Chiral mass spectrometry: An overview

Han, D; Yao, Zhongping

doi:10.1016/j.trac.2019.115763

Cited by 35 publications

(17 citation statements)

References 48 publications

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“…It was realized later that if a chiral environment could be introduced to enantiomers in the gas phase, chiral differentiation could be fulfilled by MS-relative methods. Since the electrospray ionization (ESI) method can be used to generate unstable noncovalent complexes readily, it has become the best partner of the MS-based chiral analysis method and greatly promoted the development of the research field since its invention [5][6][7][8][9][10]. In addition, it makes the MS-based chiral analysis a very attractive method compared with others due to its excellent performance in terms of rapidity, sensitivity, and specificity [9,10].…”

Section: Introductionmentioning

confidence: 99%

Application of Infrared Multiple Photon Dissociation (IRMPD) Spectroscopy in Chiral Analysis

Shi

Ren

et al. 2020

Molecules

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In recent years, methods based on photodissociation in the gas phase have become powerful means in the field of chiral analysis. Among them, infrared multiple photon dissociation (IRMPD) spectroscopy is a very attractive one, since it can provide valuable spectral and structural information of chiral complexes in addition to chiral discrimination. Experimentally, the method can be fulfilled by the isolation of target diastereomeric ions in an ion trap followed by the irradiation of a tunable IR laser. Chiral analysis is performed by comparing the difference existing in the spectra of enantiomers. Combined with theoretical calculations, their structures can be further understood on the molecular scale. By now, lots of chiral molecules, including amino acids and peptides, have been studied with the method combined with theoretical calculations. This review summarizes the relative experimental results obtained, and discusses the limitation and prospects of the method.

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Section: Introductionmentioning

confidence: 99%

Application of Infrared Multiple Photon Dissociation (IRMPD) Spectroscopy in Chiral Analysis

Shi

Ren

et al. 2020

Molecules

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“…Previous studies have shown that the generation of complex ions depends on amino acids and transition metal ions. 10,11,43,47 We first tested 210 paired combinations of 20 amino acids. In this experiment, when we used the Ser−His combination, we were able to observe mono-and dinuclear copper complex ions clearly in the mass spectra, and these four unique ions proved to be useful for isomeric differentiation.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Mass spectrometry (MS) has become the obvious choice for direct isomer identification due to its superiority in speed, sensitivity, and specificity. − The gas-phase-based methods for structural analysis can dissociate analytes into characteristic fragments indicating the linkage positions and stereochemistry . Many dissociation techniques have been used for carbohydrate studies, such as collision-induced dissociation (CID), − infrared multiphoton dissociation (IRMPD), ultraviolet photodissociation (UVPD), electron-based ion activation method (ExD), , high-energy CID (HCD), as well as combinatorial strategies like radical-directed dissociation (RDD, combines UVPD and CID), ETciD, and EThcD .…”

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confidence: 99%

Distinguishment of Glycan Isomers by Trapped Ion Mobility Spectrometry

Gao

Chen

et al. 2021

Anal. Chem.

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The in-depth study of glycan has drawn large research interests since it is one of the main biopolymers on the earth with a variety of biological functions. However, the distinguishment of glycans is still difficult due to the similarity of the monosaccharide building block, the anomer, and the linkage of glycosidic bonds. In this study, four novel and representative copper-bound diastereoisomeric complex ions were simultaneously detected in a single measurement by trapped ion mobility mass spectrometry, including mononuclear copper-bound dimeric ions [(Cu2+)(A)(l-Ser)-H]+ and [(Cu2+)(A)(l-His)-H]+, the mononuclear copper-bound trimeric ion [(Cu2+)(A)(l-Ser)(l-His)-H]+, and the binuclear copper-bound tetrameric ion [(Cu2+)2(A)(l-Ser)2(l-His)-3H]+ (where A denotes an oligosaccharide, and l-Ser and l-His denote l-serine and l-histidine, respectively). By combining the collision cross sections of complex ions, 23 oligosaccharide isomers were successfully distinguished including two pairs of sialylated glycan linkage isomers. In addition, due to the unique dissociation pathways of the trimeric ion, both the relative and absolute quantification of the individual isomer in the mixture could be determined using a mass spectrometry-based kinetic method. Finally, the method established above was successfully applied to the identification and quantification of glycan isomers in dairy beverages and juice. The method in the present study was sensitive to the fine difference of glycan isomers and might have wide applicability in glycoscience.

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“…Different IMS technologies, including linear 18−21 or nonlinear 22 methods, have been used for chiral analysis. 23 In 2006, Dwivedi et al 24 demonstrated the separation of enantiomers by creating a chiral environment in the IMS drift tube. Some chiral pharmaceuticals, amino acids, and carbohydrates were resolved by doping the drift gas with 2-butanol in drift tube IMS.…”

Section: ■ Introductionmentioning

confidence: 99%

“…As a postionization separation method in the gas phase, IMS provides the separation of ions based on their average collision cross section (CCS), which mainly depends on their size, shape, and charge state. Different IMS technologies, including linear − or nonlinear methods, have been used for chiral analysis . In 2006, Dwivedi et al demonstrated the separation of enantiomers by creating a chiral environment in the IMS drift tube.…”

Section: Introductionmentioning

confidence: 99%

Effective Chiral Discrimination of Amino Acids through Oligosaccharide Incorporation by Trapped Ion Mobility Spectrometry

Xie

et al. 2020

Anal. Chem.

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Chiral analysis is critical to many research fields due to different biological functions of enantiomers in living systems. Although the use of ion mobility spectrometry (IMS) has become an alternative technology in the area of chiral measurements, there is still a lack of a general chiral selector for IMS-based chiral recognition, especially for small chiral molecules. Here, a new method using oligosaccharides as the chiral selector has been developed to discriminate chiral amino acids (AAs) by trapped ion mobility spectrometry-mass spectrometry (TIMS-MS). We analyzed 21 chiral amino acids, including small molecules (e.g., alanine and cysteine). Our data showed that the use of nonreducing tetrasaccharides was effective for the separation of chiral AAs, which differentiated 21 chiral AAs without using metal ions. By further incorporating a copper ion, the separation resolution could be improved to 1.64 on average, which accounts for an additional 52% improvement on top of the already achieved separation in metal-free analysis. These results indicate that the use of tetrasaccharides is an effective strategy for the separation of AA enantiomers by TIMS. The method developed in this study may open up a new strategy for effective IMS-based chiral analysis.

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Chiral mass spectrometry: An overview

Cited by 35 publications

References 48 publications

Application of Infrared Multiple Photon Dissociation (IRMPD) Spectroscopy in Chiral Analysis

Application of Infrared Multiple Photon Dissociation (IRMPD) Spectroscopy in Chiral Analysis

Distinguishment of Glycan Isomers by Trapped Ion Mobility Spectrometry

Effective Chiral Discrimination of Amino Acids through Oligosaccharide Incorporation by Trapped Ion Mobility Spectrometry

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