HPLC analysis of naturally occurring free d-amino acids in mammals

Journal of Pharmaceutical and Biomedical Analysis

Volumn 69, Issue , 2012, Pages 42-49

  Miyoshi, Yurika ^a   Koga, Reiko ^a   Oyama, Tsubasa ^a   Han, Hai ^a,b   Ueno, Kyoko ^a   Masuyama, Kei ^a   Itoh, Yusuke ^a   Hamase, Kenji ^a  

^a KYUSHU UNIVERSITY   (Japan)

^b JINAN UNIVERSITY   (China)

Author keywords

Chiral analysis; D Amino acids; HPLC

Indexed keywords

DEXTRO AMINO ACID;

CHIRALITY; ENANTIOMER; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; MAMMAL; METABOLOMICS; NONHUMAN; PRIORITY JOURNAL; REVIEW; TANDEM MASS SPECTROMETRY;

AMINO ACIDS; ANIMALS; BIOLOGICAL MARKERS; BRAIN; CHEMISTRY TECHNIQUES, ANALYTICAL; CHROMATOGRAPHY; CHROMATOGRAPHY, GAS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ELECTROCHEMISTRY; HUMANS; METABOLOMICS; RATS; STEREOISOMERISM;

EID: 84865075457     PISSN: 07317085     EISSN: 1873264X     Source Type: Journal    
DOI: 10.1016/j.jpba.2012.01.041     Document Type: Review

References (61)

