Towards the chiral metabolomics: Liquid chromatography-mass spectrometry based dl-amino acid analysis after labeling with a new chiral reagent, (S)-2,5-dioxopyrrolidin-1-yl-1-(4,6-dimethoxy-1,3,5-triazin-2-yl)pyrrolidine-2-carboxylate, and the application to saliva of healthy volunteers

Analytica Chimica Acta

Volumn 875, Issue , 2015, Pages 73-82

  Mochizuki, Toshiki ^a   Takayama, Takahiro ^a   Todoroki, Kenichiro ^a   Inoue, Koichi ^a   Min, Jun Zhe ^a   Toyo'oka, Toshimasa ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

Author keywords

Amino acids; Chiral derivatization reagent; Chiral metabolomics; Mass spectrometry; Reversed phase chromatography; Saliva analysis

Indexed keywords

AMINES; BODY FLUIDS; CARBOXYLATION; CHROMATOGRAPHIC ANALYSIS; CHROMATOGRAPHY; COLUMN CHROMATOGRAPHY; ISOMERS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; SEPARATION; SPECTROMETRY; STEREOCHEMISTRY;

COLLISION INDUCED DISSOCIATION; DERIVATIZATION REAGENT; HIGHLY SENSITIVE DETECTIONS; LIQUID CHROMATOGRAPHY - MASS SPECTROMETRIES; METABOLOMICS; REVERSED PHASE CHROMATOGRAPHY; SALIVA ANALYSIS; SELECTED REACTION MONITORING;

AMINO ACIDS;

2,5 DIOXOPYRROLIDIN 1 YL 1 (4,6 DIMETHOXY 1,3,5 TRIAZIN 2 YL)PYRROLIDINE 2 CARBOXYLATE; ADRENALIN; ALANINE; DEXTRO ALANINE; NORADRENALIN; PROLINE; PROTON; RACEMASE; REAGENT; SERINE; TRIETHYLAMINE; UNCLASSIFIED DRUG; AMINO ACID; DICARBOXYLIC ACID; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; PYRROLIDINE DERIVATIVE; PYRROLIDINE-2,3-DICARBOXYLIC ACID;

ADULT; ALKALINITY; AMINO ACID ANALYSIS; ANALYTICAL PARAMETERS; ARTICLE; CHEMICAL LABELING; CHEMICAL PROCEDURES; COLLISIONALLY ACTIVATED DISSOCIATION; DETECTION SENSITIVITY; DIASTEREOISOMER; ENANTIOMER; FEMALE; HUMAN; HUMAN EXPERIMENT; MALE; MASS SPECTROMETRY; METABOLOMICS; PRIORITY JOURNAL; RACEMIZATION; REVERSED PHASE LIQUID CHROMATOGRAPHY; ROOM TEMPERATURE; SALIVA ANALYSIS; SALIVA LEVEL; SELECTED REACTION MONITORING; SEPARATION TECHNIQUE; SYNTHESIS; ULTRA PERFORMANCE LIQUID CHROMATOGRAPHY; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROCEDURES; REPRODUCIBILITY; SALIVA; STEREOISOMERISM; TANDEM MASS SPECTROMETRY; VALIDATION STUDY; YOUNG ADULT;

ADULT; AMINO ACIDS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DICARBOXYLIC ACIDS; FEMALE; HUMANS; INDICATORS AND REAGENTS; MALE; METABOLOMICS; PYRROLIDINES; REPRODUCIBILITY OF RESULTS; SALIVA; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STEREOISOMERISM; TANDEM MASS SPECTROMETRY; YOUNG ADULT;

EID: 84936929592     PISSN: 00032670     EISSN: 18734324     Source Type: Journal    
DOI: 10.1016/j.aca.2015.02.054     Document Type: Article

References (24)

