Simultaneous determination of serine enantiomers in plasma
[15] M. Orozco-Ibarra, O. N. Medina-Campos, D. J. Sa´nchez-Gonza´lez,
derivatization with pentafluoropropyl chloroformate. Anal. Bioanal.
Chem. 2007, 388, 1815.
C. M. Martínez-Martínez,
E. Floriano-Sa´nchez,
A. Santamaría,
V. Ramirez, N. A. Bobadilla, J. Pedraza-Chaverri. Evaluation of
oxidative stress in D-serine induced nephrotoxicity. Toxicology
2007, 229, 123.
[27] S. A. Fuchs, M. G. M. de Sain-van der Velden, M. M. J. de Barse,
M. W. Roeleveld, M. Hendriks, L. Dorland, L. W. J. Klomp, R. Berger,
T. J. de Koning. Two mass-spectrometric techniques for quantifying
serine enantiomers and glycine in cerebrospinal fluid: potential
confounders and age-dependent ranges. Clin. Chem. 2008, 54,
1443.
[28] N. Domergue, M. Pugniere, A. Previero. One-step conversion of
amino acids into N-menthyloxycarbonyl alkyl ester derivatives for
chiral gas chromatography. Anal. Biochem. 1993, 214, 420.
[29] J. K. Whelan. Gas chromatographic confirmation of amino acid
structure via diastereomer preparation. J. Chromatogr. 1975, 111,
337.
[16] A. Hashimoto, T. Nishikawa, T. Oka, K. Takahashi, T. Hayashi.
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.
[17] A. Morikawa, K. Hamase, T. Inoue, R. Konno, A. Niwa, K. Zaitsu.
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.
[18] T. Fukushima, J. Kawai, K. Imai, T. Toyo’oka. Simultaneous
determination of D- and L-serine in rat brain microdialysis sample
usingacolumn-switchingHPLCwithfluorimetricdetection.Biomed.
Chromatogr. 2004, 18, 813.
[19] R. Sethuraman, M. G. Krishnamoorthy, T. L. Lee, E. H. C. Liu,
S. Chiang, W. Nishimura, M. Sakai, T. Minami, S. Tachibana.
Simultaneous analysis of D- and L-serine in cerebrospinal fluid
by use of HPLC. Clin. Chem. 2007, 53, 1489.
[30] M. Hasegawa, I. Matsubara. Gas chromatographic determination of
the optical purities of amino acids using N-trifluoroacetyl menthyl
esters. Anal. Biochem. 1975, 63, 308.
[31] J. Lee,K. R. Kim,S. Won,J. H. Kim,J. Goto.Enantioseparationofchiral
amino acids as the N(O, S)-ethoxycarbonylated diastereomeric
estersbyachiraldual-capillarycolumngaschromatography.Analyst
2001, 126, 2128.
[32] M. J. Paik, J. Lee, K. R. Kim. N-Ethoxycarbonylation combined with
(S)-1-phenylethylamidation for enantioseparation of amino acids
by achiral gas chromatography and gas chromatography-mass
spectrometry. J. Chromatogr. A 2008, 1214, 151.
[20] M. J. Berna, B. L. Ackermann. Quantification of serine enantiomers
in rat brain microdialysate using Marfey’s reagent and LC/MS/MS. J.
Chromatogr. B 2007, 846, 359.
[21] Y. Miyoshi, K. Hamase, Y. Tojo, M. Mita, R. Konno, K. Zaitsu. Determi-
nation 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.
[22] H. Bru¨ckner, M. Hausch. Gas chromatographic characterization of
free D-amino acids in the blood serum of patients with renal
disorders and of healthy volunteers. J. Chromatogr. 1993, 614, 7.
[23] H. Bru¨ckner, A. Schieber. Determination of amino acid enantiomers
in human urine and blood serum by gas chromatography-mass
spectrometry. Biomed. Chromatogr. 2001, 15, 166.
[24] S. Casal, M. B. Oliveira, M. A. Ferreira. Gas chromatographic
quantification of amino acid enantiomers in food matrices by
their N(O, S)-ethoxycarbonyl heptafluorobutyl ester derivatives.
J Chromatogr. A 2000, 866, 221.
[25] H. Zahradnickova, P. Husek, P. Simek. GC separation of amino
acid enantiomers via derivatization with heptafluorobutyl chloro-
formate and Chirasil-L-Val column. J. Sep. Sci. 2009, 32, 3919.
[26] H. Zahradnickova, P. Husek, P. Simek, P. Hartvich, B. Marsalek,
I. Holoubek. Determination of D- and L-amino acids produced
by cyanobacteria using gas chromatography on Chirasil-Val after
[33] M. Bertrand, A. Chabin, A. Brack, F. Westall. Separation of amino
acid enantiomers VIA chiral derivatization and non-chiral gas
chromatography. J. Chromatogr. A 2008, 1180, 131.
[34] J. A. Dale, D. L. Dull, H. S. Mosher. α-Methoxy-α-trifluoromethyl-
phenylacetic acid, a versatile reagent for the determination of
enantiomeric composition of alcohols and amines. J. Org. Chem.
1969, 34, 2543.
[35] D. E. Nichols, C. F. Barfknecht, D. B. Rusterholz, F. Benington,
R. D. Morin. Asymmetric synthesis of psychotomimetic
phenylisopropylamines. J. Med. Chem. 1973, 16, 480.
[36] J. Gal. Stereochemistry of metabolism of amphetamines: use of
(−)-α-methoxy-α-(trifluoromethyl)phenylacetyl chloride for GLC
resolution of chiral amines. J. Pharm. Sci. 1977, 66, 169.
[37] J. Gal. Mass spectra of N-[(S)-α-methoxy-α-(trifluoromethyl)phenyl-
acetyl] derivatives of chiral amines. Stereochemistry of amphet-
amine metabolism in the rat. Biol. Mass Spectrom. 1978, 5, 32.
[38] H. Hasegawa, Y. Shinohara, T. Hashimoto, R. Matsuda, Y. Hayashi.
Prediction of measurement uncertainty in isotope dilution gas
chromatography/mass spectrometry. J. Chromatogr. A 2006, 1136,
226.
c
J. Mass. Spectrom. 2011, 46, 502–507
Copyright ꢀ 2011 John Wiley & Sons, Ltd.
wileyonlinelibrary.com/journal/jms