Identification of isomeric disaccharides in mixture by the 1-phenyl-3-methyl-5-pyrazolone labeling technique in conjunction with electrospray ionization tandem mass spectrometry

Wan, Debin; Yang, Hongmei; Song, Fengrui; Liu, Zhiqiang; Liu, Shuying

doi:10.1016/j.aca.2013.03.062

Cited by 12 publications

(7 citation statements)

References 51 publications

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“…The structures of the oligosaccharides are in many cases related to their multiple important biological functions, while structural analysis of carbohydrates is still challenging because of the enormous structural diversity and microheterogeneity [16][17][18]. With the development of MS, MS-based technology has become a pivotal methodology for structural elucidation of carbohydrates [19][20][21][22][23][24][25][26][27][28]. In our recent reports [22][23][24], oligosaccharide isomers were successfully distinguished by laserenhanced in-source decay (LEISD) of matrix-assisted laser desorption/ionization (MALDI) MS or 1-phenyl-3-methyl-5-pyrazolone labeling technique in conjunction with electrospray ionization (ESI) tandem mass spectrometry.…”

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confidence: 99%

“…With the development of MS, MS-based technology has become a pivotal methodology for structural elucidation of carbohydrates [19][20][21][22][23][24][25][26][27][28]. In our recent reports [22][23][24], oligosaccharide isomers were successfully distinguished by laserenhanced in-source decay (LEISD) of matrix-assisted laser desorption/ionization (MALDI) MS or 1-phenyl-3-methyl-5-pyrazolone labeling technique in conjunction with electrospray ionization (ESI) tandem mass spectrometry. The monosaccharide structural isomers could exhibit different mobility drift times in both drift tube and traveling wave ion mobility mass spectrometry, depending on differences in their anomeric and stereochemical configurations [26].…”

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confidence: 99%

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Differentiation of Disaccharide Isomers by Temperature-Dependent In-Source Decay (TDISD) and DART-Q-TOF MS/MS

Yang

Shi

Yao

et al. 2015

J. Am. Soc. Mass Spectrom.

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Abstract. Helium direct analysis in real time (He-DART) mass spectrometry (MS) of some compounds, polysaccharides, for example, usually tends to be challenging because of the occurrence of prominent in-source decay (ISD), which was considered as an undesired side reaction, as it complicated the resulting mass spectra. Our approach is to take advantage of an efficient and practical method termed the temperature-dependent ISD (TDISD) technique combined with fragmentation of the dehydrated dimers using DART Q-TOF tandem mass spectrometry for differentiation of disaccharide isomers. In this study, cross-ring cleavages and non-ovalent complexes were detected in the spectra of the saccharides. It was observed that the gas heater temperature had a significant effect on the absence or presence of signal in DART spectra. At high gas temperature, ions in high mass region began to appear. Based on the types of crossring cleavages and noncovalent complexes, disaccharide isomers with different linkage positions can be differentiated in both positive and negative ion modes at a lower DART gas temperature. Additionally, anomeric configurations were assigned on the basis of the relative abundance ratio of m/z 198:342 obtained by the comparison of the positive ion mode tandem mass spectrum of an α isomer dimer generated at higher DART gas temperature and that of the corresponding β one. In general, this method is easy, fast, effective, and robust for identifying disaccharide isomers.

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Differentiation of Disaccharide Isomers by Temperature-Dependent In-Source Decay (TDISD) and DART-Q-TOF MS/MS

Yang

Shi

Yao

et al. 2015

J. Am. Soc. Mass Spectrom.

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“…The labeling reagent solution used for derivatization (250 mM) was prepared by dissolving 60.67 mg of PMP into 10 mL NH 3 ·H 2 O-methanol solution. PMP derivatization of ginseng carbohydrates and standard saccharides were prepared by the reaction with PMP labeling reagent at 70 °C for 120 min ( Wan et al, 2013 ; Yang et al, 2016 ). The detailed derivatization procedures are included in the Supplementary Information.…”

Section: Methodsmentioning

confidence: 99%

Distinctive carbohydrate profiles of black ginseng revealed by IM-MS combined with PMP labeling and multivariate data analysis

Shao

Xu²,

Xie³

et al. 2022

Current Research in Food Science

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“…The labeling reagent solution used for derivatization (250 mM) was prepared by dissolving 60.67 mg of PMP into 10 mL NH 3 ·H 2 O–methanol solution. PMP and PHN derivatives of monosaccharides and disaccharides were prepared according to the previously described procedures4344. The detailed derivatization procedures are included in the Supplementary Information.…”

Section: Methodsmentioning

confidence: 99%

Identification of structurally closely related monosaccharide and disaccharide isomers by PMP labeling in conjunction with IM-MS/MS

Yang

Shi²,

Zhuang

et al. 2016

Sci Rep

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It remains particularly difficult for gaining unambiguous information on anomer, linkage, and position isomers of oligosaccharides using conventional mass spectrometry (MS) methods. In our laboratory, an ion mobility (IM) shift strategy was employed to improve confidence in the identification of structurally closely related disaccharide and monosaccharide isomers using IMMS. Higher separation between structural isomers was achieved using 1-phenyl-3-methyl-5-pyrazolone (PMP) derivatization in comparison with phenylhydrazine (PHN) derivatization. Furthermore, the combination of pre-IM fragmentation of PMP derivatives provided sufficient resolution to separate the isomers not resolved in the IMMS. To chart the structural variation observed in IMMS, the collision cross sections (CCSs) for the corresponding ions were measured. We analyzed nine disaccharide and three monosaccharide isomers that differ in composition, linkages, or configuration. Our data show that coexisting carbohydrate isomers can be identified by the PMP labeling technique in conjunction with ion-mobility separation and tandem mass spectrometry. The practical application of this rapid and effective method that requires only small amounts of sample is demonstrated by the successful analysis of water-soluble ginseng extract. This demonstrated the potential of this method to measure a variety of heterogeneous sample mixtures, which may have an important impact on the field of glycomics.

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Identification of isomeric disaccharides in mixture by the 1-phenyl-3-methyl-5-pyrazolone labeling technique in conjunction with electrospray ionization tandem mass spectrometry

Cited by 12 publications

References 51 publications

Differentiation of Disaccharide Isomers by Temperature-Dependent In-Source Decay (TDISD) and DART-Q-TOF MS/MS

Differentiation of Disaccharide Isomers by Temperature-Dependent In-Source Decay (TDISD) and DART-Q-TOF MS/MS

Distinctive carbohydrate profiles of black ginseng revealed by IM-MS combined with PMP labeling and multivariate data analysis

Identification of structurally closely related monosaccharide and disaccharide isomers by PMP labeling in conjunction with IM-MS/MS

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