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  Resolving Sphingolipid Isomers Using Cryogenic Infrared Spectroscopy

Kirschbaum, C., Saied, E. M., Greis, K., Mucha, E., Gewinner, S., Schöllkopf, W., et al. (2020). Resolving Sphingolipid Isomers Using Cryogenic Infrared Spectroscopy. Angewandte Chemie International Edition, 59(32), 13638-13642. doi:10.1002/anie.202002459.

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 Creators:
Kirschbaum, Carla1, 2, Author           
Saied, Essa M.3, 4, Author
Greis, Kim1, 2, Author           
Mucha, Eike2, Author           
Gewinner, Sandy2, Author           
Schöllkopf, Wieland2, Author           
Meijer, Gerard2, Author           
Helden, Gert von2, Author           
Poad, Berwyck L. J.5, Author
Blanksby, Stephen J.5, Author
Arenz, Christoph3, Author
Pagel, Kevin1, 2, Author           
Affiliations:
1Institut für Chemie und Biochemie, Freie Universität, Arnimallee 22, 14195 Berlin (Germany), ou_persistent22              
2Molecular Physics, Fritz Haber Institute, Max Planck Society, ou_634545              
3Institut für Chemie, Humboldt-Universität zu Berlin, Brook-Taylor-Straße 2, 12489 Berlin (Germany), ou_persistent22              
4Chemistry Department, Faculty of Science, Suez Canal University, Ismailia (Egypt), ou_persistent22              
5Central Analytical Research Facility, Institute for Future Environ- ments, Queensland University of Technology, Brisbane, QLD 4000 (Australia), ou_persistent22              

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Free keywords: deoxysphingolipids double-bond isomers IR spectroscopy isomers mass spectrometry
 Abstract: 1‐Deoxysphingolipids are a recently described class of sphingolipids that have been shown to be associated with several disease states including diabetic and hereditary neuropathy. The identification and characterization of 1‐deoxysphingolipids and their metabolites is therefore highly important. However, exact structure determination requires a combination of sophisticated analytical techniques due to the presence of various isomers, such as ketone/alkenol isomers, carbon–carbon double‐bond (C=C) isomers and hydroxylation regioisomers. Here we demonstrate that cryogenic gas‐phase infrared (IR) spectroscopy of ionized 1‐deoxysphingolipids enables the identification and differentiation of isomers by their unique spectroscopic fingerprints. In particular, C=C bond positions and stereochemical configurations can be distinguished by specific interactions between the charged amine and the double bond. The results demonstrate the power of gas‐phase IR spectroscopy to overcome the challenge of isomer resolution in conventional mass spectrometry and pave the way for deeper analysis of the lipidome.

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Language(s): eng - English
 Dates: 2020-02-172020-04-152020-05-182020-08-03
 Publication Status: Published in print
 Pages: 5
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.202002459
 Degree: -

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Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem. Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: 5 Volume / Issue: 59 (32) Sequence Number: - Start / End Page: 13638 - 13642 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851