1. Hamase K., Morikawa A., Zaitsu K. d-Amino acids in mammals and their diagnostic value. J. Chromatogr. B 2002, 781:73-91.
2. Katane M., Homma H. d-Aspartate-an important bioactive substance in mammals: a review from an analytical and biological point of view. J. Chromatogr. B 2011, 879:3108-3121.
3. Nishikawa T. Analysis of free d-serine in mammals and its biological relevance. J. Chromatogr. B 2011, 879:3169-3183.
4. Dunlop D.S., Neidle A., McHale D., Dunlop D.M., Lajtha A. The presence of free d-aspartic acid in rodents and man. Biochem. Biophys. Res. Commun. 1986, 141:27-32.
5. Hashimoto A., Nishikawa T., Hayashi T., Fujii N., Harada K., Oka T., Takahashi K. The presence of free d-serine in rat brain. FEBS Lett. 1992, 296:33-36.
6. Hashimoto A., Nishikawa T., Oka T., Takahashi K., Hayashi T. Determination of free amino acid enantiomers in rat brain and serum by high-performance liquid chromatography after derivatization with N-tert.-butyloxycarbonyl-l-cysteine and o-phthaldialdehyde. J. Chromatogr. 1992, 582:41-48.
7. Schurig V. Gas chromatographic enantioseparation of derivatized α-amino acids on chiral stationary phases-past and present. J. Chromatogr. B 2011, 879:3122-3140.
8. Buck R.H., Krummen K. High-performance liquid chromatographic determination of enantiomeric amino acids and amino alcohols after derivatization with o-phthaldialdehyde and various chiral mercaptans; application to peptide hydrolysates. J. Chromatogr. 1987, 387:255-265.
9. Aswad D.W. Determination of d- and l-aspartate in amino acid mixtures by high-performance liquid chromatography after derivatization with a chiral adduct of o-phthaldialdehyde. Anal. Biochem. 1984, 137:405-409.
10. Buck R.H., Krummen K. Resolution of amino acid enantiomers by high-performance liquid chromatography using automated pre-column derivatisation with a chiral reagent. J. Chromatogr. 1984, 315:279-285.
11. Nimura N., Kinoshita T. o-Phthalaldehyde-N-acetyl-l-cysteine as a chiral derivatization reagent for liquid chromatographic optical resolution of amino acid enantiomers and its application to conventional amino acid analysis. J. Chromatogr. 1986, 352:169-177.
12. D'Aniello A., Cosmo A.D., Cristo C.D., Annunziato L., Petrucelli L., Fisher G. Involvement of d-aspartic acid in the synthesis of testosterone in rat testes. Life Sci. 1996, 59:97-104.
13. Kera Y., Aoyama H., Matsumura H., Hasegawa A., Nagasaki H., Yamada R. Presence of free d-glutamate and d-aspartate in rat tissues. Biochim. Biophys. Acta 1995, 1243:282-286.
14. Hashimoto A., Nishikawa T., Konno R., Niwa A., Yasumura Y., Oka T., Takahashi K. Free d-serine, d-aspartate and d-alanine in central nervous system and serum in mutant mice lacking d-amino acid oxidase. Neurosci. Lett. 1993, 152:33-36.
15. Nimura N., Fujiwara T., Watanabe A., Sekine M., Furuchi T., Yohda M., Yamagishi A., Oshima T., Homma H. A novel chiral thiol reagent for automated precolumn derivatization and high-performance liquid chromatographic enantioseparation of amino acids and its application to the aspartate racemase assay. Anal. Biochem. 2003, 315:262-269.
16. Hashimoto A., Nishikawa T., Oka T., Takahashi K. Endogenous d-serine in rat brain: N-methyl-d-aspartate receptor-related distribution and aging. J. Neurochem. 1993, 60:783-786.
17. Hashimoto A., Nishikawa T., Oka T., Hayashi T., Takahashi K. Widespread distribution of free d-aspartate in rat periphery. FEBS Lett. 1993, 331:4-8.
18. Hashimoto A., Oka T., Nishikawa T. Anatomical distribution and postnatal changes in endogenous free d-aspartate and d-serine in rat brain and periphery. Eur. J. Neurosci. 1995, 7:1657-1663.
19. Morikawa A., Hamase K., Inoue T., Konno R., Niwa A., Zaitsu K. Determination of free d-aspartic acid, d-serine and d-alanine in the brain of mutant mice lacking d-amino-acid oxidase activity. J. Chromatogr. B 2001, 757:119-125.
20. Brückner H., Haasmann S., Langer M., Westhauser T., Wittner R., Godel H. Liquid chromatographic determination of d- and l-amino acids by derivatization with o-phthaldialdehyde and chiral thiols. J. Chromatogr. A 1994, 666:259-273.
21. Marfey P. Determination of d-amino acids. II. Use of a bifunctional reagent, 1,5-difluoro-2,4-dinitrobenzene. Carlsberg Res. Commun. 1984, 49:591-596.
22. Nagata Y., Yamamoto K., Shimojo T. Determination of d- and l-amino acids in mouse kidney by high-performance liquid chromatography. J. Chromatogr. 1992, 575:147-152.
