Simultaneous determination of d-aspartic acid and d-glutamic acid in rat tissues and physiological fluids using a multi-loop two-dimensional HPLC procedure

Han, Hai; Miyoshi, Y.; Ueno, Kyoko; Okamura, Chieko; Tojo, Yosuke; Mita, Masashi; Lindner, Wolfgang; Zaitsu, Kiyoshi; Hamase, Kenji

doi:10.1016/j.jchromb.2011.01.023

Cited by 67 publications

(56 citation statements)

References 39 publications

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“…The five target D-amino acids were selected because these D-amino acids are frequently observed in higher animals (as their free forms) [2][3][4][5]. In the first dimension, the five target NBD-amino acids were separated using a capillary monolithic ODS column, and the elution conditions were optimized.…”

Section: Establishment Of An Enantioselective Two-dimensional Hplc-msmentioning

confidence: 99%

“…All proteinogenic amino acids, except glycine, have optical isomers (enantiomers), namely the D-and L-forms, and L-amino acids are predominant in the higher animals. However, from the 1980s, several D-amino acids have been reported to be present as their free forms in mammalian tissues including human beings, and these D-amino acids are expected to be novel physiologically active substances and biomarkers [1][2][3][4][5]. In the proteins and peptides, D-amino acid residues, especially D-Asp, have also been reported in various disease/aged proteins including Alzheimer's disease and cataract [6][7][8][9][10][11][12].…”

Section: Introductionmentioning

confidence: 99%

“…In the present study, an analytical method has been established for the determination of D-Ala, D-Asp, D-Glu, D-Pro and D-Ser (these 5 D-amino acids are frequently observed in vertebrates [2][3][4][5]) residues in protein samples. For the analysis, a two-dimensional HPLC-MS/MS system was adopted after the DCl/D 2 O hydrolysis.…”

Section: Introductionmentioning

confidence: 99%

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Establishment of a Two-Dimensional HPLC-MS/MS Method Combined with DCl/D<sub>2</sub>O Hydrolysis for the Determination of Trace Amounts of D-Amino Acid Residues in Proteins

Ishigo

Negishi²,

Miyoshi

et al. 2015

Chromatography

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A two-dimensional (2D) HPLC-MS/MS method has been established for the determination of trace amounts of D-amino acid residues in proteins. D-Amino acid residues are now increasingly recognized as biomarkers of diseases and key moieties for the regulation of protein structures/functions, therefore, a sensitive analytical method is highly required. However, non-negligible amounts of D-amino acids are produced by chemical racemization during the hydrolysis of proteins, and a sensitive determination of D-amino acid residues is normally difficult. In the present study, DCl/D 2 O hydrolysis is adopted and the produced deuterated D-amino acids are distinguished from naturally-occurring D-amino acids in the proteins using the 2D-HPLC-MS/MS system. D-Ala, D-Asp, D-Glu, D-Pro and D-Ser (frequently observed D-amino acids in higher animals) were selected as the targets, and the sensitive determination (around 1% or less of the L-forms) could be carried out. As an application, the D-amino acid residues in ovalbumin (OVA) were determined, and the presence of a significant amount of D-Ser (1.8% of L-Ser) was demonstrated.

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Section: Establishment Of An Enantioselective Two-dimensional Hplc-msmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Establishment of a Two-Dimensional HPLC-MS/MS Method Combined with DCl/D<sub>2</sub>O Hydrolysis for the Determination of Trace Amounts of D-Amino Acid Residues in Proteins

Ishigo

Negishi²,

Miyoshi

et al. 2015

Chromatography

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“…For example, D-Ser is synthesized by serine racemase in the mammalian brain [7][8][9], and modulates neurotransmission [10][11][12]. High amounts of D-Asp are observed in the endocrine/neuro-endocrine tissues [13][14][15], and this D-amino acid regulates hormonal synthesis/secretion [16].…”

Section: Introductionmentioning

confidence: 99%

Sleep-Awake Profile Related Circadian D-Alanine Rhythm in Human Serum and Urine

et al. 2017

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The circadian profiles of D-alanine (Ala) amounts in human serum and urine have been clarified using a two-dimensional HPLC system combining a microbore reversed-phase C18 column and a Pirkle-type enantioselective column. The two-dimensional HPLC system enables the determination of trace amounts of D-Ala in the clinical samples without severe interference from intrinsic substances in the human physiological fluids. In the volunteers having normal sleep-awake patterns, the amounts of D-Ala in the serum were high in the late evening and low in the morning. On the other hand, in the volunteers having the reversed sleep-awake patterns, the amounts of D-Ala in the serum were high in the morning and low in the nighttime. The similar circadian changes of D-Ala amounts were observed in the urine. These 24-h profiles of D-Ala are almost the same as those observed in rats and mice, suggesting that D-Ala has fundamental physiological functions related to rest-active conditions in mammals, and could also be useful as the biomarker for sleep-awake profiles.

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“…D-Aspartic acid (D-Asp), the enantiomer of proteinogenic L-aspartic acid (L-Asp), is an endogenous D-amino acid widely observed in mammalian brain and peripheral tissues [1][2][3][4][5][6][7][8]. As the enzyme synthesizing D-Asp, mammalian aspartate racemase (DR), which converts L-Asp to D-Asp, was found in 2010 in the brain and neuroendocrine tissues of mice [9], and this D-amino acid is becoming noticed as an endogenous physiologically active substance.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective micro‐2D‐HPLC determination of aspartic acid in the pineal glands of rodents with various melatonin contents

Han

Miyoshi

Oyama

et al. 2011

J of Separation Science

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Enantioselective determination of aspartic acid (Asp) in the pineal gland of rodents with various melatonin contents was performed using a highly sensitive and selective two-dimensional HPLC system. After derivatization of the amino group with 4-fluoro-7-nitro-2,1,3-benzoxadiazole (NBD-F), NBD-Asp was separated using a capillary monolithic ODS column in the first dimension. The fraction of NBD-Asp was automatically collected and transferred to the second dimension, and the D- and L-Asp were separated and determined using a narrowbore enantioselective column. Large amounts of D-Asp were observed in the pineal gland of the rats and specific strains of mice (C3H and CBA) possessing a high concentration of melatonin in their pineal gland. On the other hand, the amounts of D-Asp were small in the pineal gland of mice possessing a trace or no melatonin in their pineal gland (ddY, ICR, C57BL and BALB/c). In other tissues and physiological fluids, no significant strain-dependent changes of the D-Asp amounts were observed. These results indicate that large amounts of D-Asp are present only in the pineal gland containing large amounts of melatonin, and special care should be taken when selecting mouse strains for the investigation of D-Asp.

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Simultaneous determination of d-aspartic acid and d-glutamic acid in rat tissues and physiological fluids using a multi-loop two-dimensional HPLC procedure

Cited by 67 publications

References 39 publications

Establishment of a Two-Dimensional HPLC-MS/MS Method Combined with DCl/D<sub>2</sub>O Hydrolysis for the Determination of Trace Amounts of D-Amino Acid Residues in Proteins

Establishment of a Two-Dimensional HPLC-MS/MS Method Combined with DCl/D<sub>2</sub>O Hydrolysis for the Determination of Trace Amounts of D-Amino Acid Residues in Proteins

Sleep-Awake Profile Related Circadian D-Alanine Rhythm in Human Serum and Urine

Enantioselective micro‐2D‐HPLC determination of aspartic acid in the pineal glands of rodents with various melatonin contents

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