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    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. © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

    Citation

    Carla Kirschbaum, Essa M Saied, Kim Greis, Eike Mucha, Sandy Gewinner, Wieland Schöllkopf, Gerard Meijer, Gert von Helden, Berwyck L J Poad, Stephen J Blanksby, Christoph Arenz, Kevin Pagel. Resolving Sphingolipid Isomers Using Cryogenic Infrared Spectroscopy. Angewandte Chemie (International ed. in English). 2020 Aug 03;59(32):13638-13642

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    PMID: 32291895

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