1. Vinayavekhin N., Homan E.A., Saghatelian A. Exploring disease through metabolomics. ACS Chem. Biol. 2010, 5:91-103.
2. Gonzalez J., Willis M.S. Ivar Asbjorn Folling Discovered Phenylketonuria (PKU). Lab Med. 2010, 41(2):118-119.
3. Alvestrand A., Fürst P., Bergström J. Plasma and muscle free amino acids in uremia: influence of nutrition with amino acids. Clin. Nephrol. 1982, 18(6):297-305.
4. Fürst P. Amino acid metabolism in uremia. J. Am. Coll. Nutr. 1989, 8(4):310-323.
5. Miyoshi Y., Koga R., Oyama T., Han H., Ueno K., Masuyama K., Itoh Y., Hamase K. HPLC analysis of naturally occurring free d-amino acids in mammals. J. Pharm. Biomed. Anal. 2012, 69:42-49.
6. Snyder S.H., Kim P.M. d-amino acids as putative neurotransmitters: focus on d-serine. Neurochem. Res. 2000, 25:553-560.
7. Kleckner N.W., Dingledine R. Requirement for glycine in activation of NMDA-receptors expressed in Xenopus oocytes. Science 1988, 241:835-837.
8. Sakata K., Fukushima T., Minje L., Ogurusu T., Taira H., Mishina M., Shingai R. Modulation by l- and d-isoforms of amino acids of the l-glutamate response of N-methyl-d-aspartate receptors. Biochemistry 1999, 38:10099-10106.
9. Toyo'oka T. Determination methods for biologically active compounds by ultra-performance liquid chromatography coupled with mass spectrometry: application to the analyses of pharmaceuticals foods, plants, environments, metabonomics, and metabolomics. J. Chromatogr. Sci. 2008, 46:233-247.
10. Tsutsui H., Fujii S., Sakamoto T., Min J.Z., Todoroki K., Toyo'oka T. Chiral amines as reagents for HPLC-MS enantioseparation of chiral carboxylic acids. J. Sep. Sci. 2012, 35:1551-1559.
11. Tsutsui H., Mochizuki T., Maeda T., Noge I., Kitagawa Y., Min J.Z., Todoroki K., Inoue K., Toyo'oka T. Simultaneous determination of dl-lactic acid and dl-3-hydroxybutyric acid enantiomers in saliva of diabetes mellitus patients by high-throughput LC-ESI-MS/MS. Anal. Bioanal. Chem. 2012, 404:1925-1934.
12. Kuwabara T., Takayama T., Todoroki K., Inoue K., Min J.Z., Toyo'oka T. Evaluation of a series of prolylamidepyridines as the chiral derivatization reagents for enantioseparation of carboxylic acids by LC-ESI-MS/MS and the application to human saliva. Anal. Bioanal. Chem. 2014, 406:2641-2649.
13. Nagao R., Tsutsui H., Mochizuki T., Takayama T., Kuwabara T., Min J.Z., Inoue K., Todoroki K., Toyo'oka T. Novel chiral derivatization reagents possessing a pyridylthiourea structure for enantiospecific determination of amines and carboxylic acids in high-throughput liquid chromatography and electrospray-ionization mass spectrometry for chiral metabolomics identification. J. Chromatogr. A 2013, 1296:111-118.
14. Mochizuki T., Taniguchi S., Tsutsui H., Min J.Z., Inoue K., Todoroki K., Toyo'oka T. Relative quantification of enantiomers of chiral amines by high-throughput LC-ESI-MS/MS using isotopic variants of light and heavy l-pyroglutamic acids as the derivatization reagents. Anal. Chim. Acta 2013, 773:76-82.
15. Mochizuki T., Todoroki K., Inoue K., Min J.Z., Toyo'oka T. Isotopic variants of light and heavy l-pyroglutamic acid succinimidyl esters as the derivatization reagents for dl-amino acid chiral metabolomics identification by liquid chromatography and electrospray ionization mass spectrometry. Anal. Chim. Acta 2014, 811:51-59.
16. Shinbo K., Kubo S., Harada Y., Oonuki T., Yokokura T., Yoshida H., Amao M., Nakamura M., Kageyama N., Yamazaki J., Ozawa S., Hirayama K., Ando T., Miura J., Miyano H. Automated precolumn derivatization system for analyzing physiological amino acids by liquid chromatography/mass spectrometry. Biomed. Chromatogr. 2010, 24:683-691.
17. Shimbo K., Yahashi A., Hirayama K., Nakazawa M., Miyano H. Multifunctional and highly sensitive precolumn reagents for amino acids in liquid chromatography/tandem mass spectrometry. Anal. Chem. 2009, 81:5172-5179.
18. Chiappin S., Antonelli G., Gatti R., De Palo E.F. Saliva specimen: a new laboratory tool for diagnostic and basic investigation. Clin. Chim. Acta 2007, 383:30-40.
19. Gröschl M. Current status of salivary hormone analysis. Clin. Chem. 2008, 54:1759-1769.
20. Tanaka S., Machino M., Akita S., Yokote Y., Sakagami H. Changes in salivary amino acid composition during aging. In Vivo 2010, 24:853-856.
21. Nakamura Y., Kodama H., Satoh T., Adachi K., Watanabe S., Yokote Y., Sakagami H. During changes in salivary amino acid concentrations. In Vivo 2010, 24:837-842.
22. Pobozy E., Czarkowska W., Trojanowicz M. Determination of amino acids in saliva using capillary electrophoresis with fluorrimetric detection. J. Biochem. Biophys. Methods 2006, 67:37-47.
23. Nagata Y., Higashi M., Ishii Y., Sano H., Tanigawa M., Nagata K., Noguchi K., Urade M. The presence of high concentrations of free d-amino acids in human saliva. Life Sci. 2006, 78:1677-1681.
24. Konno R. d-Amino Acids: Practical Methods and Protocols, v.4: Enzymes Involved in the Metabolism of d-Amino Acids 2009, Nova Science Publishers.