Investigating carbohydrate isomers by IMS-CID-IMS-MS: precursor and fragment ion cross-sections

Gaye, Maissa M.; Kurulugama, Ruwan T.; Clemmer, David E.

doi:10.1039/c5an00840a

Cited by 66 publications

(70 citation statements)

References 41 publications

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“…2. Their drift-time distributions overlap, making them virtually indistinguishable by ion mobility, as reported previously for glycans of this size [13]. We then measured their vibrational spectra, using hydrogen as the tag molecule and keeping the trap temperature at 13 K. As one can see in Fig.…”

Section: Resultsmentioning

confidence: 76%

“…The mobility of an ion through a gas is related to its orientationally averaged collisional cross section (CCS), which reflects its overall shape. While in some cases the structures of different isomeric glycan species can be distinguished by their CCS, in many others cases the structural differences are too subtle to detect in this way [13]. To solve this fundamental problem, one needs to add an orthogonal dimension to these measurements that will allow the discrimination between any pair of isomeric glycans.…”

Section: Introductionmentioning

confidence: 99%

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Cryogenic Vibrational Spectroscopy Provides Unique Fingerprints for Glycan Identification

Masellis

Khanal

Kamrath

et al. 2017

J. Am. Soc. Mass Spectrom.

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The structural characterization of glycans by mass spectrometry is particularly challenging. This is due to the high degree of isomerism in which glycans of the same mass can differ in their stereochemistry, attachment points, and degree of branching. Here we show that the addition of cryogenic vibrational spectroscopy to mass and mobility measurements allows one to uniquely identify and characterize these complex biopolymers. We investigate six disaccharide isomers that differ in their stereochemistry, attachment point of the glycosidic bond, and monosaccharide content, and demonstrate that we can identify each one unambiguously. Even disaccharides that differ by a single stereogenic center or in the monosaccharide sequence order show distinct vibrational fingerprints that would clearly allow their identification in a mixture, which is not possible by ion mobility/mass spectrometry alone. Moreover, this technique can be applied to larger glycans, which we demonstrate by distinguishing isomeric branched and linear pentasaccharides. The creation of a database containing mass, collisional cross section and vibrational fingerprint measurements for glycan standards should allow unambiguous identification and characterization of these biopolymers in mixtures, providing an enabling technology for all fields of glycoscience.

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Section: Resultsmentioning

confidence: 76%

Section: Introductionmentioning

confidence: 99%

Cryogenic Vibrational Spectroscopy Provides Unique Fingerprints for Glycan Identification

Masellis

Khanal

Kamrath

et al. 2017

J. Am. Soc. Mass Spectrom.

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show abstract

“…Ion mobility spectrometry is a powerful tool for the gas-phase separation of carbohydrates, either as a standalone technique 115,116 or via coupling with other analytical techniques 117 . A recent study has shown that non-derivatized glycans can be separated through a reversed-phase column on a liquid chromatography-ion mobility-mass spectrometry (LC-IM-MS) instrument 118 .…”

Section: Ease Of Coupling To Other Techniquesmentioning

confidence: 99%

Recent liquid chromatographic approaches and developments for the separation and purification of carbohydrates

2017

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“…Although its hyphenation with MS in commercial instrumentation is a more recent development, it has already created new possibilities for the characterization of some classes of small molecules and metabolites [9][10][11]. Specific examples are the separation of isomeric disaccharides [12][13][14] and metal(-ligand) complexes [15][16][17] or the characterization of carbohydrate, glycan and lipid structures [18][19][20][21][22][23]. Particular interest recently focused on the phenomenon of alternative charge sites in small molecules that are observed in the gas phase, i.e.…”

Section: Introductionmentioning

confidence: 99%

Analyzing complex mixtures of drug-like molecules: Ion mobility as an adjunct to existing liquid chromatography-(tandem) mass spectrometry methods

Boschmans

Lemière

Sobott

2017

Journal of Chromatography A

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Please cite this article as: Jasper Boschmans, Filip Lemière, Frank Sobott, Analyzing complex mixtures of drug-like molecules: ion mobility as an adjunct to existing liquid chromatography-(tandem) mass spectrometry methods, Journal of Chromatography A http://dx.doi.org/10. 1016/j.chroma.2017.02.015 This is a PDF Þle of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its Þnal form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. AbstractThe use of traveling wave ion mobility mass spectrometry (TWIMS) is evaluated in conjunction with, and as a possible alternative to, conventional LC-MS(/MS) methods for the separation and characterization of drug-like compounds and metabolites. As a model system we use an in vitro incubation mixture of the chemotherapeutic agent melphalan, which results in more than ten closely related hydrolysis products and chain-like oligomers. Ion mobility as a filtering tool results in the separation of ions of interest from interfering ions, based on charge state and shape/size. Different classes of chemical compounds often display different mobilities even if they show the same LC behavior -thereby providing an orthogonal separation dimension. Small molecules with identical or similar m/z that only differ in shape/size (e.g. isomers and isobars, monomers/dimers) can also be distinguished using ion mobility. Similar to retention times and mass-to-charge ratios, drift times are analyte-dependent and can be used as an additional identifier. We find that the compound melphalan shows two different drift times due to the formation of gas-phase charge isomers (protomers). The occurrence of protomers has important implications for ion mobility characterization of such analytes, and also for the interpretation of their fragmentation behavior (CID) in the gas phase.

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Investigating carbohydrate isomers by IMS-CID-IMS-MS: precursor and fragment ion cross-sections

Cited by 66 publications

References 41 publications

Cryogenic Vibrational Spectroscopy Provides Unique Fingerprints for Glycan Identification

Cryogenic Vibrational Spectroscopy Provides Unique Fingerprints for Glycan Identification

Recent liquid chromatographic approaches and developments for the separation and purification of carbohydrates

Analyzing complex mixtures of drug-like molecules: Ion mobility as an adjunct to existing liquid chromatography-(tandem) mass spectrometry methods

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