Development of a liquid chromatography-tandem mass spectrometry method for quantitative analysis of trace d-amino acids

Nakano, Yukiko; Konya, Yutaka; Taniguchi, Moyu; Fukusaki, Eiichiro

doi:10.1016/j.jbiosc.2016.07.008

Cited by 52 publications

(28 citation statements)

References 36 publications

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“…The method was found to be very efficient for cationization of various LMW compounds . Amino acids are commonly detected with the use of liquid chromatography‐mass spectrometry (LC‐MS) approach . However, there are only few publications presenting laser desorption/ionization approaches …”

Section: Introductionmentioning

confidence: 99%

“…11 Amino acids are commonly detected with the use of liquid chromatography-mass spectrometry (LC-MS) approach. [12][13][14][15] However, there are only few publications presenting laser desorption/ionization approaches. [16][17][18] In this work, we present results aimed at detection and quantification of amino acids along with discussion of results and comparison with different mass spectrometry methods.…”

Section: Introductionmentioning

confidence: 99%

“…12 ng/mL. A LC-MS approach applied by Moldoveanu and other groups allowed detection at similar, subnanogram per milliliter level [12][13][14][15].…”

mentioning

confidence: 99%

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Silver‐109‐based laser desorption/ionization mass spectrometry method for detection and quantification of amino acids

2018

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A new methodology applicable for both high-resolution laser desorption/ionization mass spectrometry and mass spectrometry imaging of amino acids is presented. The matrix-assisted laser desorption ionization-type target containing monoisotopic cationic Ag nanoparticles ( AgNPs) was used for rapid mass spectrometry measurements of 11 amino acids of different chemical properties. Amino acids were directly tested in 100,000-fold concentration change conditions ranging from 100 μg/mL to 1 ng/mL which equates to 50 ng to 500 fg of amino acid per measurement spot. Limit of detection values obtained suggest that presented method/target system is among the fastest and most sensitive ones in laser mass spectrometry. Mass spectrometry imaging of spots of human blood plasma spiked with amino acids showed their surface distribution allowing optimization of quantitative measurements.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Silver‐109‐based laser desorption/ionization mass spectrometry method for detection and quantification of amino acids

2018

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“…As the MS compatible diastereomer forming reagents, 4-(3-isothiocyanatopyrrolidin-1-yl)-7-(N, N-dimethylaminosulfonyl)-2,1,3-benzoxadiazole [30], N-(4-nitrophenoxycarbonyl)-L-phenylalanine-2-methoxyethyl ester [31] and some others are used. Chiral LC-MS/MS methods using enantioselective columns as the separation media were also reported [32,33]. These HPLC methods are widely used for the determination of D-amino acids in tissues and physiological fluids, for example, D-Ser in the brain and D-Asp in the endocrine tissues.…”

Section: D-alamentioning

confidence: 99%

Development of a Highly-Sensitive Two-Dimensional HPLC System with Narrowbore Reversed-Phase and Microbore Enantioselective Columns and Application to the Chiral Amino Acid Analysis of the Mammalian Brain

et al. 2018

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A highly-sensitive two-dimensional high-performance liquid chromatographic (2D-HPLC) system with narrowbore reversed-phase and microbore enantioselective columns has been developed for the determination of alanine (Ala) and serine (Ser) enantiomers. The amounts of D-amino acids in biological samples are extremely low in most cases and improvement in the sensitivity is still required. For a highly-sensitive analysis, a narrowbore reversed-phase column, KSAARP (1.5 mm x 500 mm, having a wider ID than the microbore column) was used in the first dimension, and a microbore enantioselective column, KSAACSP-001S (1.0 mm x 250 mm, having a narrower ID than the frequently reported enantioselective columns) was used in the second dimension. The amino acids were derivatized with 4-fluoro-7-nitro-2,1,3-benzoxadiazole and detected by the fluorescence detectors. The 2D-HPLC system was validated using a mouse cerebrum in addition to the standard amino acids, and satisfactory calibration lines and precision results were obtained. In the mouse cerebrum, a large amount of D-Ser and a small amount of D-Ala were clearly observed. These results indicated that the present method is applicable to the determination of the trace amounts of D-amino acids in tissue samples.

