ACS Publications. Most Trusted. Most Cited. Most Read
Distinguishing Galactoside Isomers with Mass Spectrometry and Gas-Phase Infrared Spectroscopy
My Activity

Figure 1Loading Img
    Communication

    Distinguishing Galactoside Isomers with Mass Spectrometry and Gas-Phase Infrared Spectroscopy
    Click to copy article linkArticle link copied!

    Other Access OptionsSupporting Information (1)

    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2021, 143, 28, 10509–10513
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jacs.0c11919
    Published July 8, 2021
    Copyright © 2021 American Chemical Society

    Abstract

    Click to copy section linkSection link copied!
    Abstract Image

    Sequencing glycans is demanding due to their structural diversity. Compared to mammalian glycans, bacterial glycans pose a steeper challenge because they are constructed from a larger pool of monosaccharide building blocks, including pyranose and furanose isomers. Though mammalian glycans incorporate only the pyranose form of galactose (Galp), many pathogens, including Mycobacterium tuberculosis and Klebsiella pneumoniae, contain galactofuranose (Galf) residues in their cell envelope. Thus, glycan sequencing would benefit from methods to distinguish between pyranose and furanose isomers of different anomeric configurations. We used infrared multiple photon dissociation (IRMPD) spectroscopy with mass spectrometry (MS-IR) to differentiate between pyranose- and furanose-linked galactose residues. These targets pose a challenge for MS-IR because the saccharides lack basic groups, and galactofuranose residues are highly flexible. We postulated cationic groups that could complex through hydrogen bonding would offer a solution. Here, we present the first MS-IR analysis of hexose ammonium adducts. We compared their IR fingerprints with those of lithium adducts. We determined the diagnostic MS-IR signatures of the α- and β-anomers of galactose in furanose and pyranose forms. We also showed these signatures could be applied to disaccharides to assign galactose ring size. Our findings highlight the utility of MS-IR for analyzing the unique substructures that occur in bacterial glycans.

    Copyright © 2021 American Chemical Society

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. Add or change your institution or let them know you’d like them to include access.

    Supporting Information

    Click to copy section linkSection link copied!

    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/jacs.0c11919.

    • Additional figures, experimental procedures, synthesis of small molecules, and MS-IR analyses (PDF)

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    Click to copy section linkSection link copied!
    Citation Statements
    Explore this article's citation statements on scite.ai

    This article is cited by 15 publications.