23. Einarsson S., Josefsson B., Möller P., Sanchez D. Separation of amino acid enantiomers and chiral amines using precolumn derivatization with (+)-1-(9-fluorenyl)ethyl chloroformate and reversed-phase liquid chromatography. Anal. Chem. 1987, 59:1191-1195.
24. Okuma E., Abe H. Simultaneous determination of d- and l-amino acids in the nervous tissues of crustaceans using precolumn derivatization with (+)-1-(9-fluorenyl)ethyl chloroformate and reversed-phase ion-pair high-performance liquid chromatography. J. Chromatogr. B 1994, 660:243-250.
25. Min J.Z., Hatanaka S., Yu H., Higashi T., Inagaki S., Toyo'oka T. Determination of dl-amino acids, derivatized with R(-)-4-(3-isothiocyanatopyrrolidin-1-yl)-7-(N N-dimethylaminosulfonyl)-2,1,3-benzoxadiazole, in nail of diabetic patients by UPLC-ESI-TOF-MS. J. Chromatogr. B 2011, 879:3220-3228.
26. Visser W.F., Verhoeven-Duif N.M., Ophoff R., Bakker S., Klomp L.W., Berger R., de Koning T.J. A sensitive and simple ultra-high-performance-liquid chromatography-tandem mass spectrometry based method for the quantification of d-amino acids in body fluids. J. Chromatogr. A 2011, 1218:7130-7136.
27. Imai K., Fukushima T., Hagiwara K., Santa T. Occurrence of d-aspartic acid in rat brain pineal gland. Biomed. Chromatogr. 1995, 9:106-109.
28. Imai K., Watanabe Y. Fluorimetric determination of secondary amino acids by 7-fluoro-4-nitrobenzo-2-oxa-l 3-diazole. Anal. Chim. Acta 1981, 130:377-383.
29. Ôi N., Kitahara H., Matsumoto Y., Nakajima H., Horikawa Y. (R)-N-(3, 5-Dinitrobenzoyl)-1-naphthylglycine as a chiral stationary phase for the separation of enantiomers by high-performance liquid chromatography. J. Chromatogr. 1989, 462:382-386.
30. Fukushima T., Kato M., Santa T., Imai K. Enantiomeric separation and sensitive determination of d, l-amino acids derivatized with fluorogenic benzofurazan reagents on Pirkle type stationary phases. Biomed. Chromatogr. 1995, 9:10-17.
31. Reischl R.J., Hartmanova L., Carrozzo M., Huszar M., Frühauf P., Lindner W. Chemoselective and enantioselective analysis of proteinogenic amino acids utilizing N-derivatization and 1-d enantioselective anion-exchange chromatography in combination with tandem mass spectrometric detection. J. Chromatogr. A 2011, 1218:8379-8387.
32. Mandl A., Nicoletti L., Lämmerhofer M., Lindner W. Quinine versus carbamoylated quinine-based chiral anion exchangers: a comparison regarding enantioselectivity for N-protected amino acids and other chiral acids. J. Chromatogr. A 1999, 858:1-11.
33. Armstrong D.W., Gasper M., Lee S.H., Zukowski J., Ercal N. d-Amino acid levels in human physiological fluids. Chirality 1993, 5:375-378.
34. Carpino L.A., Han G.Y. The 9-fluorenylmethoxycarbonyl amino-protecting group. J. Org. Chem. 1972, 37:3404-3409.
35. Armstrong D.W., Gasper M.P., Lee S.H., Ercal N., Zukowski J. Factors controlling the level and determination of d-amino acids in the urine and plasma of laboratory rodents. Amino Acids 1993, 5:299-315.
36. Armstrong D.W., Duncan J.D., Lee S.H. Evaluation of d-amino acid levels in human urine and in commercial l-amino acid samples. Amino Acids 1991, 1:97-106.
37. Shinbo T., Yamaguchi T., Nishimura K., Sugiura M. Chromatographic separation of racemic amino acids by use of chiral crown ether-coated reversed-phase packings. J. Chromatogr. 1987, 405:145-153.
38. Benson J.R., Hare P.E. o-Phthalaldehyde: fluorogenic detection of primary amines in the picomole range: comparison with fluorescamine and ninhydrin. Proc. Natl. Acad. Sci. USA 1975, 72:619-622.
39. Long Z., Nimura N., Adachi M., Sekine M., Hanai T., Kubo H., Homma H. Determination of d- and l-aspartate in cell culturing medium, within cells of MPT1 cell line and in rat blood by a column-switching high-performance liquid chromatographic method. J. Chromatogr. B 2001, 761:99-106.
40. Fukushima T., Kawai J., Imai K., Toyo'oka T. Simultaneous determination of d- and l-serine in rat brain microdialysis sample using a column-switching HPLC with fluorimetric detection. Biomed. Chromatogr. 2004, 18:813-819.
41. Miyoshi Y., Hamase K., Tojo Y., Mita M., Konno R., Zaitsu K. Determination of d-serine and d-alanine in the tissues and physiological fluids of mice with various d-amino-acid oxidase activities using two-dimensional high-performance liquid chromatography with fluorescence detection. J. Chromatogr. B 2009, 877:2506-2512.
42. Tojo Y., Hamase K., Konno R., Koyanagi S., Ohdo S., Zaitsu K. Simple and rapid genotyping of d-amino acid oxidase gene recognizing a crucial variant in the ddY strain using microchip electrophoresis. J. Sep. Sci. 2009, 32:430-436.
