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

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

doi:10.1016/j.chroma.2018.11.061

Cited by 15 publications

(14 citation statements)

References 29 publications

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“…Several diastereomer derivatization reagents reported previously for amino compounds have an optically active five‐membered ring in their structures (Figure S4). For example, DBD–PyNCS and NBD–PyNCS have a chiral pyrrolidine moiety, while succinimidyl {3‐[(benzyloxy)carbonyl]‐5‐oxo‐1,3‐oxazolidin‐4‐yl}acetate (Sakamoto et al, 2019) has a chiral oxazolidinone moiety. A chiral Pro is often used for diastereomer derivatization reagents such as 4‐(2‐chloroformylpyrrolidin‐1‐yl)‐7‐( N , N ‐dimethylaminosulfonyl)‐2,1,3‐benzoxadiazole (Toyo'oka et al, 1994b; Toyo'oka, Liu, Hanioka, Jinno, & Ando, 1994), 4‐(2‐chloroformylpyrrolidin‐1‐yl)‐7‐nitro‐2,1,3‐benzoxadiazole (Toyo'oka et al, 1994a) and N ‐[4‐(6‐methoxy‐2‐benzoxazolyl)]benzoyl‐L‐proline (Kondo et al, 1994; Figure S4).…”

Section: Resultsmentioning

confidence: 99%

Fluorimetric determination of the enantiomers of vigabatrin, an antiepileptic drug, by reversed‐phase HPLC with a novel diastereomer derivatization reagent

Uekusa

Onozato

Sakamoto

et al. 2021

Biomedical Chromatography

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Herein, determination of an antiepileptic drug, (±)‐vigabatrin (VB), was performed by reversed‐phase HPLC with fluorimetric detection using a newly designed and synthesized fluorescence derivatization reagent, 2,5‐dioxopyrrolidin‐1‐yl (4‐{[(2‐nitrophenyl)sulfonyl]oxy}‐6‐(3‐oxomorpholino)quinoline‐2‐carbonyl)prolinate [Ns‐MOK‐(R)‐ or (S)‐Pro‐OSu]. During the derivatization of VB with Ns‐MOK‐(R)‐Pro‐OSu at 60°C, the nosyl (Ns) group, which was introduced to protect a phenolic hydroxy group, was released within 30 min to produce MOK‐(R)‐Pro‐VB, which was detected fluorimetrically at 448 nm with an excitation wavelength of 333 nm. The VB enantiomers were separated on an octadecylsilica (ODS) column with a resolution value of 5.57, because Ns‐MOK‐(R)‐Pro‐OSu bears an optically active D‐proline structure. A complete separation of MOK‐(R)‐Pro‐(R)‐ and ‐(S)‐VB enantiomers was achieved on the ODS column within 40 min using stepwise gradient elution, and the detection limits were ~0.80 and 0.37 pmol on the column, respectively. The proposed HPLC with fluorimetric detection method was successfully used for determining VB enantiomers in VB‐spiked human serum following solid‐phase extraction with an anion‐exchange cartridge.

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Section: Resultsmentioning

confidence: 99%

Fluorimetric determination of the enantiomers of vigabatrin, an antiepileptic drug, by reversed‐phase HPLC with a novel diastereomer derivatization reagent

Uekusa

Onozato

Sakamoto

et al. 2021

Biomedical Chromatography

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“…Commonly, hydrophilic interaction chromatography (HILIC) column is widely used to analyze amino acids [18,23,[26][27][28]. HILIC column has hydrophilic polar stationary phase which can interact with highly polar compounds by strong hydrophilic interaction [18].…”

Section: Discussionmentioning

confidence: 99%

Simultaneous determination of five essential amino acids in plasma of Hyperlipidemic subjects by UPLC-MS/MS