    1. Ali H. Abikhodr, Stephan Warnke, Ahmed Ben Faleh, Thomas R. Rizzo. Combining Liquid Chromatography and Cryogenic IR Spectroscopy in Real Time for the Analysis of Oligosaccharides. Analytical Chemistry 2024, 96 (4) , 1462-1467. https://doi.org/10.1021/acs.analchem.3c03578
    2. Oznur Yeni, Simon Ollivier, Baptiste Moge, David Ropartz, Hélène Rogniaux, Laurent Legentil, Vincent Ferrières, Isabelle Compagnon. Ring-Size Memory of Galactose-Containing MS/MS Fragments: Application to the Detection of Galactofuranose in Oligosaccharides and Their Sequencing. Journal of the American Chemical Society 2023, 145 (28) , 15180-15187. https://doi.org/10.1021/jacs.3c01925
    3. Rianne E. van Outersterp, Pieter C. Kooijman, Jona Merx, Udo F.H. Engelke, Nematollah Omidikia, Mei-Lan H. Tonneijck, Kas J. Houthuijs, Giel Berden, Tessa M.A. Peters, Dirk J. Lefeber, Michel A. A. P. Willemsen, Jasmin Mecinovic, Jeroen J. Jansen, Karlien L.M. Coene, Ron A. Wevers, Thomas J. Boltje, Jos Oomens, Jonathan Martens. Distinguishing Oligosaccharide Isomers Using Far-Infrared Ion Spectroscopy: Identification of Biomarkers for Inborn Errors of Metabolism. Analytical Chemistry 2023, 95 (26) , 9787-9796. https://doi.org/10.1021/acs.analchem.3c00363
    4. Simon Ollivier, Laurent Legentil, Oznur Yeni, Louis-Philippe David, Vincent Ferrières, Isabelle Compagnon, Hélène Rogniaux, David Ropartz. Gas-Phase Behavior of Galactofuranosides upon Collisional Fragmentation: A Multistage High-Resolution Ion Mobility Study. Journal of the American Society for Mass Spectrometry 2023, 34 (4) , 627-639. https://doi.org/10.1021/jasms.2c00333
    5. Zhixin Xiong, Meixian Yang, Xiuting Chen, Yu Gong. Influence of Metal Coordination on the Gas-Phase Chemistry of the Positional Isomers of Fluorobenzoate Complexes. Journal of the American Society for Mass Spectrometry 2022, 33 (11) , 2181-2190. https://doi.org/10.1021/jasms.2c00236
    6. Robert P. Pellegrinelli, Lei Yue, Eduardo Carrascosa, Ahmed Ben Faleh, Stephan Warnke, Priyanka Bansal, Thomas R. Rizzo. A New Strategy Coupling Ion-Mobility-Selective CID and Cryogenic IR Spectroscopy to Identify Glycan Anomers. Journal of the American Society for Mass Spectrometry 2022, 33 (5) , 859-864. https://doi.org/10.1021/jasms.2c00043
    7. Dávid Szamosvári, Munhyung Bae, Sunghee Bang, Betsabeh Khoramian Tusi, Chelsi D. Cassilly, Sung-Moo Park, Daniel B. Graham, Ramnik J. Xavier, Jon Clardy. Lyme Disease, Borrelia burgdorferi, and Lipid Immunogens. Journal of the American Chemical Society 2022, 144 (6) , 2474-2478. https://doi.org/10.1021/jacs.1c12202
    8. Stephan Warnke, Ahmed Ben Faleh, Thomas R. Rizzo. Toward High-Throughput Cryogenic IR Fingerprinting of Mobility-Separated Glycan Isomers. ACS Measurement Science Au 2021, 1 (3) , 157-164. https://doi.org/10.1021/acsmeasuresciau.1c00018
    9. Marc Safferthal, Łukasz Polewski, Chun-Wei Chang, Kim Greis, Kevin Pagel. Cold-ion Spectroscopy of Carbohydrates. 2024, 76-94. https://doi.org/10.1039/9781839166433-00076
    10. Darren T. Gass, Ana V. Quintero, Jacob B. Hatvany, Elyssia S. Gallagher. Metal adduction in mass spectrometric analyses of carbohydrates and glycoconjugates. Mass Spectrometry Reviews 2024, 43 (4) , 615-659. https://doi.org/10.1002/mas.21801
    11. M. P. Dvores, P. Çarçabal, R. B. Gerber. Selective reactivity of glycosyl cation stereoisomers: the role of intramolecular hydrogen bonding. Physical Chemistry Chemical Physics 2023, 25 (39) , 26737-26747. https://doi.org/10.1039/D3CP03326K
    12. Min Kou, Young-Ho Oh, Sungyul Lee, Xianglei Kong. Distinguishing gas phase lactose and lactulose complexed with sodiated l -arginine by IRMPD spectroscopy and DFT calculations. Physical Chemistry Chemical Physics 2023, 25 (37) , 25116-25121. https://doi.org/10.1039/D3CP03406B
    13. Baptiste Moge, Oznur Yeni, Alicia Infantino, Isabelle Compagnon. CO2 laser enhanced rapid IRMPD spectroscopy for glycan analysis. International Journal of Mass Spectrometry 2023, 490 , 117071. https://doi.org/10.1016/j.ijms.2023.117071
    14. Kim Greis, Carla Kirschbaum, Gert von Helden, Kevin Pagel. Gas-phase infrared spectroscopy of glycans and glycoconjugates. Current Opinion in Structural Biology 2022, 72 , 194-202. https://doi.org/10.1016/j.sbi.2021.11.006
    15. Oznur Yeni, Baptiste Schindler, Baptiste Moge, Isabelle Compagnon. Rapid IRMPD (InfraRed multiple photon dissociation) analysis for glycomics. The Analyst 2022, 147 (2) , 312-317. https://doi.org/10.1039/D1AN01870A

    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2021, 143, 28, 10509–10513
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jacs.0c11919
    Published July 8, 2021
    Copyright © 2021 American Chemical Society

    Article Views

    2797

    Altmetric

    -

    Citations

    Learn about these metrics

    Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

    Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.

    The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.