43. Ohide H., Miyoshi Y., Maruyama R., Hamase K., Konno R. d-Amino acid metabolism in mammals: biosynthesis, degradation and analytical aspects of the metabolic study. J. Chromatogr. B 2011, 879:3162-3168.
44. Yang J.H., Wada A., Yoshida K., Miyoshi Y., Sayano T., Esaki K., Kinoshita M.O., Tomonaga S., Azuma N., Watanabe M., Hamase K., Zaitsu K., Machida T., Messing A., Itohara S., Hirabayashi Y., Furuya S. Brain-specific Phgdh deletion reveals a pivotal role for l-serine biosynthesis in controlling the level of d-serine, an N-methyl-d-aspartate receptor co-agonist, in adult brain. J. Biol. Chem. 2010, 285:41380-41390.
45. Sasabe J., Miyoshi Y., Suzuki M., Mita M., Konno R., Matsuoka M., Hamase K.S. Aiso, d-Amino acid oxidase controls motoneuron degeneration through d-serine, Proc. Natl. Acad. Sci. U. S. A. 2012, 109:627-632.
46. Kakegawa W., Miyoshi Y., Hamase K., Matsuda S., Matsuda K., Kohda K., Emi K., Motohashi J., Konno R., Zaitsu K., Yuzaki M. d-Serine regulates cerebellar LTD and motor coordination through the δ2 glutamate receptor. Nat. Neurosci. 2011, 14:603-611.
47. Morikawa A., Hamase K., Zaitsu K. Determination of d-alanine in the rat central nervous system and periphery using column-switching high-performance liquid chromatography. Anal. Biochem. 2003, 312:66-72.
48. Etoh S., Hamase K., Morikawa A., Ohgusu T., Zaitsu K. Enantioselective visualization of d-alanine in rat anterior pituitary gland: localization to ACTH-secreting cells. Anal. Bioanal. Chem. 2009, 393:217-223.
49. Morikawa A., Hamase K., Ohgusu T., Etoh S., Tanaka H., Koshiishi I., Shoyama Y., Zaitsu K. Immunohistochemical localization of d-alanine to β-cells in rat pancreas. Biochem. Biophys. Res. Commun. 2007, 355:872-876.
50. Morikawa A., Hamase K., Miyoshi Y., Koyanagi S., Ohdo S., Zaitsu K. Circadian changes of d-alanine and related compounds in rats and the effect of restricted feeding on their amounts. J. Chromatogr. B 2008, 875:168-173.
51. Inoue T., Hamase K., Morikawa A., Zaitsu K. Determination of minute amounts of d-leucine in various brain regions of rat and mouse using column-switching high-performance liquid chromatography. J. Chromatogr. B 2000, 744:213-219.
52. Hamase K., Inoue T., Morikawa A., Konno R., Zaitsu K. Determination of free d-proline and d-leucine in the brains of mutant mice lacking d-amino acid oxidase activity. Anal. Biochem. 2001, 298:253-258.
53. Hamase K., Takagi S., Morikawa A., Konno R., Niwa A., Zaitsu K. Presence and origin of large amounts of d-proline in the urine of mutant mice lacking d-amino acid oxidase activity. Anal. Bioanal. Chem. 2006, 386:705-711.
54. Han H., Miyoshi Y., Ueno K., Okamura C., Tojo Y., Mita M., Lindner W., Zaitsu K., Hamase K. Simultaneous determination of d-aspartic acid and d-glutamic acid in rat tissues and physiological fluids using a multi-loop two-dimensional HPLC procedure. J. Chromatogr. B 2011, 879:3196-3202.
55. Hamase K., Homma H., Takigawa Y., Fukushima T., Santa T., Imai K. Regional distribution and postnatal changes of d-amino acids in rat brain. Biochim. Biophys. Acta 1997, 1334:214-222.
56. Snyder S.H., Kim P.M. d-Amino acids as putative neurotransmitters: focus on d-serine. Neurochem. Res. 2000, 25:553-560.
57. Kleckner N.W., Dingledine R. Requirement for glycine in activation of NMDA-receptors expressed in Xenopus oocytes. Science 1998, 241:835-837.
58. Miyoshi Y., Hamase K., Okamura T., Konno R., Kasai N., Tojo Y., Zaitsu K. Simultaneous two-dimensional HPLC determination of free d-serine and d-alanine in the brain and periphery of mutant rats lacking d-amino-acid oxidase. J. Chromatogr. B 2011, 879:3184-3189.
59. Tojo Y., Hamase K., Nakata M., Morikawa A., Mita M., Ashida Y., Lindner W., Zaitsu K. Automated and simultaneous two-dimensional micro-high-performance liquid chromatographic determination of proline and hydroxyproline enantiomers in mammals. J. Chromatogr. B 2008, 875:174-179.
60. Hamase K., Morikawa A., Ohgusu T., Lindner W., Zaitsu K. Comprehensive analysis of branched aliphatic d-amino acids in mammals using an integrated multi-loop two-dimensional column-switching high-performance liquid chromatographic system combining reversed-phase and enantioselective columns. J. Chromatogr. A 2007, 1143:105-111.
61. Hamase K., Miyoshi Y., Ueno K., Han H., Hirano J., Morikawa A., Mita M., Kaneko T., Lindner W., Zaitsu K. Simultaneous determination of hydrophilic amino acid enantiomers in mammalian tissues and physiological fluids applying a fully automated micro-two-dimensional high-performance liquid chromatographic concept. J. Chromatogr. A 2010, 1217:1056-1062.