Simultaneous analysis of monosaccharides using ultra high performance liquid chromatography-high resolution mass spectrometry without derivatization for validation of certified reference materials

Han, Boyoung; Park, Jin Woo; Kang, Minjeong; Kim, Byung-Joo; Jeong, Ji‐Seon; Kwon, Oh‐Seung; Son, Junghyun

doi:10.1016/j.jchromb.2020.122370

Cited by 12 publications

(12 citation statements)

References 47 publications

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“…The major strengths of our method are as follows: first, derivatization markedly enhanced detection sensitivity and chromatographic separation compared with direct analysis. Our derivatization method offered LOQs of monosaccharides at 0.25 to 3.00 fmol, much lower than the pmol level for underivatized methods. , A C18 column rather than a HILIC column was employed, shortening analytical time to 16 min from more than 30 min and greatly improving peak shapes. , Second, another remarkable feature of this work is that the synthesized deuterium-labeled isotope reagent could achieve paired derivatization. The main advantage of the method is the production of one-to-one ISs for various monosaccharides in order to overcome complex matrix effects in biological samples and calibrate injection-to-injection inconsistency often encountered in MS analysis.…”

Section: Resultsmentioning

confidence: 96%

“…A major limitation of GC analysis is the formation of interfering isomers during the derivatization process. , Capillary electrophoresis shows high resolution and analytical efficiency, but it is insufficient for the detection of minute levels of monosaccharides. , High-performance anion-exchange chromatography with pulsed amperometric detection, when employed for monosaccharide analyses, suffers from relatively weak separation efficiency and low sensitivity . Hydrophilic interaction chromatography provides direct detection of monosaccharides without precolumn derivatization. , Peak drifting and tailing, however, are frequently observed. Ion mobility spectrometry (IMS) techniques, including cyclic IMS and structures for lossless ion manipulation, have been applied for analyses of monosaccharides or glycans when coupled to MS − or cryogenic infrared spectroscopy .…”

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confidence: 99%

“…11 Hydrophilic interaction chromatography provides direct detection of monosaccharides without precolumn derivatization. 12,13 Peak drifting and tailing, however, are frequently observed. Ion mobility spectrometry (IMS) techniques, including cyclic IMS and structures for lossless ion manipulation, have been applied for analyses of monosaccharides or glycans when coupled to MS 14−17 or cryogenic infrared spectroscopy.…”

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confidence: 99%

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Paired Derivatization Approach with H/D-Labeled Hydroxylamine Reagents for Sensitive and Accurate Analysis of Monosaccharides by Liquid Chromatography Tandem Mass Spectrometry

Wang

et al. 2022

Anal. Chem.

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Monosaccharides play important roles in biological processes. Sensitive and accurate analyses of monosaccharides remain challenging because of their high hydrophilicities and poor ionization efficiencies. Here, we developed a paired derivatization approach with H/D-labeled hydroxylamines for simultaneous quantification of 12 monosaccharides by liquid chromatography tandem mass spectrometry (LC–MS/MS). O-(4-Methoxybenzyl)hydroxylamine hydrochloride (4-MOBHA·HCl) showed higher derivatization efficiency for monosaccharides compared to six other hydroxylamine analogues. The derivatization of monosaccharides was readily achieved in an aqueous solution. Furthermore, the deuterium-labeled isotope reagent, d 3-4-MOBHA·HCl, was newly synthesized to stably label monosaccharides to improve its accuracy and precision in complex matrix analysis. As a result, 12 monosaccharides were rapidly detected by LC–MS/MS within 16 min with significant improvements in chromatographic separation and retention time. The detection sensitivity increased by 83 to 1600-fold with limits of quantitation ranging from 0.25 to 3.00 fmol. With the paired derivatization strategy, the monosaccharides could be accurately quantified with good linearity (R 2 > 0.99) and satisfactory accuracy (recoveries: 85–110%). Using this method, we achieved sensitive and accurate quantification of the monosaccharide composition of herbal polysaccharides and the change in monosaccharide levels in human cell lines under physiopathological conditions. More importantly, the developed method was able to differentiate between the levels of the monosaccharides in fecal samples of human ulcerative colitis (UC) patients and UC mice compared to their respective controls. The differential monosaccharides determined in human feces provided a good diagnostic performance in distinguishing the UC patients from healthy individuals, showing potential for clinical application.

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confidence: 96%

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Paired Derivatization Approach with H/D-Labeled Hydroxylamine Reagents for Sensitive and Accurate Analysis of Monosaccharides by Liquid Chromatography Tandem Mass Spectrometry

Wang

et al. 2022

Anal. Chem.

