Chiral separations for d -amino acid analysis in biological samples

Szökő, Éva; Vincze, István; Tábi, Tamás

doi:10.1016/j.jpba.2016.06.054

Cited by 50 publications

(27 citation statements)

References 89 publications

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“…However, because of the recent development of sensitive and selective analytical methods for detecting chiral amino acids [125], diverse D-amino acids have been found in mammalian tissues. The physiological functions of these D-amino acids are being gradually clarified.…”

Section: Discussionmentioning

confidence: 99%

D-Amino Acids in the Nervous and Endocrine Systems

Kiriyama

Nochi

2016

Scientifica

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Amino acids are important components for peptides and proteins and act as signal transmitters. Only L-amino acids have been considered necessary in mammals, including humans. However, diverse D-amino acids, such as D-serine, D-aspartate, D-alanine, and D-cysteine, are found in mammals. Physiological roles of these D-amino acids not only in the nervous system but also in the endocrine system are being gradually revealed. N-Methyl-D-aspartate (NMDA) receptors are associated with learning and memory. D-Serine, D-aspartate, and D-alanine can all bind to NMDA receptors. H2S generated from D-cysteine reduces disulfide bonds in receptors and potentiates their activity. Aberrant receptor activity is related to diseases of the central nervous system (CNS), such as Alzheimer's disease, amyotrophic lateral sclerosis, and schizophrenia. Furthermore, D-amino acids are detected in parts of the endocrine system, such as the pineal gland, hypothalamus, pituitary gland, pancreas, adrenal gland, and testis. D-Aspartate is being investigated for the regulation of hormone release from various endocrine organs. Here we focused on recent findings regarding the synthesis and physiological functions of D-amino acids in the nervous and endocrine systems.

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Section: Discussionmentioning

confidence: 99%

D-Amino Acids in the Nervous and Endocrine Systems

Kiriyama

Nochi

2016

Scientifica

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“…Chiral analysis of amino acids is necessary in medical, biotechnological and pharmaceutical applications [104][105][106]. Although amino acids exist in nature mainly in the L-form, the presence of Dform of the amino acids has recently been confirmed in various higher organisms [107].…”

Section: Swcnts and Mwcnts For Chiral Separation In Biologicsmentioning

confidence: 99%

“…Thus, it is essential to obtain pure enantiomers of the building blocks for proteins and peptides for their therapeutic or diagnostic applications. Several HPLC methods have been applied with different chiral selectors for chiral separation of the primary, secondary as well as beta and gamma amino acids [106,108,109]. Baseline and partial enantioseparation of some amino acids by modified CNTs have been reported and discussed in the following sections.…”

Section: Swcnts and Mwcnts For Chiral Separation In Biologicsmentioning

confidence: 99%

Application of Carbon Nanotubes in Chiral and Achiral Separations of Pharmaceuticals, Biologics and Chemicals

Hemasa

Naumovski

Maher

et al. 2017

Preprint

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Carbon nanotubes (CNTs) possess unique mechanical, physical, electrical and absorbability properties coupled with their nanometer dimensional scale that renders them extremely valuable for applications in many fields including nanotechnology and chromatographic separation. The aim of this review is to provide an updated overview about the applications of CNTs in chiral and achiral separations of pharmaceuticals, biologics and chemicals. Chiral SWCNTs and MWCNTs have been directly applied for the enantioseparation of pharmaceuticals and biologicals by using them as stationary or pseudostationary phases in chromatographic separation techniques such as high-performance liquid chromatography (HPLC), capillary electrophoresis (CE) and gas chromatography (GC). Achiral MWCNTs have been used for achiral separations as efficient sorbent objects in solid-phase extraction techniques of biochemicals and drugs. Achiral SWCNTs have been applied in achiral separation of biological samples. Achiral SWCNTs and MWCNTs have been also successfully used to separate achiral mixtures of pharmaceuticals and chemicals. Collectively, functionalized CNTs have been indirectly applied in separation science by enhancing the enantioseparation of different chiral selectors whereas, non-functionalized CNTs have shown efficient capabilities for chiral separations by using techniques such as encapsulation or immobilization in polymer monolithic columns.

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“…Decreased D‐Ser levels in the plasma or serum have been reported in clinical studies of schizophrenia patients . Plasma concentrations of D‐serine and the ratio of D‐serine to total serine may be used as clinically translatable biomarkers in NMDA receptor‐related disease . D‐amino acid has been gradually accepted as a new target molecule due to its physiological effect.…”

Section: Introductionmentioning

confidence: 99%

Evaluation of chiral separation efficiency of a novel OTPTHE derivatization reagent: Applications to liquid‐chromatographic determination of DL‐serine in human plasma

Han

Jin

et al. 2019

Chirality

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A novel chiral derivatization reagent, the N‐[1‐oxo‐5‐(triphenylphosphonium)pentyl]‐ (R)‐1,3‐thiazolidinyl‐4‐N‐hydroxysuccinimide ester bromide salt (OTPTHE), was developed for the separation and selective detection of chiral DL‐amino acids by RP‐HPLC analysis. The OTPTHE reacted with DL‐amino acids at 60°C maintained for 30 minutes in the presence of 100 mM borate buffer (pH 9.5). The separability of the diastereomeric derivatives was evaluated in terms of the resolution value (Rs) using 13 kinds of DL‐amino acids, which were completely separated by reversed‐phase chromatography using C18 column at 254 nm. The Rs of the DL‐amino acids varied from 1.62 to 2.51. As for the application of the DL‐amino acids, the determination of DL‐Ser in the human plasma of healthy volunteers was performed based on our developed method. It was shown that linear calibrations were available with high coefficients of correlation (r2 > 0.9997). The limit of detection (S/N = 3) of the DL‐Ser enantiomers was 5.0 pmol; the relative standard deviations of the intraday and interday variations were below 4.56%; the accuracy ranged between 95.40%‐110.06% and 95.45%‐109.80%, respectively; the mean recoveries (%) of the DL‐Ser spiked in the human plasma were 99.49%‐103.74%. The amounts of DL‐Ser in the human plasma of healthy volunteers were determined.

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Chiral separations for d -amino acid analysis in biological samples

Cited by 50 publications

References 89 publications

D-Amino Acids in the Nervous and Endocrine Systems

D-Amino Acids in the Nervous and Endocrine Systems

Application of Carbon Nanotubes in Chiral and Achiral Separations of Pharmaceuticals, Biologics and Chemicals

Evaluation of chiral separation efficiency of a novel OTPTHE derivatization reagent: Applications to liquid‐chromatographic determination of DL‐serine in human plasma

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