dc.contributor.author
Sepman, Helen
dc.contributor.author
Tshepelevitsh, Sofja
dc.contributor.author
Hupatz, Henrik
dc.contributor.author
Kruve, Anneli
dc.date.accessioned
2022-09-19T07:46:40Z
dc.date.available
2022-09-19T07:46:40Z
dc.identifier.uri
https://refubium.fu-berlin.de/handle/fub188/36355
dc.identifier.uri
http://dx.doi.org/10.17169/refubium-36071
dc.description.abstract
The structural annotation of isomeric metabolites remains a key challenge in untargeted electrospray ionization/high-resolution mass spectrometry (ESI/HRMS) metabolomic analysis. Many metabolites are polyfunctional compounds that may form protomers in electrospray ionization sources and therefore yield multiple peaks in ion mobility spectra. Protomer formation is strongly structure-specific. Here, we explore the possibility of using protomer formation for structural elucidation in metabolomics on the example of caffeine, its eight metabolites, and structurally related compounds. It is observed that two-thirds of the studied compounds formed high- and low-mobility species in high-resolution ion mobility. Structures in which proton hopping was hindered by a methyl group at the purine ring nitrogen (position 3) yielded structure-indicative fragments with collision-induced dissociation (CID) for high- and low-mobility ions. For compounds where such a methyl group was not present, a gas-phase equilibrium could be observed for tautomeric species with two-dimensional ion mobility. We show that the protomer formation and the gas-phase properties of the protomers can be related to the structure of caffeine metabolites and facilitate the identification of the structural isomers.
en
dc.format.extent
9 Seiten
dc.rights.uri
https://creativecommons.org/licenses/by/4.0/
dc.subject
Molecular structure
en
dc.subject.ddc
500 Naturwissenschaften und Mathematik::540 Chemie::540 Chemie und zugeordnete Wissenschaften
dc.title
Protomer Formation Can Aid the Structural Identification of Caffeine Metabolites
dc.type
Wissenschaftlicher Artikel
dcterms.bibliographicCitation.doi
10.1021/acs.analchem.2c00257
dcterms.bibliographicCitation.journaltitle
Analytical Chemistry
dcterms.bibliographicCitation.number
30
dcterms.bibliographicCitation.pagestart
10601
dcterms.bibliographicCitation.pageend
10609
dcterms.bibliographicCitation.volume
94
dcterms.bibliographicCitation.url
https://doi.org/10.1021/acs.analchem.2c00257
refubium.affiliation
Biologie, Chemie, Pharmazie
refubium.affiliation.other
Institut für Chemie und Biochemie
refubium.resourceType.isindependentpub
no
dcterms.accessRights.openaire
open access
refubium.resourceType.provider
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