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“…Numerous studies have focused on the differentiation and identification of disaccharide isomers but rarely reported on their quantitative analysis. , The kinetic method using the measurement of a trimeric ion cluster consisting of metal ions, reference molecules, and analytes was frequently used to quantify monosaccharides or disaccharides. , However, the clusters suffer from a complex operation, poor stability, and reproducibility. Recently, quantitative analysis of glucose-containing disaccharides was achieved using N -(1-naphthyl) ethylenediamine dihydrochloride (NEDC) as a matrix using matrix-assisted laser desorption/ionization mass spectrometry (MALDI-MS) in a negative mode. , Subject to the constraints of MALDI-MS itself, the detection of underactivated disaccharides had poor reducibility and low sensitivity (typically μM) because the hydrophobic nature of sugar was not effectively improved …”

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confidence: 99%

“…26,34 The kinetic method using the measurement of a trimeric ion cluster consisting of metal ions, reference molecules, and analytes was frequently used to quantify monosaccharides or disaccharides. 35,36 However, the clusters suffer from a complex operation, poor stability, and reproducibility. Recently, quantitative analysis of glucosecontaining disaccharides was achieved using N-(1-naphthyl) ethylenediamine dihydrochloride (NEDC) as a matrix using matrix-assisted laser desorption/ionization mass spectrometry (MALDI-MS) in a negative mode.…”

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confidence: 99%

Carboxyl-Based CPMP Tag for Ultrasensitive Analysis of Disaccharides by Negative Tandem Mass Spectrometry

Chen

Zhang

et al. 2022

Anal. Chem.

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Here, we develop a sensitive method for glucose-containing disaccharide analysis by 1-(4-carboxyphenyl)-3-methyl-5-pyrazolone (CPMP) derivatization using mass spectrometry. The intense anion of [M − H] − (m/z 759) was observed for CPMP-labeled disaccharides in a negative mode. After derivatization, its sensitivity was significantly increased with the limits of detection (LODs) and limits of quantification (LOQ) ranging from 3.90 to 8.67 ng L −1 and 12.99 to 28.92 ng L −1 , respectively. During CID-MS/MS analysis, the fragment patterns of CPMP derivatized disaccharides in the negative mode were simpler and clearer than their counterparts in a positive mode, which further could be applied to distinct and relatively quantitative isomeric disaccharides with ultrahigh sensitivity and good reproducibility. The great linear relationships could be achieved under wider concentration ratios from 0.01 to 20 compared to the previous report. Eventually, the developed methodology was applicable to identify isomeric disaccharides in beers. No sucrose was discovered. All beers contain 1,4-and 1,6-linked disaccharides. Some of them also have a mixture of 1,2-and 1,3-linked disaccharides. Through the integration of statistical analysis, beers with different production processes were finally discriminated, and the relative quantification of isomaltose and maltose was realized. In general, this method is sensitive, fast, and reliable for the discrimination and relative quantification of isomeric disaccharides in complex matrices. This study provides a new idea for the structural analysis of oligosaccharides in food, plants, and animals and an important theoretical basis for the exploration of new functions of oligosaccharides.

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Development of a joint derivatization protocol for the unequivocal identification of the monosaccharide composition in four dendrobium polysaccharides and free monosaccharide by GC–MS

Yang,

Hao,

Chen

et al. 2023

Biomedical Chromatography

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The determination of monosaccharides is crucial for studying the structure of polysaccharides and the composition of free monosaccharides in living organisms. Based on previous derivatization gas chromatography–mass spectrometry (GC–MS) methods, we aimed to develop a novel analytical protocol for better quantifying monosaccharides. In this study, sugar alcohol acetylation, saccharonitrile acetylation, silylation and a combination of sugar alcohols acetylation and saccharonitrile acetylation were compared. The optimal method was verified with the monosaccharide determination of four polysaccharides and four free monosaccharides from Dendrobium. The results showed that the novel combined derivatization method was superior to the other three methods in terms of content analysis of monosaccharides. Furthermore, it possessed good linearity (all calibration curves showed relative coefficients ≥ 0.999), sensitivity, precision (relative standard deviation < 2%), and accuracy (recovery, 95.7–105%). Finally, the novel method established in this study was successfully employed in determining the monosaccharide composition of four polysaccharides and four free monosaccharide samples from Dendrobium.

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Simultaneous analysis of monosaccharides using ultra high performance liquid chromatography-high resolution mass spectrometry without derivatization for validation of certified reference materials

Cited by 12 publications

References 47 publications

Paired Derivatization Approach with H/D-Labeled Hydroxylamine Reagents for Sensitive and Accurate Analysis of Monosaccharides by Liquid Chromatography Tandem Mass Spectrometry

Paired Derivatization Approach with H/D-Labeled Hydroxylamine Reagents for Sensitive and Accurate Analysis of Monosaccharides by Liquid Chromatography Tandem Mass Spectrometry

Carboxyl-Based CPMP Tag for Ultrasensitive Analysis of Disaccharides by Negative Tandem Mass Spectrometry

Development of a joint derivatization protocol for the unequivocal identification of the monosaccharide composition in four dendrobium polysaccharides and free monosaccharide by GC–MS

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