A novel approach for LC-MS/MS-based chiral metabolomics fingerprinting and chiral metabolomics extraction using a pair of enantiomers of chiral derivatization reagents

Analytica Chimica Acta

Volumn 898, Issue , 2015, Pages 73-84

  Takayama, Takahiro ^a   Mochizuki, Toshiki ^a   Todoroki, Kenichiro ^a   Min, Jun Zhe ^a   Mizuno, Hajime ^a   Inoue, Koichi ^b   Akatsu, Hiroyasu ^c   Noge, Ichiro ^d   Toyo'oka, Toshimasa ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

^b RITSUMEIKAN UNIVERSITY   (Japan)

^c NAGOYA CITY UNIVERSITY GRADUATE SCHOOL OF MEDICAL SCIENCES   (Japan)

^d Numazu City Hospital   (Japan)

Author keywords

Alzheimer's disease; Chiral derivatization reagent; Chiral metabolomics; Diabetes mellitus; Reversed phase chromatography; Tandem mass spectrometry

Indexed keywords

AMINES; AMINO ACIDS; BIOMARKERS; BIOMOLECULES; DIAGNOSIS; ENANTIOMERS; EXTRACTION; ION CHROMATOGRAPHY; LACTIC ACID; MASS SPECTROMETRY; MULTIVARIANT ANALYSIS; NEURODEGENERATIVE DISEASES; PHYSICOCHEMICAL PROPERTIES; REAGENTS;

ALZHEIMER'S DISEASE; DERIVATIZATION REAGENT; DIABETES MELLITUS; METABOLOMICS; REVERSED PHASE CHROMATOGRAPHY; TANDEM MASS SPECTROMETRY;

METABOLITES;

AMINE; CARBOXYL GROUP; LACTIC ACID; PHENYLALANINE; REAGENT; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS;

ALZHEIMER DISEASE; ARTICLE; BRAIN HOMOGENATE; CHIRAL METABOLOMICS EXTRACTION; CHIRAL METABOLOMICS FINGERPRINTING; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; DERIVATIZATION; DIABETES MELLITUS; ENANTIOMER; EXTRACTION; HUMAN; HUMAN TISSUE; INVESTIGATIVE PROCEDURES; MASS SPECTROMETRY; METABOLOMICS; MULTIVARIATE ANALYSIS; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; SALIVA; ULTRA PERFORMANCE LIQUID CHROMATOGRAPHY; CHEMISTRY; LIQUID CHROMATOGRAPHY; PROCEDURES; STEREOISOMERISM; TANDEM MASS SPECTROMETRY;

AMINES; CHROMATOGRAPHY, LIQUID; INDICATORS AND REAGENTS; METABOLOMICS; STEREOISOMERISM; TANDEM MASS SPECTROMETRY;

EID: 84945942427     PISSN: 00032670     EISSN: 18734324     Source Type: Journal    
DOI: 10.1016/j.aca.2015.10.010     Document Type: Article

References (20)

1. Inoue K., Tsuchiya H., Takayama T., Akatsu H., Hashizume Y., Yamamoto T., Matsukawa N., Toyo'oka T. Blood-based diagnosis of Alzheimer's disease using fingerprintingmetabolomics based on hydrophilic interaction liquid chromatography with mass spectrometry and multivariatestatistical analysis. J. Chromatogr. B 2015, 974:24-34.
2. Nishiumi S., Kobayashi T., Ikeda A., Yoshie T., Kibi M., Izumi Y., Okuno T., Hayashi N., Kawano S., Takenawa T., Azuma T., Yoshida M. A novel serum metabolomics-based diagnostic approach for colorectal cancer. PLoS One 2012, 7(7):e40459.
3. Nishiumi S., Shinohara M., Ikeda A., Yoshie T., Hatano N., Kakuyama S., Mizuno S., Sanuki T., Kutsumi H., Fukusaki E., Azuma T., Takenawa T., Yoshida M. Serum metabolomics as a novel diagnostic approach for pancreatic cancer. Metabolomics 2010, 6:518-528.
4. Vinayavekhin N., Homan E.A., Saghatelian A. Exploring disease through metabolomics. ACS Chem. Biol. 2010, 5:91-103.
5. Gonzalez J., Willis M.S. Ivar Asbjorn Folling discovered Phenylketonuria (PKU). Lab. Med. 2010, 41(2):118-119.
6. 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.
7. Fürst P. Amino acid metabolism in uremia. J. Am. Coll. Nutr. 1989, 8(4):310-323.
8. 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.
9. Snyder S.H., Kim P.M. D-amino acids as putative neurotransmitters: focus on D-serine. Neurochem. Res. 2000, 25:553-560.
10. Kleckner N.W., Dingledine R. Requirement for glycine in activation of NMDA-receptors expressed in Xenopus oocytes. Science 1988, 241:835-837.
11. 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.
12. 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.
13. 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.
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. Mochizuki T., Takayama T., Todoroki K., Inoue K., Min J.Z., Toyo'oka T. 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. Anal. Chim. Acta 2015, 875:73-82.
17. 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.
18. 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.
19. 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.
20. Takayama T., Kuwabara T., Maeda T., Noge I., Kitagawa Y., Inoue K., Todoroki K., Min J.Z., Toyo'oka T. Profiling of chiral and achiral carboxylic acid metabolomics: Synthesis and evaluation of triazine-type chiral derivatization reagents for carboxylic acids by LC-ESI-MS/MS and the application to saliva of healthy volunteers and diabetic patients. Anal. Bioanal. Chem. 2015, 407:1003-1014.