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“…It is clear that MS possesses advantages such as rapid analysis, high sensitivity, and reduced sample consumption; it also does not necessitate isotope labeling or other derivatization treatment to analytes. Currently, there are 4 major types of MS techniques used in chiral recognition: (1) the host‐guest method, (2) ion/molecule (equilibrium) reactions, (3) collision‐induced dissociation of diastereomeric complex (which includes the kinetic method [KM], the fixed ligand KM, and the chiral recognition ratio method) and (4) ion mobility MS . The most commonly used type is KM because the experimental data interpretation is much easier because only the relative abundances of 2 fragment ions are needed and isomer separation is not necessary.…”

Section: Introductionmentioning

confidence: 99%

Chiral detection of entecavir stereoisomeric impurities through coordination with R‐besivance and Zn^II using mass spectrometry

Wang

Chen

et al. 2018

J Mass Spectrom

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In this study, a mass spectrometry (MS)-based kinetic method (KM) is shown to be successful at analyzing a multichiral center drug stereoisomer, entecavir (ETV), both qualitatively and quantitatively. On the basis of the KM, the bivalent complex ion [M (A)(ref*) ] (M = divalent metal ion, A = analyte, and ref* = chiral reference) was set as precursor ion in MS/MS. The experiment results suggest strong chiral selectivity between ETV and its isomers when using Zn coordinated with the chiral reference R-besivance (R-B). The logarithm of the fragment ion abundance ratio and the enantiomeric percentage (%) exhibits a strong linear relation because of the competitive loss of the reference and analyte. The product ion pair [Zn (R-B)A-H] (m/z 733) and [Zn (R-B) -H] (m/z 849), together with [R-B + H] (m/z 394) and [A + H] (m/z 278), can realize the identification of ETV and all of its chiral isomers. Theoretical calculation were also performed using the B3LYP functional with the 6-31G* and LanL2DZ basis set to clarify the mechanism of structural difference of these bivalent complex ions. The results reveal that MS-KM can be used to detect optical impurities without a chiral chromatographic column and fussy sample pretreatment. The established method has been used to determine stereoisomeric impurities of less than 0.1% in ETV crude drug, a demonstration of its simple and effective nature for rapid detection of stereoisomeric impurities.

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Development of a liquid chromatography-tandem mass spectrometry method for quantitative analysis of trace d-amino acids

Cited by 52 publications

References 36 publications

Silver‐109‐based laser desorption/ionization mass spectrometry method for detection and quantification of amino acids

Silver‐109‐based laser desorption/ionization mass spectrometry method for detection and quantification of amino acids

Development of a Highly-Sensitive Two-Dimensional HPLC System with Narrowbore Reversed-Phase and Microbore Enantioselective Columns and Application to the Chiral Amino Acid Analysis of the Mammalian Brain

Chiral detection of entecavir stereoisomeric impurities through coordination with R‐besivance and Zn^II using mass spectrometry

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Development of a liquid chromatography-tandem mass spectrometry method for quantitative analysis of trace d-amino acids

Cited by 52 publications

References 36 publications

Silver‐109‐based laser desorption/ionization mass spectrometry method for detection and quantification of amino acids

Silver‐109‐based laser desorption/ionization mass spectrometry method for detection and quantification of amino acids

Development of a Highly-Sensitive Two-Dimensional HPLC System with Narrowbore Reversed-Phase and Microbore Enantioselective Columns and Application to the Chiral Amino Acid Analysis of the Mammalian Brain

Chiral detection of entecavir stereoisomeric impurities through coordination with R‐besivance and ZnII using mass spectrometry

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Chiral detection of entecavir stereoisomeric impurities through coordination with R‐besivance and Zn^II using mass spectrometry