chiral; urine analysis; liquid chromatography; mass spectrometry d-amino acid; chiral derivatization; axially chiral; urine analysis; liquid chromatography; mass spectrometry
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MDPI and ACS Style

Harada, M.; Karakawa, S.; Miyano, H.; Shimbo, K. Simultaneous Analysis of d,l-Amino Acids in Human Urine Using a Chirality-Switchable Biaryl Axial Tag and Liquid Chromatography Electrospray Ionization Tandem Mass Spectrometry. Symmetry 2020, 12, 913. https://doi.org/10.3390/sym12060913

AMA Style

Harada M, Karakawa S, Miyano H, Shimbo K. Simultaneous Analysis of d,l-Amino Acids in Human Urine Using a Chirality-Switchable Biaryl Axial Tag and Liquid Chromatography Electrospray Ionization Tandem Mass Spectrometry. Symmetry. 2020; 12(6):913. https://doi.org/10.3390/sym12060913

Chicago/Turabian Style

Harada, Masashi, Sachise Karakawa, Hiroshi Miyano, and Kazutaka Shimbo. 2020. "Simultaneous Analysis of d,l-Amino Acids in Human Urine Using a Chirality-Switchable Biaryl Axial Tag and Liquid Chromatography Electrospray Ionization Tandem Mass Spectrometry" Symmetry 12, no. 6: 913. https://doi.org/10.3390/sym12060913

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