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Succinimidyl (3-[(benzyloxy)carbonyl]-5-oxo-1,3-oxazolidin-4-yl)acetate on a Triazole-Bonded Phase for the Separation of Dl-Amino-Acid Enantiomers and the Mass-Spectrometric Determination of Chiral Amino Acids in Rat Plasma

Succinimidyl (3-[(benzyloxy)carbonyl]-5-oxo-1,3-oxazolidin-4-yl)acetate on a Triazole-Bonded Phase for the Separation of Dl-Amino-Acid Enantiomers and the Mass-Spectrometric Determination of Chiral Amino Acids in Rat Plasma

Tatsuya Sakamoto, Shoko Furukawa, Takuro Nishizawa, Mizuho Fukuda, Miyu Sasaki, Mayu Onozato, Shusuke Uekusa, Hideaki Ichiba, Takeshi Fukushima

J Chromatogr A. 2019 Jan 25;1585:131-137.

PMID: 30554776

Abstract:

Changes in the levels of amino-acid enantiomers are associated with some serious diseases; consequently, amino acid monitoring in peripheral blood can be used to diagnose and predict the onset of disease. Herein, we report the design and synthesis of a new chiral derivatization reagent, namely succinimidyl (4S)-(3-[(benzyloxy)carbonyl]-5-oxo-1,3-oxazolidin-4-yl)acetate ((S)-COXA-OSu), for the separation of dl-amino-acid enantiomers. The usefulness of (S)-COXA-OSu was examined as a derivatization reagent for LC-MS/MS following certification of its total optical purity (>99%). The enantiomeric separations of amino-acid derivatives tagged with the reagent were examined using a triazole-bonded phase. (S)-COXA-OSu enabled the simultaneous enantiomeric separation of more than 40 α-amino acids. (S)-COXA-amino-acid derivatives were efficiently converted into their product ions, from which formaldehyde (CH2O) was eliminated [M-30] from the oxazolidinone moiety of COXA by collision-induced dissociation during LC-MS/MS. Limits of detection were in the 0.0138-0.518 pmol/injection range. For precise and accurate quantitation, we synthesized and used a stable-isotope-labeled (S)-COXA-OSu that was used as an internal standard in LC-MS/MS-determination experiments. Finally, changes in plasma amino-acid levels in rats, following administration of S-methyl-l-cysteine, an alanine-serine-cysteine transporter-1 (Asc-1) inhibitor, were successfully detected by LC-MS/MS using (S)-COXA-OSu.

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LS7931098	3-(Benzyloxy)-6-bromo-2-fluorophenylboronic acid			Price

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