Chen

Lin

et al. 2020

Lipids Health Dis

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Background: Millions of adults have been reported with hyperlipemia in the world. It is still unclear whether the plasma level of essential amino acids (AAs) will be influenced by the hyperlipemia. This study was aimed to investigate the AAs levels and the underlying metabolic relationship in hyperlipidemic subjects. Methods: An ultra-high performance liquid chromatography-tandem mass spectrometric (UPLC-MS/MS) method was developed for the determination of phenylalanine (Phe), valine (Val), histidine (His), tryptophan (Trp), and methionine (Met). Plasma samples (100 μL) were precipitated by acetonitrile (300 μL) and analyzed on a BEH C18 (2.1 mm × 100 mm, 1.7 μm) column at 40°C by gradient elution. The mobile phase composed of 0.1% formic acid and acetonitrile was used with flow rate at 0.2-0.4 ml/0-3 min. Five AAs were determined at positive electrospray ionization (ESI+) at m/z 118.1/72.1 (Val), 150.12/104.02(Met), 156.06/110.05(His), 166.1/120.1(Phe), and 205.2/188.02 (Trp). A total of 75 healthy subjects and 83 hyperlipidemic subjects, who had blood routine test and plasma lipid test were determined by developed UPLC-MS/MS. Results: It was shown that there was good linearity for Val, Met, His, Phe, and Trp within 1-100 μg/mL. The relative standard deviations of precision and accuracy were all within 15%. The level of Val, Phe, Trp, His, and Met were 35.34 ± 15.64, 22.72 ± 9.13, 17.23 ± 4.94, 16.78 ± 13.64, and 6.24 ± 1.97 μg/mL in healthy subjects, while they were 38. 04 ± 16.70, 22.41 ± 8.45, 15.62 ± 5.77, 18.35 ± 14.49, and 6.21 ± 1.97 μg/mL in hyperlipidemic subjects respectively. The Spearman's correlations analysis showed that there were high correlations between Val, Phe, Trp, His, Met and triglyceride in healthy subjects. While, those correlations decreased in hyperlipemia cases. Conclusion: A convenient and sensitive method for simultaneous determination of Val, Phe, Trp, His, and Met in human plasma was developed. There was a high correlation between Val, Phe, Trp, His, Met and triglyceride. Hyperlipemia influences the metabolic balance of His, Phe, Trp, Met and Val.

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“…. Very recently, Sakamoto et al (2019) reported another diastereomeric ICD, 2 H 0 / 2 H 5 -succinimidyl (4S)- respectively. This method was applied for monitoring the changes in amino-acid levels in rat plasma after administration of the alanine-serine-cysteine transporter-1 (Asc-1) inhibitor S-methyl-L-cysteine.…”

Section: N-hydroxysuccinimidyl Estersmentioning

confidence: 99%

“…Moreover, chiral metabolites could be easily quantified using the SIPAL strategy even in complex biological samples (Zhang et al, ). Very recently, Sakamoto et al () reported another diastereomeric ICD, 2 H 0 / 2 H 5 ‐succinimidyl (4 S )‐(3‐[(benzyloxy)‐carbonyl]‐5‐oxo‐1,3‐oxazolidin‐4‐yl)acetate [ 2 H 0 / 2 H 5 ‐( S )‐COXA‐NHS], for the chiral separation of D/L‐amino acid. 2 H 5 ‐( S )‐COXA‐NHS was synthesized using 2 H 3 ‐L‐Asp and 2 H 2 ‐paraformaldehyde instead of their unlabeled forms that were used in the 2 H 0 ‐( S )‐COXA‐NHS synthesis.…”

Section: Isotope‐coded Derivatization Reagents For Lc–ms Analysismentioning

confidence: 99%

Current trends in isotope‐coded derivatization liquid chromatographic‐mass spectrometric analyses with special emphasis on their biomedical application

El-Maghrabey

Kishikawa

Kuroda

2020

Biomedical Chromatography

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Currently, LC–MS has various applications in different areas such as metabolomics, pharmacokinetics, and pathological studies. Yet, matrix effects resulting from co‐existing constituents remain a major problem for LC–MS [or LC–tandem mass spectrometry (LC–MS/MS)]. Moreover, technical problems and instrumental drifts may lead to ion abundance variance. Thus, an internal standard (IS) is required to guarantee the accuracy and precision of the method. Because of their limited number, isotope‐coded derivatization (ICD) has been recently introduced to overcome this problem. For ICD, a stable heavy isotope‐coded moiety is used for labeling the standard or the control sample and the formed products can act as ISs. A light form of the reagent is used for labeling the sample. Then, both are mixed and analyzed by LC–MS(/MS). This strategy permits the identification of different unknown analytes including potential metabolites and disease biomarkers. All these attributes lead to persistent growth in the applications of ICD LC–MS(/MS) in various biomedical branches. In this article we review the ICD methods published in the last eight years for biomedical applications as well as briefly summarize other applications for environmental and food analyses as some of their used ICD reagents were further applied for analyzing biological specimens or have the potential for that.

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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

Cited by 15 publications

References 29 publications

Fluorimetric determination of the enantiomers of vigabatrin, an antiepileptic drug, by reversed‐phase HPLC with a novel diastereomer derivatization reagent

Fluorimetric determination of the enantiomers of vigabatrin, an antiepileptic drug, by reversed‐phase HPLC with a novel diastereomer derivatization reagent

Simultaneous determination of five essential amino acids in plasma of Hyperlipidemic subjects by UPLC-MS/MS

Current trends in isotope‐coded derivatization liquid chromatographic‐mass spectrometric analyses with special emphasis on their biomedical application

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